Wikipedia - User contributions [en]

Methyl 2-acetamidoacrylate

2024-12-24T07:00:16Z

Leiem: added Category:Methyl esters using HotCat

{{Chembox
| ImageFile = AcetamidoacrylateMe ester.png
| ImageSize =
| ImageAlt =
| PIN = Methyl 2-acetamidoprop-2-enoate
| OtherNames = Methyl 2-(acetylamino)propenoate
|Section1={{Chembox Identifiers
| CASNo = 35356-70-8
| PubChem = 98644
| ChemSpiderID = 89087
| UNII = GT3ARJ50FG
| EC_number = 609-121-9
| StdInChI=1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
| StdInChIKey = SMWNFFKPVLVOQQ-UHFFFAOYSA-N
| SMILES = CC(=O)NC(=C)C(=O)OC
}}
|Section2={{Chembox Properties
| C=6|H=9|N=1|O=3
| MolarMass =
| Appearance = white solid
| Density =
| MeltingPtC = 75-76
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''Methyl 2-acetamidoacrylate''' is the [[organic compound]] with the formula CH2=C(NHC(O)CH3)CO2CH3. It is the [[methyl ester]] of an ''N''-[[acetyl]][[acrylic acid]], which in turn is a derivative of the unstable compound [[dehydroalanine]]. [[Acetylation]] of the [[amine]] in the latter compound prevents tautomerization. It is a white solid.

The compound can be prepared from methyl 2-acetamidopropionate (CH3CH(NHC(O)CH3)CO2CH3), i.e. the methyl ester of N-acetylalanine.<ref>{{cite journal|author=Kolar, A. J.|author2=Olsen, R. K.|title=A Convenient, Large-Scale Preparation of 2-Acetamidoacrylic Acid and Its Methyl Ester|journal=Synthesis|volume=1977|issue=7|year=1977|pages=457–9|doi=10.1055/s-1977-24439|s2cid=96352441 }}</ref> Methyl 2-acetamidoacrylate undergoes [[Michael reaction]]s, e.g. by thiolates.<ref>{{cite journal|author=Petracca, R.|author2=Bowen, K. A.|author3=McSweeney, L.|author4=O’Flaherty, S.|author5=Genna, V.|author6=Twamley, B.|author7=Devocelle, M.|author8=Scanlan, E. M.|title=Chemoselective Synthesis of N-Terminal Cysteinyl Thioesters via β,γ-C,S Thiol-Michael Addition|journal=Organic Letters|year=2019|volume=21|issue=9|pages=3281–3285|doi=10.1021/acs.orglett.9b01013|pmid=31017793|s2cid=131775844 |url=https://figshare.com/articles/journal_contribution/22787930 }}</ref>

==References==
{{Reflist}}

[[Category:Acetamides]]
[[Category:Methyl esters]]

Methyl nicotinate

2024-12-24T02:42:11Z

Leiem: removed Category:Nicotinates; added Category:Nicotinate esters using HotCat

{{distinguish|Menthyl nicotinate}}
{{Chembox

| ImageFile = Methyl nicotinate.svg
| ImageSize = 150px
| ImageAlt =

| IUPACName = Methyl pyridine-3-carboxylate
| OtherNames = Nicotinic acid methyl ester; Nikomet

| Section1 = {{Chembox Identifiers
| CASNo = 93-60-7
| PubChem = 7151
| UNII = 7B1AVU9DJN
| DrugBank = DB13882
| SMILES = COC(=O)C1=CN=CC=C1
}}
| Section2 = {{Chembox Properties
| C = 7 | H = 7 | N = 1 | O = 2
| Appearance =
| Density =
| MeltingPtC = 39
| MeltingPt_ref = <ref name=Merck>{{cite book | title = [[Merck Index]] | id = '''6014'''. Methyl nicotinate | edition = 11th | pages =6005-6006 }}</ref>
| BoilingPtC = 209
| BoilingPt_ref = <ref name=Merck/>
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Methyl nicotinate''' is a chemical compound with the molecular formula {{chem2|C7H7NO2}}. It is the [[methyl]] [[ester]] of [[nicotinic acid]] (niacin).

==Properties==
Methyl nicotinate is a white crystalline solid with a melting point of 39 °C.<ref name=Merck/> It is soluble in water, [[ethanol]], and [[benzene]].<ref name=Merck/>

==Uses==
Methyl nicotinate is a [[rubefacient]] and is used in some over-the-counter topical medical sprays, such as [[Ralgex]], for relief of muscle and joint pains.<ref>{{cite web | url = https://go.drugbank.com/drugs/DB13882 | title = Methyl nicotinate | work = [[DrugBank]] }}</ref>

==See also==
* [[Methyl isonicotinate]]
* [[Trigonelline]] (''N''-methyl nicotinate)

==References==
{{reflist}}

[[Category:Methyl esters]]
[[Category:Nicotinate esters]]

1,1-Dimethylurea

2024-12-23T08:08:59Z

Leiem:

{{Orphan|date=December 2024}}

{{chembox
|ImageFile = 1,1-Dimethylurea.svg
|IUPACName = 1,1-Dimethylurea
|OtherNames = ''N'',''N''-Dimethylurea
|Section1={{Chembox Identifiers
| CASNo = 598-94-7
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 11244
| PubChem = 11737
| UNII = I988R763P3
| StdInChI=1S/C3H8N2O/c1-5(2)3(4)6/h1-2H3,(H2,4,6)
| StdInChIKey = YBBLOADPFWKNGS-UHFFFAOYSA-N
| SMILES = CN(C)C(=O)N
}}
|Section2={{Chembox Properties
| C=3|H=8|N=2|O=1
}}
|Section8={{Chembox Related
| OtherCompounds = [[1,3-Dimethylurea]]
}}
}}

'''1,1-Dimethylurea''' ('''DMU''') is a [[urea]] derivative used as a [[polar solvent]] and a [[reagent]] in [[organic chemical|organic]] reactions. It is a solid, but forms a [[eutectic]] with a low [[melting point]] in combination with various [[hydroxylic]] additives that can serve as a [[environmentally sustainable]] solvent for various chemical reactions.<ref>{{cite journal |doi= 10.1016/j.tet.2014.11.024 |title= Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions |date= 2015 |last1= Kotha |first1= Sambasivarao |last2= Ali |first2= Rashid |last3= Srinivas |first3= Venu |last4= Krishna |first4= Nimita G. |journal= Tetrahedron |volume= 71 |pages= 129–138 }}</ref><ref>{{cite journal |doi= 10.1002/cctc.201402415 |title= Superparamagnetic CuFeO2 Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazo[1,2-''a'']pyridines |date= 2014 |last1= Lu |first1= Jun |last2= Li |first2= Xiao-Tang |last3= Ma |first3= Er-Qian |last4= Mo |first4= Li-Ping |last5= Zhang |first5= Zhan-Hui |journal= ChemCatChem |volume= 6 |issue= 10 |pages= 2854–2859 }}</ref><ref>{{cite journal |doi= 10.1039/b414515a |title= Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions |date= 2005 |last1= Imperato |first1= Giovanni |last2= Eibler |first2= Ernst |last3= Niedermaier |first3= Julia |last4= König |first4= Burkhard |journal= Chem. Commun. |issue= 9 |pages= 1170–1172 |pmid= 15726181 }}</ref><ref>{{cite journal |doi= 10.1039/B816551C |title= Organic reactions in low melting mixtures based on carbohydrates and L-carnitine—a comparison |date= 2009 |last1= Ilgen |first1= Florian |last2= König |first2= Burkhard |journal= Green Chemistry |volume= 11 |issue= 6 |page= 848 }}</ref> The un[[substituent|substituted]] nitrogen, as an [[amine]]-like region, can serve as a [[nucleophile]] for a wide range of reactions, including reaction with [[acyl halide]]s to form [[acylurea]]s,<ref>{{cite journal |doi= 10.1021/jm0498351 |title= Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives |date= 2004 |last1= Sobol |first1= Eyal |last2= Bialer |first2= Meir |last3= Yagen |first3= Boris |journal= Journal of Medicinal Chemistry |volume= 47 |issue= 17 |pages= 4316–4326 |pmid= 15294003 }}</ref> [[coupling reaction|coupling]] with [[vinyl halide]]s,<ref>{{cite journal |doi= 10.1002/ejoc.201403405 |title= Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1''H'')-pyrazinones |date= 2015 |last1= Belfrage |first1= Anna Karin |last2= Gising |first2= Johan |last3= Svensson |first3= Fredrik |last4= Åkerblom |first4= Eva |last5= Sköld |first5= Christian |last6= Sandström |first6= Anja |journal= European Journal of Organic Chemistry |issue= 5 |pages= 978–986 }}</ref> and [[multi-component reaction|multi-component]] [[condensation reaction]] with [[aldehyde]]s.<ref>{{cite journal |doi= 10.13040/IJPSR.0975-8232.9(8).3322-27 |date= 2018 |journal= International Journal of Pharmaceutical Sciences and Research |volume= 9 |issue= 8 |pages= 3322–3327 |first1= Anis |last1= Ahamed |first2= Ibrahim A. |last2= Arif |first3= Meera |last3= Moydeen |first4= Radhakrishnan Surendra |last4= Kumar |first5= Akbar |last5= Idhayadhulla |title= In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives }}</ref> The unsubstituted [[amide]]-like portion can undergo [[oxidative]] coupling with [[alkene]]s to give dihydro[[oxazole]]s.<ref>{{cite journal |doi= 10.1002/anie.201904662 |title= Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation |date= 2019 |last1= Wu |first1= Fan |last2= Alom |first2= Nur-E |last3= Ariyarathna |first3= Jeewani P. |last4= Naß |first4= Johannes |last5= Li |first5= Wei |journal= Angewandte Chemie International Edition |volume= 58 |issue= 34 |pages= 11676–11680 |pmid= 31211504 }}</ref>

== References ==
{{reflist}}

[[Category:Ureas]]
[[Category:Methyl compounds]]
[[Category:Amide solvents]]

{{organic-compound-stub}}

Template:Element-symbol-to-oxidation-state-data

2024-12-16T10:23:06Z

Leiem: add hexavalent nickel (Ref: J. Am. Chem. Soc. 2024, doi:10.1021/jacs.4c12125)

{{ {{{os-formatter|Element-symbol-to-oxidation-state-echo}}}
|symbol={{{symbol|}}}
|common={{#switch:{{{symbol|}}}
|H=−1, +1
|He=
|Li=+1
|Be=+2
|B=+3
|C=−4, −3, −2, −1, 0, +1, +2, +3, +4
|N=−3, +3, +5
|O=−2
|F=−1
|Ne=
|Na=+1
|Mg=+2
|Al=+3
|Si=−4, +4
|P=−3, +3, +5
|S=−2, +2, +4, +6
|Cl=−1, +1, +3, +5, +7
|Ar=
|K=+1
|Ca=+2
|Sc=+3
|Ti=+4
|V=+5
|Cr=+3, +6
|Mn=+2, +4, +7
|Fe=+2, +3
|Co=+2, +3
|Ni=+2
|Cu=+2
|Zn=+2
|Ga=+3
|Ge=−4, +2, +4
|As=−3, +3, +5
|Se=−2, +2, +4, +6
|Br=−1, +1, +3, +5
|Kr=+2
|Rb=+1
|Sr=+2
|Y=+3
|Zr=+4
|Nb=+5
|Mo=+4, +6
|Tc=+4, +7
|Ru=+3, +4
|Rh=+3
|Pd=0, +2, +4
|Ag=+1
|Cd=+2
|In=+3
|Sn=−4, +2, +4
|Sb=−3, +3, +5
|Te=−2, +2, +4, +6
|I=−1, +1, +3, +5, +7
|Xe=+2, +4, +6
|Cs=+1
|Ba=+2
|La=+3
|Ce=+3, +4
|Pr=+3
|Nd=+3
|Pm=+3
|Sm=+3
|Eu=+2, +3
|Gd=+3
|Tb=+3
|Dy=+3
|Ho=+3
|Er=+3
|Tm=+3
|Yb=+3
|Lu=+3
|Hf=+4
|Ta=+5
|W=+4, +6
|Re=+4, +7
|Os=+4
|Ir=+3, +4
|Pt=+2, +4
|Au=+3
|Hg=+1, +2
|Tl=+1, +3
|Pb=+2, +4
|Bi=+3
|Po=−2, +2, +4
|At=−1, +1
|Rn=
|Fr=+1
|Ra=+2
|Ac=+3
|Th=+4
|Pa=+5
|U=+6
|Np=+5
|Pu=+4
|Am=+3
|Cm=+3
|Bk=+3
|Cf=+3
|Es=+3
|Fm=+3
|Md=+3
|No=+3
|Lr=+3
|Rf=+4
|Db=
|Sg=
|Bh=
|Hs=
|Mt=
|Ds=
|Rg=
|Cn=
|Nh=
|Fl=
|Mc=
|Lv=
|Ts=
|Og=
|Uue=
|Ubn=
|Ubu=
|Ubb=
|Ubt=
|Ubq=
|Ubp=
|Ubh=

|#default={{#if:{{{symbol|}}}|{{error|[[:Template:Infobox element/symbol-to-oxidation-state]]: Symbol "{{{symbol|}}}" not known}}}}
}}
|notable={{#switch:{{{symbol|}}}

| H=
| He=0<ref>Disodium helide, (Na+)2He(e-)2, has been synthesized at high pressure, see {{cite journal |last1=Dong |first1=Xiao |last2=Oganov |first2=Artem R. |last3=Goncharov |first3=Alexander F. |last4=Stavrou |first4=Elissaios |last5=Lobanov |first5=Sergey |last6=Saleh |first6=Gabriele |last7=Qian |first7=Guang-Rui |last8=Zhu |first8=Qiang |last9=Gatti |first9=Carlo |last10=Deringer |first10=Volker L. |last11=Dronskowski |first11=Richard |last12=Zhou |first12=Xiang-Feng |last13=Prakapenka |first13=Vitali B. |last14=Konôpková |first14=Zuzana |last15=Popov |first15=Ivan A. |last16=Boldyrev |first16=Alexander I. |last17=Wang |first17=Hui-Tian |title=A stable compound of helium and sodium at high pressure |journal=[[Nature Chemistry]] |volume=9 |issue=5|pages=440–445 |date=6 February 2017 |doi=10.1038/nchem.2716 |pmid=28430195 |bibcode=2017NatCh...9..440D |arxiv=1309.3827 |s2cid=20459726}}</ref>

| Li= −1<ref>Li(–1) has been observed in the gas phase; see {{cite journal |author1=R. H. Sloane |author2=H. M. Love |title=Surface Formation of Lithium Negative Ions |journal=Nature |date=1947 |volume=159 |pages=302–303 |doi=10.1038/159302a0 |language=en}}</ref>
| Be= 0,<ref name=ZeroValentBeryllium>Be(0) has been observed; see {{cite web |title= Beryllium(0) Complex Found |url= https://www.chemistryviews.org/details/news/9426001/Beryllium0_Complex_Found.html |publisher= [[Chemistry Europe]] |date= 13 June 2016}}</ref> +1<ref>{{cite web|url=http://bernath.uwaterloo.ca/media/252.pdf|title=Beryllium: Beryllium(I) Hydride compound data|access-date=2007-12-10|publisher=bernath.uwaterloo.ca}}</ref>
| B=−5,<ref>B(−5) has been observed in Al3BC, see {{cite news|url=https://d-nb.info/995006210/34|first1=Melanie|last1=Schroeder|title=Eigenschaften von borreichen Boriden und Scandium-Aluminium-Oxid-Carbiden|page=139|language=de}}</ref> −1,<ref>B(−1) has been observed in [[magnesium diboride]] (MgB2), see {{cite book|url=https://books.google.com/books?id=2RgbAgAAQBAJ&pg=PA315|title=Chemical Structure and Reactivity: An Integrated Approach|first1=James|last1=Keeler|first2=Peter|last2=Wothers|publisher=Oxford University Press|year=2014|isbn=9780199604135}}</ref> 0,<ref>{{cite journal|doi=10.1126/science.1221138|title=Ambient-Temperature Isolation of a Compound with a Boron-Boron Triple Bond|year=2012|last1=Braunschweig|first1=H.|last2=Dewhurst|first2=R. D. |last3=Hammond|first3=K.|last4=Mies|first4=J.|last5=Radacki|first5=K.|last6=Vargas|first6=A.|journal=Science|volume=336|issue=6087|pages=1420–2|pmid=22700924|bibcode=2012Sci...336.1420B|s2cid=206540959}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref><ref>{{cite journal| url=http://bernath.uwaterloo.ca/media/125.pdf| title=Infrared Emission Spectroscopy of BF and AIF| author1=Zhang, K.Q.| author2=Guo, B.|author3=Braun, V.| author4=Dulick, M.| author5=Bernath, P.F.| journal=J. Molecular Spectroscopy| volume=170| issue=1| year=1995| page=82| doi=10.1006/jmsp.1995.1058|bibcode=1995JMoSp.170...82Z}}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| C=
| N=−2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>[[Tetrazole]]s contain a pair of double-bonded nitrogen atoms with oxidation state 0 in the ring. A Synthesis of the parent 1H-tetrazole, {{chem2|CH2N4}} (two atoms N(0)) is given in {{cite journal | last=Henry | first=Ronald A. | last2=Finnegan | first2=William G. | title=An Improved Procedure for the Deamination of 5-Aminotetrazole | journal=Journal of the American Chemical Society | volume=76 | issue=1 | date=1954 | issn=0002-7863 | doi=10.1021/ja01630a086 | pages=290–291}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| O= −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0, +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| F=
| Ne=0<ref>Ne(0) has been observed in Cr(CO)5Ne; see {{cite journal|last1=Perutz|first1=Robin N.|last2=Turner|first2=James J. |title=Photochemistry of the Group 6 hexacarbonyls in low-temperature matrices. III. Interaction of the pentacarbonyls with noble gases and other matrices|journal=Journal of the American Chemical Society|date=August 1975|volume=97|issue=17|pages=4791–4800 |doi=10.1021/ja00850a001}}</ref>

| Na=−1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0<ref>The compound [[NaCl]] has been shown in experiments to exists in several unusual [[stoichiometry|stoichiometries]] under high pressure, including Na3Cl in which contains a layer of sodium(0) atoms; see {{Cite journal |last1=Zhang |first1=W. |last2=Oganov |first2=A. R. |last3=Goncharov |first3=A. F. |last4=Zhu |first4=Q. |last5=Boulfelfel |first5=S. E. |last6=Lyakhov |first6=A. O. |last7=Stavrou |first7=E. |last8=Somayazulu |first8=M. |last9=Prakapenka |first9=V. B. |last10=Konôpková |first10=Z. |year=2013 |title=Unexpected Stable Stoichiometries of Sodium Chlorides |journal=Science |volume=342 |issue=6165 |pages=1502–1505 |arxiv=1310.7674 |bibcode=2013Sci...342.1502Z |doi=10.1126/science.1244989 |pmid=24357316|s2cid=15298372}}</ref>
| Mg= 0,<ref>Mg(0) has been synthesized in a compound containing a Na2Mg22+ cluster coordinated to a bulky organic ligand; see {{cite journal |first1=B. |last1=Rösch |first2=T. X. |last2=Gentner |first3=J. |last3=Eyselein |first4=J. |last4=Langer |first5=H. |last5=Elsen |first6=W. |last6=Li |first7=S. |last7=Harder |title=Strongly reducing magnesium(0) complexes |doi=10.1038/s41586-021-03401-w |journal=Nature |volume=592 |year=2021 |issue=7856 |pages=717–721 |pmid=33911274 |bibcode=2021Natur.592..717R |s2cid=233447380 |postscript=none}}</ref> +1<ref>{{cite journal|url=http://bernath.uwaterloo.ca/media/24.pdf| title=The spectrum of magnesium hydride |author=Bernath, P. F. |author2=Black, J. H. |author3=Brault, J. W. |name-list-style=amp |bibcode=1985ApJ...298..375B | doi=10.1086/163620
|journal=Astrophysical Journal|volume=298| year=1985| page=375}}. See also [[Low valent magnesium compounds]].</ref>
| Al=−2,<ref>Al(−2) has been observed in Sr14[Al4]2[Ge]3, see {{cite journal|last1=Wemdorff|first1=Marco|last2=Röhr|first2=Caroline|title=Sr14[Al4]2[Ge]3: Eine Zintl-Phase mit isolierten [Ge]4–- und [Al4]8–-Anionen / Sr14[Al4]2[Ge]3: A Zintl Phase with Isolated [Ge]4–- and [Al4]8– Anions|journal=Zeitschrift für Naturforschung B|language=de|volume=62|issue=10|year=2007|page=1227|doi=10.1515/znb-2007-1001|s2cid=94972243}}</ref> −1,<ref>Al(–1) has been reported in Na5Al5; see {{cite journal |author1=Haopeng Wang |author2=Xinxing Zhang |author3=Yeon Jae Ko |author4=Andrej Grubisic |author5=Xiang Li |author6=Gerd Ganteför |author7=Hansgeorg Schnöckel |author8=Bryan W. Eichhorn |author9=Mal-Soon Lee |author10=P. Jena |author11=Anil K. Kandalam |author12=Boggavarapu Kiran |author13=Kit H. Bowen |title=Aluminum Zintl anion moieties within sodium aluminum clusters |journal=The Journal of Chemical Physics |date=2014 |volume=140 |issue=5 |doi=10.1063/1.4862989 |language=en}}</ref> 0,<ref>Unstable carbonyl of Al(0) has been detected in reaction of [[Trimethylaluminum|Al2(CH3)6]] with carbon monoxide; see {{cite journal |first1=Ramiro |last1=Sanchez |first2=Caleb |last2=Arrington |first3=C. A. |last3=Arrington Jr. |title=Reaction of trimethylaluminum with carbon monoxide in low-temperature matrixes |journal=American Chemical Society |volume=111 |issue=25 |date=December 1, 1989 |page=9110-9111 |doi=10.1021/ja00207a023 |osti=6973516 |url=https://www.osti.gov/biblio/6973516-reaction-trimethylaluminum-carbon-monoxide-low-temperature-matrices}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref><ref>{{cite journal| title = Aluminum(I) and Gallium(I) Compounds: Syntheses, Structures, and Reactions|author1=Dohmeier, C. |author2=Loos, D. |author3=Schnöckel, H. | journal = Angewandte Chemie International Edition | year =1996| volume =35|issue=2 | pages =129–149| doi =10.1002/anie.199601291}}</ref> +2<ref>{{cite journal| author = Tyte, D. C. | title = Red (B2Π–A2σ) Band System of Aluminium Monoxide| doi = 10.1038/202383a0 | journal = Nature | volume = 202| issue = 4930 | year = 1964| page = 383 | bibcode=1964Natur.202..383T| s2cid = 4163250}}</ref>
| Si=−3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref name=ZeroValentTin>{{cite web |title=New Type of Zero-Valent Tin Compound |url= https://www.chemistryviews.org/details/news/9745121/New_Type_of_Zero-Valent_Tin_Compound.html |publisher=[[Chemistry Europe]] |date=27 August 2016}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref><ref>{{cite journal|author=Ram, R. S.|title=Fourier Transform Emission Spectroscopy of the A2D–X2P Transition of SiH and SiD|url=http://bernath.uwaterloo.ca/media/184.pdf |journal=J. Mol. Spectr. |volume=190|issue=2|pages=341–352|year=1998|pmid=9668026|display-authors=etal|doi=10.1006/jmsp.1998.7582}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| P = −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>{{cite journal|doi=10.1021/ja807828t|title=Carbene-Stabilized Diphosphorus|year=2008|last1=Wang|first1=Yuzhong|last2=Xie|first2=Yaoming|last3=Wei|first3=Pingrong|last4=King|first4=R. Bruce|last5=Schaefer|first5=Iii|last6=Schleyer|first6=Paul v. R.|last7=Robinson|first7=Gregory H.|journal=Journal of the American Chemical Society|volume=130|issue=45|pages=14970–1|pmid=18937460}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref><ref>{{cite journal|doi=10.1021/ic060186o|pmid=16903744|title=Phosphorus(I) Iodide: A Versatile Metathesis Reagent for the Synthesis of Low Oxidation State Phosphorus Compounds|year=2006|last1=Ellis|first1=Bobby D.|last2=MacDonald|first2=Charles L. B.|journal=Inorganic Chemistry|volume=45|issue=17|pages=6864–74}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| S= −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0, +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Cl= +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ar=0<ref>Ar(0) has been observed in [[argon fluorohydride]] (HArF) and ArCF22+, see {{cite journal |display-authors=4 |last1=Lockyear|first1=J.F. |last2=Douglas|first2=K. |last3=Price|first3=S.D. |last4=Karwowska|first4=M. |last5=Fijalkowski|first5=K.J. |last6=Grochala|first6=W. |last7=Remeš|first7=M. |last8=Roithová|first8=J. |last9=Schroder|first9=D. |name-list-style=amp |date=2010 |title=Generation of the ArCF22+ Dication |journal=[[Journal of Physical Chemistry Letters]] |volume=1 |page=358 |doi=10.1021/jz900274p}}</ref>

| K=−1<ref name="neg metals">{{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref>
| Ca=+1<ref name="West">{{cite journal|last1=Krieck|first1=Sven|last2=Görls|first2=Helmar|last3=Westerhausen|first3=Matthias|title=Mechanistic Elucidation of the Formation of the Inverse Ca(I) Sandwich Complex [(thf)3Ca(μ-C6H3-1,3,5-Ph3)Ca(thf)3] and Stability of Aryl-Substituted Phenylcalcium Complexes|journal=Journal of the American Chemical Society|volume=132|issue=35|pages=12492–12501|year=2010|pmid=20718434|doi=10.1021/ja105534w}}</ref>
| Sc= 0,<ref name="Cloke1991">{{cite journal |author=Cloke, F. Geoffrey N. |author2=Khan, Karl |author3=Perutz, Robin N. |name-list-style=amp |date=1991|title=η-Arene complexes of scandium(0) and scandium(II) |journal= J. Chem. Soc., Chem. Commun.|issue=19|pages=1372–1373|doi= 10.1039/C39910001372}}</ref> +1,<ref name="Smith">{{cite journal|title=Diatomic Hydride and Deuteride Spectra of the Second Row Transition Metals|first=R. E.|last=Smith | journal=Proceedings of the Royal Society of London. Series A, Mathematical and Physical Sciences|volume=332|pages=113–127|issue=1588|year=1973|doi=10.1098/rspa.1973.0015|bibcode=1973RSPSA.332..113S |s2cid=96908213}}</ref> +2<ref name="McGuire">{{cite journal|title=Preparation and Properties of Scandium Dihydride|first=Joseph C.|last=McGuire|author2=Kempter, Charles P.|journal=Journal of Chemical Physics|volume=33|issue=5|pages=1584–1585|year=1960|doi=10.1063/1.1731452|bibcode=1960JChPh..33.1584M }}</ref>
| Ti=−2,<ref>Ti(-2) is known in {{chem2|Ti(CO)6(2-)}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>{{cite journal |last1= Jilek |first1= Robert E. |last2= Tripepi |first2= Giovanna |last3= Urnezius |first3= Eugenijus |last4= Brennessel |first4= William W. |last5= Young |first5= Victor G. Jr. |last6= Ellis |first6= John E. |title= Zerovalent titanium–sulfur complexes. Novel dithiocarbamato derivatives of {{awrap|Ti(CO)6:[Ti(CO)4(S2CNR2)]−}} |journal= Chem. Commun. |issue= 25 |year= 2007 |pages= 2639–2641 |doi= 10.1039/B700808B |pmid= 17579764}}</ref> +1,<ref>{{cite journal|author=Andersson, N.|title=Emission spectra of TiH and TiD near 938 nm|journal=J. Chem. Phys.|volume=118|issue=8|year=2003|page=10543|doi=10.1063/1.1539848|bibcode=2003JChPh.118.3543A |display-authors=etal}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| V=−3,<ref>V(–3) is known in {{chem2|V(CO)5(3-)}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>V(0) is known in {{chem2|V(CO)6}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Cr=−4,<ref>Cr(–4) is known in {{chem2|Na4Cr(CO)4}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>Cr(0) is known in {{chem2|Cr(CO)6}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Mn=−3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −2,<ref>Mn(–2) is known in {{chem2|Mn(cod)2(2-)}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref><ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Fe=−2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +1,<ref>{{cite journal|last1=Ram |first1=R. S. |last2=Bernath |first2=P. F. |journal=Journal of Molecular Spectroscopy |volume=221| year=2003| page=261|bibcode=2003JMoSp.221..261R |doi=10.1016/S0022-2852(03)00225-X|title=Fourier transform emission spectroscopy of the g4Δ–a4Δ system of FeCl|issue=2}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref>{{cite journal|doi=10.1002/zaac.19824910109|title=Recent developments in the field of high oxidation states of transition elements in oxides stabilization of six-coordinated Iron(V)|year=1982|last1=Demazeau|first1=G.|journal=Zeitschrift für anorganische und allgemeine Chemie|volume=491|pages=60–66|last2=Buffat|first2=B.|last3=Pouchard|first3=M.|last4=Hagenmuller|first4=P.}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7<ref>{{cite journal|doi= 10.1039/C6CP06753K|pmid=27812577|title=Experimental and theoretical identification of the Fe(VII) oxidation state in FeO4−|year=2016|last1=Lu|first1=J.|journal=Physical Chemistry Chemical Physics|volume=18|issue=45|pages=31125–31131|last2=Jian|first2=J.|last3=Huang|first3=W.|last4=Lin|first4=H.|last5=Li|first5=J|last6=Zhou|first6=M.|bibcode=2016PCCP...1831125L}}</ref>
| Co=−3,<ref>Co(–3) is known in {{chem2|Na3Co(CO)3}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=greenwood>{{Greenwood&Earnshaw2nd|pages=1117–1119}}</ref>
| Ni=−2,<ref>Ni(–2) is known in {{chem2|Ni(COD)2(2-)}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>Ni(0) is known in {{chem2|Ni(CO)4}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> +1,<ref>{{cite journal| title=A Dinuclear Nickel(I) Dinitrogen Complex and its Reduction in Single-Electron Steps| journal=Angewandte Chemie International Edition| year=2009| volume=48 | issue=18| pages=3357–61| doi=10.1002/anie.200805862| last1=Pfirrmann| first1=Stefan| last2=Limberg| first2=Christian| last3=Herwig| first3=Christian| last4=Stößer| first4=Reinhard| last5=Ziemer| first5=Burkhard| pmid=19322853}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref>{{cite journal| title=A Stable Tetraalkyl Complex of Nickel(IV)| journal=Angewandte Chemie International Edition| year=2009| volume=48 | issue=2| pages=290–4| doi=10.1002/anie.200804435| last1=Carnes| first1=Matthew| last2=Buccella| first2=Daniela| last3=Chen| first3=Judy Y.-C.| last4=Ramirez| first4=Arthur P.| last5=Turro| first5=Nicholas J.| last6=Nuckolls| first6=Colin| last7=Steigerwald| first7=Michael| pmid=19021174}}</ref>, +6<ref>{{cite journal|author=Josef T. Boronski; Agamemnon E. Crumpton; Simon Aldridge|title=A Crystalline NiX6 Complex|journal=Journal of the American Chemical Society|year=2024|doi=10.1021/jacs.4c12125}}</ref>
| Cu=−2,<ref> Cu(−2) have been observed as dimeric anions [Cu4]2– in La2Cu2In; see {{cite journal|title=Late transition metal anions acting as p-metal elements|year=2008|author1=Changhoon Lee|author2=Myung-Hwan Whangbo|volume=10|issue=4|pages=444–449|journal=Solid State Sciences|doi=10.1016/j.solidstatesciences.2007.12.001|bibcode=2008SSSci..10..444K}}</ref> 0,<ref>{{cite journal|first1=Marc-Etienne|last1=Moret|first2=Limei|last2=Zhang|first3=Jonas C.|last3=Peters|title=A Polar Copper–Boron One-Electron σ-Bond|journal=J. Am. Chem. Soc|year=2013|volume=135|issue=10|pages=3792–3795|doi=10.1021/ja4006578|pmid=23418750|url=https://authors.library.caltech.edu/37931/ }}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Zn=−2,<ref> Zn(−2) have been observed (as dimeric and monomeric anions; dimeric ions were initially reported to be [T–T]2−, but later shown to be [T–T]4− for all these elements) in Ca5Zn3 (structure (AE2+)5(T–T)4−T2−⋅4e−); see {{cite journal|title=Late transition metal anions acting as p-metal elements|year=2008|author1=Changhoon Lee|author2=Myung-Hwan Whangbo|volume=10|issue=4|pages=444–449|journal=Solid State Sciences|doi=10.1016/j.solidstatesciences.2007.12.001|bibcode=2008SSSci..10..444K}} and {{cite journal|doi=10.1002/zaac.200900421|title=Analysis of Electronic Structures and Chemical Bonding of Metal-rich Compounds. 2. Presence of Dimer (T–T)4– and Isolated T2– Anions in the Polar Intermetallic Cr5B3-Type Compounds AE5T3 (AE = Ca, Sr; T = Au, Ag, Hg, Cd, Zn)|year=2010|author1=Changhoon Lee|author2=Myung-Hwan Whangbo|author3=Jürgen Köhler|volume=636|issue=1|pages=36–40|journal=Zeitschrift für Anorganische und Allgemeine Chemie}}</ref> 0,? +1<ref>Zn(I) has been reported in [[decamethyldizincocene]]; see {{cite journal |author1=Resa, I. |author2=Carmona, E. |author3=Gutierrez-Puebla, E. |author4=Monge, A. | title = Decamethyldizincocene, a Stable Compound of Zn(I) with a Zn-Zn Bond | journal = [[Science (journal)|Science]] | doi = 10.1126/science.1101356 | pmid = 15326350 | year = 2004 | volume = 305 | issue = 5687 | pages = 1136–8|bibcode=2004Sci...305.1136R |s2cid=38990338 }}</ref>
| Ga=−5,<ref name="Colture">{{cite thesis|url=http://www.uni-kassel.de/upress/online/frei/978-3-7281-2597-2.volltext.frei.pdf|author=Hofmann, Patrick |title=Colture. Ein Programm zur interaktiven Visualisierung von Festkörperstrukturen sowie Synthese, Struktur und Eigenschaften von binären und ternären Alkali- und Erdalkalimetallgalliden|page=72|language=de|date=1997|publisher=PhD Thesis, ETH Zurich|doi=10.3929/ethz-a-001859893|hdl=20.500.11850/143357 |isbn=978-3728125972}}</ref> −4,<ref name="Colture"/> −3,<ref>Ga(−3) has been observed in LaGa, see {{cite journal|lang=de|first1=Ines|last1=Dürr|first2=Britta|last2=Bauer|first3=Caroline|last3=Röhr|title=Lanthan-Triel/Tetrel-ide La(Al,Ga)''x''(Si,Ge)1-''x''. Experimentelle und theoretische Studien zur Stabilität intermetallischer 1:1-Phasen|journal=Z. Naturforsch.|year=2011|volume=66b|pages=1107–1121|url=http://www.znaturforsch.com/s66b/s66b1107.pdf}}</ref> −2,<ref name="Colture"/> −1,<ref>Ga(−1) has been observed in LiGa; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| pages=1185|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> 0,<ref>Ga(0) is known in [[gallium monoiodide]]; see {{Cite journal|last1=Widdifield|first1=Cory M.|last2=Jurca|first2=Titel|last3=Richeson|first3=Darrin S.|last4=Bryce|first4=David L.|date=2012-03-16|title=Using 69/71Ga solid-state NMR and 127I NQR as probes to elucidate the composition of "GaI"|url=http://www.sciencedirect.com/science/article/pii/S0277538712000101|journal=Polyhedron|language=en|volume=35|issue=1|pages=96–100|doi=10.1016/j.poly.2012.01.003|issn=0277-5387}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ge=−3,<ref name="germanides">Ge(−1), Ge(−2), Ge(−3), and Ge(–4) have been observed in [[germanide]]s; see {{cite book|publisher=Walter de Gruyter|year=1995|edition=101| pages=953–959|isbn=978-3-11-012641-9|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de|chapter=Germanium}}</ref> −2,<ref name="germanides">Ge(−1), Ge(−2), Ge(−3), and Ge(–4) have been observed in [[germanide]]s; see {{cite book|publisher=Walter de Gruyter|year=1995|edition=101| pages=953–959|isbn=978-3-11-012641-9|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de|chapter=Germanium}}</ref> −1,<ref name="germanides">Ge(−1), Ge(−2), Ge(−3), and Ge(–4) have been observed in [[germanide]]s; see {{cite book|publisher=Walter de Gruyter|year=1995|edition=101| pages=953–959|isbn=978-3-11-012641-9|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de|chapter=Germanium}}</ref> 0,<ref name=ZeroValentTin2>{{cite web |title=New Type of Zero-Valent Tin Compound |url= https://www.chemistryviews.org/details/news/9745121/New_Type_of_Zero-Valent_Tin_Compound.html |publisher=[[Chemistry Europe]] |date=27 August 2016}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| As=−2,<ref>As(−2) has been observed in CaAs; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| pages=829|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> −1,<ref>As(−1) has been observed in LiAs; see {{cite journal |author1=Reinhard Nesper |title=Structure and chemical bonding in zintl-phases containing lithium |journal=Progress in Solid State Chemistry |date=1990 |issue=1 |pages=1-45 |doi=10.1016/0079-6786(90)90006-2 |language=en}}</ref> 0,<ref>{{cite journal|doi=10.1002/chem.200902840|title=Carbene Stabilization of Diarsenic: From Hypervalency to Allotropy|year=2010|last1=Abraham|first1=Mariham Y.|last2=Wang|first2=Yuzhong|last3=Xie|first3=Yaoming|last4=Wei|first4=Pingrong|last5=Shaefer III|first5=Henry F.|last6=Schleyer|first6=P. von R.|last7=Robinson|first7=Gregory H.|journal=Chemistry: A European Journal|volume=16|issue=2|pages=432–5|pmid=19937872}}</ref> +1,<ref>{{cite journal|doi=10.1021/ic049281s|pmid=15360247|title=Stabilized Arsenic(I) Iodide: A Ready Source of Arsenic Iodide Fragments and a Useful Reagent for the Generation of Clusters|year=2004|last1=Ellis|first1=Bobby D.|last2=MacDonald|first2=Charles L. B.|journal=Inorganic Chemistry|volume=43|issue=19|pages=5981–6}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref>As(IV) has been observed in [[arsenic(IV) hydroxide]] (As(OH)4) and {{chem2|HAsO-}}; see {{cite journal|doi=10.1021/ic00313a007|title=Arsenic(IV). A pulse-radiolysis study|year=1989|last1=Kläning|first1=Ulrik K.|last2=Bielski|first2=Benon H. J.|last3=Sehested|first3=K.|journal=Inorganic Chemistry|volume=28|issue=14|pages=2717–24}}</ref>
| Se=−1,<ref>Se(−1) has been observed in diselenides({{chem2|Se2(2-)}}, such as [[disodium diselenide]] (Na2Se2); see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| pages=829|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}} and {{cite journal |author1=H. Föppl |author2=E. Busmann |author3=F.-K. Frorath |title=Die Kristallstrukturen von α-Na2S2 und K2S2, β-Na2S2 und Na2Se2 |journal=Zeitschrift für anorganische und allgemeine Chemie |date=1962 |volume=314 |issue=1 |pages=12-20 |doi=10.1002/zaac.19623140104 |language=de}}</ref> 0,<ref>A Se(0) atom has been identified using DFT in [ReOSe(2-pySe)3]; see {{cite journal|doi=10.1016/j.inoche.2014.04.003|title=Synthesis and structure of [ReOSe(2-Se-py)3]: A rhenium(V) complex with selenium(0) as a ligand|year=2014|last1=Cargnelutti|first1=Roberta|last2=Lang|first2=Ernesto S.|last3=Piquini|first3=Paulo|last4=Abram|first4=Ulrich|journal=Inorganic Chemistry Communications|volume=45|pages=48–50|issn=1387-7003}}</ref> +1,<ref>{{Greenwood&Earnshaw}}</ref> +3,<ref>Se(III) has been observed in Se2NBr3; see {{cite journal|title=Se2NBr3, Se2NCl5, Se2NCl−6: New Nitride Halides of Selenium(III) and Selenium(IV)| volume= 2|issue= 11|pages=1393–1396|year=1996|doi=10.1002/chem.19960021108|last1=Lau|first1=Carsten|last2=Neumüller|first2=Bernhard|last3=Vyboishchikov|first3=Sergei F.|last4=Frenking|first4=Gernot|last5=Dehnicke|first5=Kurt|last6=Hiller|first6=Wolfgang|last7=Herker|first7=Martin|journal=Chemistry: A European Journal}}</ref> +5?
| Br= +2,<ref>Br(II) is known to occur in bromine monoxide [[Radical (chemistry)|radical]]; see [https://pubs.acs.org/doi/10.1021/j100382a032 Kinetics of the bromine monoxide radical + bromine monoxide radical reaction]</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Kr=+1,?

| Rb=−1<ref>Rb(–1) is known in [[rubidides]]; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref>
| Sr=+1<ref>{{cite journal|url=http://bernath.uwaterloo.ca/media/149.pdf|title=High-Resolution Infrared Emission Spectrum of Strontium Monofluoride|journal=J. Molecular Spectroscopy| volume=175|issue=1|page=158|year=1996|doi=10.1006/jmsp.1996.0019|bibcode=1996JMoSp.175..158C|last1=Colarusso|first1=P.|last2=Guo|first2=B.|last3=Zhang|first3=K.-Q.|last4=Bernath|first4=P. F. }}</ref>
| Y= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,? +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Zr=−2,<ref>Zr(–2) is known in {{chem2|Zr(CO)6(2-)}}; see {{cite journal |author1=John E. Ellis |title=Adventures with Substances Containing Metals in Negative Oxidation States |journal=Inorganic Chemistry |date=2006 |volume=45 |issue=8 |doi=10.1021/ic052110i |language=en}}</ref> 0,<ref>Zr(0) occur in (η6-(1,3,5-''t''Bu)3C6H3)2Zr and [(η5-C5R5Zr(CO)4]−, see {{cite book|publisher=Elsevier Ltd.|year=2007|volume=4|pages=697–739|doi=10.1016/B0-08-045047-4/00062-5|title=Comprehensive Organometallic Chemistry III. From Fundamentals to Applications|first=P. J.|last=Chirik |author2=Bradley, C. A. |chapter=4.06 - Complexes of Zirconium and Hafnium in Oxidation States 0 to ii|isbn=9780080450476}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name="Calderazzo">{{Cite journal |last=Calderazzo |first=Fausto |last2=Pampaloni |first2=Guido |date=January 1992 |title=Organometallics of groups 4 and 5: Oxidation states II and lower |url=https://linkinghub.elsevier.com/retrieve/pii/0022328X92831263 |journal=Journal of Organometallic Chemistry |language=en |volume=423 |issue=3 |pages=307–328 |doi=10.1016/0022-328X(92)83126-3}}</ref><ref name="Ma">{{Cite journal |last1=Ma |first1=Wen |last2=Herbert |first2=F. William |last3=Senanayake |first3=Sanjaya D. |last4=Yildiz |first4=Bilge |date=2015-03-09 |title=Non-equilibrium oxidation states of zirconium during early stages of metal oxidation |url=https://pubs.aip.org/apl/article/106/10/101603/236409/Non-equilibrium-oxidation-states-of-zirconium |journal=Applied Physics Letters |language=en |volume=106 |issue=10 |doi=10.1063/1.4914180 |bibcode=2015ApPhL.106j1603M |issn=0003-6951|hdl=1721.1/104888 |hdl-access=free }}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Nb= −3,<ref>Nb(–3) occurs in {{chem2|Cs3Nb(CO)5}}; see {{cite journal |author1=John E. Ellis |title=Metal Carbonyl Anions: from [Fe(CO)4]2- to [Hf(CO)6]2- and Beyond† |journal=Organometallics |date=2003 |volume=22 |issue=17 |pages=3322–3338 |doi=10.1021/om030105l |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref name="lehrbuch">Nb(0) and Nb(I) has been observed in Nb(bpy)3 and CpNb(CO)4, respectively; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| pages=1554|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> +1,<ref name="lehrbuch">Nb(0) and Nb(I) has been observed in Nb(bpy)3 and CpNb(CO)4, respectively; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| pages=1554|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Mo= −4,<ref>Mo(–4) occurs in {{chem2|Na4Mo(CO)4}}; see {{cite journal |author1=John E. Ellis |title=Metal Carbonyl Anions: from [Fe(CO)4]2- to [Hf(CO)6]2- and Beyond† |journal=Organometallics |date=2003 |volume=22 |issue=17 |pages=3322–3338 |doi=10.1021/om030105l |language=en}}</ref> −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>Mo(0) occurs in [[molybdenum hexacarbonyl]]; see {{cite journal |author1=John E. Ellis |title=Metal Carbonyl Anions: from [Fe(CO)4]2- to [Hf(CO)6]2- and Beyond† |journal=Organometallics |date=2003 |volume=22 |issue=17 |pages=3322–3338 |doi=10.1021/om030105l |language=en}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Tc= −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ru= −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +8<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Rh= −3,<ref>Ellis J E. Highly Reduced Metal Carbonyl Anions: Synthesis, Characterization, and Chemical Properties. Adv. Organomet. Chem, 1990, 31: 1-51.</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,<ref>{{Greenwood&Earnshaw2nd|page=1140}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7<ref>Rh(VII) is known in the RhO3+ cation, see {{cite journal |title=The Highest Oxidation State of Rhodium: Rhodium(VII) in [RhO3]+ |journal=Angew. Chem. Int. Ed. |date=2022 |doi=10.1002/anie.202207688|last1=Da Silva Santos |first1=Mayara |last2=Stüker |first2=Tony |last3=Flach |first3=Max |last4=Ablyasova |first4=Olesya S. |last5=Timm |first5=Martin |last6=von Issendorff |first6=Bernd |last7=Hirsch |first7=Konstantin |last8=Zamudio‐Bayer |first8=Vicente |last9=Riedel |first9=Sebastian |last10=Lau |first10=J. Tobias |volume=61 |issue=38 |pages=e202207688 |pmid=35818987 |pmc=9544489 }}</ref>
| Pd= +1,<ref>Pd(I) is known in [Pd2]2+ compounds; see {{cite journal |author1=Christoph Fricke |author2=Theresa Sperger |author3=Marvin Mendel |author4=Franziska Schoenebeck |title=Catalysis with Palladium(I) Dimers |journal=Angewandte Chemie International Edition |date=2020 |volume=60 |issue=7 |doi=10.1002/anie.202011825 |language=en}}</ref> +3,<ref>Pd(III) has been observed; see {{cite book|last1=Powers |first1=D. C. |last2=Ritter |first2=T. |title=Higher Oxidation State Organopalladium and Platinum Chemistry |chapter=Palladium(III) in Synthesis and Catalysis |volume=35 |pages=129–156 |date=2011 |doi=10.1007/978-3-642-17429-2_6 |pmid=21461129 |chapter-url=http://www.chem.harvard.edu/groups/ritter/pdf/2011-129t.pdf |series=Topics in Organometallic Chemistry |isbn=978-3-642-17428-5 |url-status=dead |archive-url=https://web.archive.org/web/20130612065217/http://www.chem.harvard.edu/groups/ritter/pdf/2011-129t.pdf |archive-date=June 12, 2013 |pmc=3066514|bibcode=2011hoso.book..129P }}</ref> +5<ref>Palladium(V) has been identified in complexes with organosilicon compounds containing pentacoordinate palladium; see {{cite journal |first1=Shigeru |last1=Shimada |first2=Yong-Hua |last2=Li |first3=Yoong-Kee |last3=Choe |first4=Masato |last4=Tanaka |first5=Ming |last5=Bao |first6=Tadafumi |last6=Uchimaru |title=Multinuclear palladium compounds containing palladium centers ligated by five silicon atoms |doi=10.1073/pnas.0700450104 |journal=Proceedings of the National Academy of Sciences |volume=104 |year=2007 |issue=19 |pages=7758–7763|pmid=17470819 |pmc=1876520 |doi-access=free }}</ref>
| Ag= −2,<ref>Ag(−2) have been observed as dimeric and monomeric anions in Ca5Ag3, (structure (Ca2+)5(Ag–Ag)4−Ag2−⋅4e−); see {{cite journal|doi=10.1002/zaac.200900421|title=Analysis of Electronic Structures and Chemical Bonding of Metal-rich Compounds. 2. Presence of Dimer (T–T)4– and Isolated T2– Anions in the Polar Intermetallic Cr5B3-Type Compounds AE5T3 (AE = Ca, Sr; T = Au, Ag, Hg, Cd, Zn)|year=2010|author1=Changhoon Lee|author2=Myung-Hwan Whangbo|author3=Jürgen Köhler|volume=636|issue=1|pages=36–40|journal=Zeitschrift für Anorganische und Allgemeine Chemie}}</ref> −1,<ref>The Ag− ion has been observed in metal ammonia solutions: see {{cite journal|doi=10.1021/ic000333x|title=Metal Ammonia Solutions: Solutions Containing Argentide Ions|year=2001|last1=Tran|first1=N. E.|last2=Lagowski|first2=J. J.|journal=Inorganic Chemistry|volume=40|issue=5|pages=1067–68}}</ref> 0,<ref>Ag(0) has been observed in carbonyl complexes in low-temperature matrices: see {{cite journal|doi=10.1021/ja00427a018|title=Synthesis using metal vapors. Silver carbonyls. Matrix infrared, ultraviolet-visible, and electron spin resonance spectra, structures, and bonding of silver tricarbonyl, silver dicarbonyl, silver monocarbonyl, and disilver hexacarbonyl|year=1976|last1=McIntosh|first1=D.|last2=Ozin|first2=G. A.|journal=J. Am. Chem. Soc.|volume=98|issue=11|pages=3167–75}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Cd= −2,<ref name="MetalAnions">Cd(−2) have been observed (as dimeric and monomeric anions; dimeric ions were initially reported to be [T–T]2−, but later shown to be [T–T]4−) in Sr5Cd3; see {{cite journal|doi=10.1002/zaac.200900421|title=Analysis of Electronic Structures and Chemical Bonding of Metal-rich Compounds. 2. Presence of Dimer (T–T)4– and Isolated T2– Anions in the Polar Intermetallic Cr5B3-Type Compounds AE5T3 (AE = Ca, Sr; T = Au, Ag, Hg, Cd, Zn)|year=2010|author1=Changhoon Lee|author2=Myung-Hwan Whangbo|author3=Jürgen Köhler|volume=636|issue=1|pages=36–40|journal=Zeitschrift für Anorganische und Allgemeine Chemie}}</ref> +1<ref>Cd(I) has been observed in [[cadmium(I) tetrachloroaluminate]] (Cd2(AlCl4)2); see {{cite book|publisher= Walter de Gruyter|year= 1985|edition= 91–100|pages= 1056–1057|isbn= 978-3-11-007511-3|title= Lehrbuch der Anorganischen Chemie|last1= Holleman|first1= Arnold F.|last2= Wiberg|first2=Egon |last3=Wiberg |first3=Nils |language= de|chapter= Cadmium}}</ref>
| In= −5,<ref>{{cite journal|doi=10.1021/ic951378e|title=Synthesis, Structure, and Bonding of Two Lanthanum Indium Germanides with Novel Structures and Properties|year=1996|last1=Guloy|first1=A. M.|last2=Corbett|first2=J. D.|journal=Inorganic Chemistry|volume=35|issue=9|pages=2616–22|pmid=11666477}}</ref> −2,<ref>In(−2) has been observed in Na2In, see [https://books.google.com/books?id=v-04Kn758yIC&pg=PA69&lpg=PA69&dq=zintl+anions+Na2In&source=bl&ots=aXLYIpkfYq&sig=Mqh8WdnvGOt2J2OPVLNqn79YVyk&hl=ru&sa=X&ei=XNDkVNeSJeXOyQOb8oBA&ved=0CBsQ6AEwADgK#v=onepage&q&f=false], p. 69.</ref> −1,<ref>In(−1) has been observed in NaIn; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102|page=1185|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> 0,<ref>Unstable In(0) carbonyls and clusters have been detected, see [https://www.researchgate.net/profile/Anthony-Downs-2/publication/6589844_Development_of_the_Chemistry_of_Indium_in_Formal_Oxidation_States_Lower_than_3/links/5a82db2a0f7e9bda869fb52c/Development-of-the-Chemistry-of-Indium-in-Formal-Oxidation-States-Lower-than-3.pdf?origin=publication_detail], p. 6.</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Sn= −3,<ref>Sn(−3) has been observed in [Sn2]6−, e.g. in (Ba2)4+(Mg4)8+Sn4−(Sn2)6−Sn2− (with square (Sn2−)n sheets), see {{cite journal |last1=Papoian |first1=Garegin A. |last2=Hoffmann |first2=Roald |year=2000 |title=Hypervalent Bonding in One, Two, and Three Dimensions: Extending the Zintl–Klemm Concept to Nonclassical Electron-Rich Networks |journal=Angew. Chem. Int. Ed. |volume=2000 |issue= 39|pages=2408–2448 |url=https://www.researchgate.net/publication/12379848 |access-date=2015-02-23 |doi=10.1002/1521-3773(20000717)39:14<2408::aid-anie2408>3.0.co;2-u|pmid=10941096 }}</ref> −2,<ref>Sn(−2) has been observed in SrSn; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| page=1007|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> −1,<ref>Sn(−1) has been observed in CsSn; see {{cite book|publisher=Walter de Gruyter|year=2008|edition=102| page=1007|isbn=9783110206845|title=Lehrbuch der Anorganischen Chemie|first=Arnold F.|last=Holleman |author2=Wiberg, Egon |author3=Wiberg, Nils|language=de}}</ref> 0,<ref name=ZeroValentTin3>{{cite web |title=New Type of Zero-Valent Tin Compound |url= https://www.chemistryviews.org/details/news/9745121/New_Type_of_Zero-Valent_Tin_Compound.html |publisher=[[Chemistry Europe]] |date=27 August 2016}}</ref> +1,<ref>{{cite web|title=HSn|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C13940255&Units=SI|work=NIST Chemistry WebBook|publisher=National Institute of Standards and Technology|access-date=23 January 2013}}</ref> +3<ref>{{cite web|title=SnH3|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=B1001467&Units=SI|work=NIST Chemistry WebBook|publisher=National Institure of Standards and Technology|access-date=23 January 2013}}</ref>
| Sb= −2,<ref name="sbanion">Sb(−2) and Sb(−1) has been observed in [Sb2]4− and 1∞[Sbn]n−, respectively; see {{cite journal |last1=Boss |first1=Michael |last2=Petri |first2=Denis |last3=Pickhard |first3=Frank |last4=Zönnchen |first4=Peter |last5=Röhr |first5=Caroline |year=2005 |title=Neue Barium-Antimonid-Oxide mit den Zintl-Ionen [Sb]3−, [Sb2]4− und 1∞[Sbn]n− / New Barium Antimonide Oxides containing Zintl Ions [Sb]3−, [Sb2]4− and 1∞[Sbn]n− |journal=Zeitschrift für Anorganische und Allgemeine Chemie |volume=631 |issue= 6–7|pages=1181–1190 |language=de |doi= 10.1002/zaac.200400546}}</ref> −1,<ref name="sbanion">Sb(−2) and Sb(−1) has been observed in [Sb2]4− and 1∞[Sbn]n−, respectively; see {{cite journal |last1=Boss |first1=Michael |last2=Petri |first2=Denis |last3=Pickhard |first3=Frank |last4=Zönnchen |first4=Peter |last5=Röhr |first5=Caroline |year=2005 |title=Neue Barium-Antimonid-Oxide mit den Zintl-Ionen [Sb]3−, [Sb2]4− und 1∞[Sbn]n− / New Barium Antimonide Oxides containing Zintl Ions [Sb]3−, [Sb2]4− and 1∞[Sbn]n− |journal=Zeitschrift für Anorganische und Allgemeine Chemie |volume=631 |issue= 6–7|pages=1181–1190 |language=de |doi= 10.1002/zaac.200400546}}</ref> 0,<ref>{{cite news|url=https://pdfs.semanticscholar.org/8817/39f9dfc007d7f77dd7baa63fe12e6079f8ef.pdf|author=Anastas Sidiropoulos|title=Studies of N-heterocyclic Carbene (NHC) Complexes of the Main Group Elements|year=2019 |page=39|doi=10.4225/03/5B0F4BDF98F60|s2cid=132399530}}
</ref> +1,<ref>Sb(I) have been observed in [[organoantimony compounds]]; see {{cite journal |last1=Šimon |first1=Petr |last2=de Proft |first2=Frank |last3=Jambor |first3=Roman |last4=Růžička |first4=Aleš |last5=Dostál |first5=Libor |year=2010 |title=Monomeric Organoantimony(I) and Organobismuth(I) Compounds Stabilized by an NCN Chelating Ligand: Syntheses and Structures |journal=Angewandte Chemie International Edition |volume=49 |issue=32 |pages=5468–5471 |doi= 10.1002/anie.201002209|pmid=20602393}}</ref> +2,? +4<ref>Sb(IV) has been observed in {{chem2|[SbCl6](2-)}}, see {{cite journal|doi=10.1246/bcsj.73.1599|title=Production of Sb(IV) Chloro Complex by Flash Photolysis of the Corresponding Sb(III) and Sb(V) Complexes in CH3CN and CHCl3|year=2000|author1=Nobuyoshi Shinohara|author2=Masaaki Ohsima|journal=Bulletin of the Chemical Society of Japan|volume=73|issue=7|pages=1599–1604}}</ref>
| Te= −1,? 0,? +1,? +3,? +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| I= +2,<ref>I(II) is known to exist in monoxide (IO); see {{cite journal|last1=Nikitin|first1=I V|title=Halogen monoxides|journal=Russian Chemical Reviews|date=31 August 2008|volume=77|issue=8|pages=739–749|doi=10.1070/RC2008v077n08ABEH003788|bibcode=2008RuCRv..77..739N|s2cid=250898175 }}</ref> +4,? +6?
| Xe= 0,<ref>Xe(0) has been observed in [[tetraxenonogold(II)]] (AuXe42+).</ref> +8<ref name="Harding-2002">{{cite book|author=Harding, Charlie|author2=Johnson, David Arthur|author3= Janes, Rob |title = Elements of the ''p'' block |pages=93–94|publisher=Royal Society of Chemistry |location=Great Britain|date=2002 |isbn=0-85404-690-9 |url= https://books.google.com/books?id=W0HW8wgmQQsC&pg=PA93}}</ref>

| Cs=−1<ref name="caeside2">{{cite journal|journal = [[Angewandte Chemie|Angewandte Chemie International Edition]]|year = 1979|first = J. L.|last = Dye|title = Compounds of Alkali Metal Anions|volume = 18|issue = 8|pages = 587–598|doi = 10.1002/anie.197905871}}</ref>
| Ba=+1<ref>{{cite journal | doi=10.1021/acs.chemmater.8b03421 | title=A New and Facile Route Using Electride Solutions to Intercalate Alkaline Earth Ions into Graphite | year=2018 | last1=Xu | first1=Wei | last2=Lerner | first2=Michael M. | journal=Chemistry of Materials | volume=30 | issue=19 | pages=6930–6935 | s2cid=105295721 }}</ref>
| La= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref name=LnI>La(I), Pr(I), Tb(I), Tm(I), and Yb(I) have been observed in MB8− clusters; see {{cite journal|title=Monovalent lanthanide(I) in borozene complexes |journal=Nature Communications |volume=12 |page=6467 |year=2021 |last1=Li |first1=Wan-Lu |doi=10.1038/s41467-021-26785-9 |last2=Chen |first2=Teng-Teng |last3=Chen |first3=Wei-Jia |last4=Li |first4=Jun |last5=Wang |first5=Lai-Sheng|issue=1 |pmid=34753931 |pmc=8578558 }}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ce= +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Pr= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref>{{cite journal|title=Lanthanides with Unusually Low Oxidation States in the PrB3– and PrB4– Boride Clusters|journal=Inorganic Chemistry|volume=58|issue=1|pages=411–418|last1=Chen|first1=Xin|display-authors=etal|date=2019-12-13|doi=10.1021/acs.inorgchem.8b02572|pmid=30543295|s2cid=56148031 }}</ref> +2,<ref name="Lanthanides">All the [[lanthanide]]s, except Pm, in the +2 oxidation state have been observed in organometallic molecular complexes, see [http://cen.acs.org/articles/91/i24/Lanthanides-Topple-Assumptions.html Lanthanides Topple Assumptions] and {{cite journal|doi=10.1002/anie.201311325|title=All the Lanthanides Do It and Even Uranium Does Oxidation State +2|year=2014|last1=Meyer|first1=G.|journal=Angewandte Chemie International Edition|volume=53|issue=14|pages=3550–51|pmid=24616202}}. Additionally, all the [[lanthanide]]s (La–Lu) form dihydrides (LnH2), dicarbides (LnC2), monosulfides (LnS), monoselenides (LnSe), and monotellurides (LnTe), but for most elements these compounds have Ln3+ ions with electrons delocalized into conduction bands, e. g. Ln3+(H−)2(e−).</ref> +4,? +5
| Nd= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4
| Pm= +2?
| Sm= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref>SmB6- cluster anion has been reported and contains Sm in rare oxidation state of +1; see {{cite journal| title=SmB6– Cluster Anion: Covalency Involving f Orbitals
|first1=J. Robinson |last1=Paul |first2=Zhang |last2=Xinxing |first3=McQueen |last3=Tyrel |first4=H. Bowen |last4=Kit |first5=N. Alexandrova |last5=Anastassia |journal=J. Phys. Chem. A 2017,? 121,? 8,? 1849–1854 |year = 2017|volume = 121|issue = 8|pages = 1849–1854|doi=10.1021/acs.jpca.7b00247 |pmid=28182423 |s2cid=3723987 |url=https://pubs.acs.org/doi/abs/10.1021/acs.jpca.7b00247#}}.</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Eu= 0<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref>
| Gd= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Tb= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref name=LnI>La(I), Pr(I), Tb(I), Tm(I), and Yb(I) have been observed in MB8− clusters; see {{cite journal|title=Monovalent lanthanide(I) in borozene complexes |journal=Nature Communications |volume=12 |page=6467 |year=2021 |last1=Li |first1=Wan-Lu |doi=10.1038/s41467-021-26785-9 |last2=Chen |first2=Teng-Teng |last3=Chen |first3=Wei-Jia |last4=Li |first4=Jun |last5=Wang |first5=Lai-Sheng|issue=1 |pmid=34753931 |pmc=8578558 }}</ref> +2,<ref name="Lanthanides">All the [[lanthanide]]s, except Pm, in the +2 oxidation state have been observed in organometallic molecular complexes, see [http://cen.acs.org/articles/91/i24/Lanthanides-Topple-Assumptions.html Lanthanides Topple Assumptions] and {{cite journal|doi=10.1002/anie.201311325|title=All the Lanthanides Do It and Even Uranium Does Oxidation State +2|year=2014|last1=Meyer|first1=G.|journal=Angewandte Chemie International Edition|volume=53|issue=14|pages=3550–51|pmid=24616202}}. Additionally, all the [[lanthanide]]s (La–Lu) form dihydrides (LnH2), dicarbides (LnC2), monosulfides (LnS), monoselenides (LnSe), and monotellurides (LnTe), but for most elements these compounds have Ln3+ ions with electrons delocalized into conduction bands, e. g. Ln3+(H−)2(e−).</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Dy= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4
| Ho= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +2<ref name="Lanthanides">All the [[lanthanide]]s, except Pm, in the +2 oxidation state have been observed in organometallic molecular complexes, see [http://cen.acs.org/articles/91/i24/Lanthanides-Topple-Assumptions.html Lanthanides Topple Assumptions] and {{cite journal|doi=10.1002/anie.201311325|title=All the Lanthanides Do It and Even Uranium Does Oxidation State +2|year=2014|last1=Meyer|first1=G.|journal=Angewandte Chemie International Edition|volume=53|issue=14|pages=3550–51|pmid=24616202}}. Additionally, all the [[lanthanide]]s (La–Lu) form dihydrides (LnH2), dicarbides (LnC2), monosulfides (LnS), monoselenides (LnSe), and monotellurides (LnTe), but for most elements these compounds have Ln3+ ions with electrons delocalized into conduction bands, e. g. Ln3+(H−)2(e−).</ref>
| Er= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +2<ref name="Lanthanides">All the [[lanthanide]]s, except Pm, in the +2 oxidation state have been observed in organometallic molecular complexes, see [http://cen.acs.org/articles/91/i24/Lanthanides-Topple-Assumptions.html Lanthanides Topple Assumptions] and {{cite journal|doi=10.1002/anie.201311325|title=All the Lanthanides Do It and Even Uranium Does Oxidation State +2|year=2014|last1=Meyer|first1=G.|journal=Angewandte Chemie International Edition|volume=53|issue=14|pages=3550–51|pmid=24616202}}. Additionally, all the [[lanthanide]]s (La–Lu) form dihydrides (LnH2), dicarbides (LnC2), monosulfides (LnS), monoselenides (LnSe), and monotellurides (LnTe), but for most elements these compounds have Ln3+ ions with electrons delocalized into conduction bands, e. g. Ln3+(H−)2(e−).</ref>
| Tm= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref name=LnI>La(I), Pr(I), Tb(I), Tm(I), and Yb(I) have been observed in MB8− clusters; see {{cite journal|title=Monovalent lanthanide(I) in borozene complexes |journal=Nature Communications |volume=12 |page=6467 |year=2021 |last1=Li |first1=Wan-Lu |doi=10.1038/s41467-021-26785-9 |last2=Chen |first2=Teng-Teng |last3=Chen |first3=Wei-Jia |last4=Li |first4=Jun |last5=Wang |first5=Lai-Sheng|issue=1 |pmid=34753931 |pmc=8578558 }}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Yb= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +1,<ref name=LnI>La(I), Pr(I), Tb(I), Tm(I), and Yb(I) have been observed in MB8− clusters; see {{cite journal|title=Monovalent lanthanide(I) in borozene complexes |journal=Nature Communications |volume=12 |page=6467 |year=2021 |last1=Li |first1=Wan-Lu |doi=10.1038/s41467-021-26785-9 |last2=Chen |first2=Teng-Teng |last3=Chen |first3=Wei-Jia |last4=Li |first4=Jun |last5=Wang |first5=Lai-Sheng|issue=1 |pmid=34753931 |pmc=8578558 }}</ref> +2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Lu= 0,<ref name="Cloke1993">Yttrium and all lanthanides except Ce and Pm have been observed in the oxidation state 0 in bis(1,3,5-tri-t-butylbenzene) complexes, see {{cite journal |journal=Chem. Soc. Rev. |date=1993 |volume=22 |pages=17–24 |first=F. Geoffrey N. |last=Cloke |title=Zero Oxidation State Compounds of Scandium, Yttrium, and the Lanthanides |doi=10.1039/CS9932200017}} and {{cite journal|last1=Arnold|first1=Polly L.|last2=Petrukhina|first2=Marina A.|last3=Bochenkov|first3=Vladimir E.|last4=Shabatina|first4=Tatyana I.|last5=Zagorskii|first5=Vyacheslav V.|last6=Cloke|first9=F. Geoffrey N.|date=2003-12-15|title=Arene complexation of Sm, Eu, Tm and Yb atoms: a variable temperature spectroscopic investigation|journal=Journal of Organometallic Chemistry|volume=688|issue=1–2|pages=49–55|doi=10.1016/j.jorganchem.2003.08.028}}</ref> +2<ref name="Lanthanides">All the [[lanthanide]]s, except Pm, in the +2 oxidation state have been observed in organometallic molecular complexes, see [http://cen.acs.org/articles/91/i24/Lanthanides-Topple-Assumptions.html Lanthanides Topple Assumptions] and {{cite journal|doi=10.1002/anie.201311325|title=All the Lanthanides Do It and Even Uranium Does Oxidation State +2|year=2014|last1=Meyer|first1=G.|journal=Angewandte Chemie International Edition|volume=53|issue=14|pages=3550–51|pmid=24616202}}. Additionally, all the [[lanthanide]]s (La–Lu) form dihydrides (LnH2), dicarbides (LnC2), monosulfides (LnS), monoselenides (LnSe), and monotellurides (LnTe), but for most elements these compounds have Ln3+ ions with electrons delocalized into conduction bands, e. g. Ln3+(H−)2(e−).</ref>
| Hf= −2,<ref>Hf(–2) occurs in {{chem2|Hf(CO)6(2-)}}; see {{cite journal |author1=John E. Ellis |title=Metal Carbonyl Anions: from [Fe(CO)4]2- to [Hf(CO)6]2- and Beyond† |journal=Organometallics |date=2003 |volume=22 |issue=17 |pages=3322–3338 |doi=10.1021/om030105l |language=en}}</ref> 0,<ref>Hf(0) occur in (η6-(1,3,5-''t''Bu)3C6H3)2Hf and [(η5-C5R5Hf(CO)4]−, see {{cite book|publisher=Elsevier Ltd.|year=2007|volume=4|pages=697–739|doi=10.1016/B0-08-045047-4/00062-5|title=Comprehensive Organometallic Chemistry III. From Fundamentals to Applications|first=P. J.|last=Chirik |author2=Bradley, C. A. |chapter=4.06 - Complexes of Zirconium and Hafnium in Oxidation States 0 to ii|isbn=9780080450476}}</ref> +1,<ref>Hf(I) has been observed in hafnium monobromide (HfBr), see {{cite journal
| title= Кристаллическое строение и термодинамические характеристики монобромидов циркония и гафния / Crystal structure and thermodynamic characteristics of monobromides of zirconium and hafnium
| last1= Marek | first1= G.S. | last2= Troyanov | first2= S.I. | last3= Tsirel'nikov | first3= V.I. | journal= Журнал неорганической химии / Russian Journal of Inorganic Chemistry | year= 1979 | volume= 24 | issue= 4 | pages= 890–893 | language= ru | url= https://inis.iaea.org/search/search.aspx?orig_q=RN:11520917}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ta= −3,<ref>Ta(–3) occurs in {{chem2|Ta(CO)5(3-)}}; see {{cite journal |author1=John E. Ellis |title=Metal Carbonyl Anions: from [Fe(CO)4]2- to [Hf(CO)6]2- and Beyond† |journal=Organometallics |date=2003 |volume=22 |issue=17 |pages=3322–3338 |doi=10.1021/om030105l |language=en}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,? +1,? +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| W= −4,? −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,? +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Re= −3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,? +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Os= −4,? −2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −1,? 0,? +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +8<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Ir= −3,? −2,? −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0,? +1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7,? +8,? +9<ref name=IrIX>{{cite journal |last1=Wang |first1=Guanjun |last2=Zhou |first2=Mingfei |last3=Goettel |first3=James T. |last4=Schrobilgen |first4=Gary G. |last5=Su |first5=Jing |last6=Li |first6=Jun |last7=Schlöder |first7=Tobias |last8=Riedel |first8=Sebastian |date=2014 |title=Identification of an iridium-containing compound with a formal oxidation state of IX |journal=Nature |volume=514 |issue=7523 |pages=475–477 |doi=10.1038/nature13795 |pmid=25341786|bibcode=2014Natur.514..475W |s2cid=4463905 }}</ref>
| Pt= −3,? −2,? −1,? 0,? +1,? +3,? +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Au= −3,? −2,? −1,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> 0, +1,<ref>{{cite journal |doi= 10.1002/(SICI)1521-3773(19991102)38:21<3194::AID-ANIE3194>3.0.CO;2-O |title= Gold(I) and Gold(0) Complexes of Phosphinine‐Based Macrocycles|first1=Nicolas |last1= Mézaille |first2=Narcis |last2=Avarvari |first3=Nicole |last3=Maigrot|first4=Louis |last4=Ricard|first5=François |last5=Mathey|first6=Pascal |last6=Le Floch|first7=Laurent|last7=Cataldo|first8=Théo|last8=Berclaz|first9=Michel|last9=Geoffroy|journal= Angewandte Chemie International Edition|year= 1999 |volume= 38|issue= 21|pages= 3194–3197|pmid= 10556900}}</ref> +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Hg= −2<ref name="Brauer-1936">{{Cite journal |last=Brauer |first=G. |last2=Haucke |first2=W. |date=1936-06-01 |title=Kristallstruktur der intermetallischen Phasen MgAu und MgHg |url=https://www.degruyter.com/document/doi/10.1515/zpch-1936-3327/html |journal=Zeitschrift für Physikalische Chemie |language=en |volume=33B |issue=1 |pages=304–310 |doi=10.1515/zpch-1936-3327 |issn=2196-7156 |quote=MgHg then lends itself to an oxidation state of +2 for Mg and -2 for Hg because it consists entirely of these polar bonds with no evidence of electron unpairing. (translated)}}</ref>
| Tl= −5,<ref>{{cite journal|doi=10.1021/ic960014z|title=Na23K9Tl15.3: An Unusual Zintl Compound Containing Apparent Tl57−, Tl48−, Tl37−, and Tl5− Anions|year=1996|last1=Dong|first1=Z.-C.|last2=Corbett|first2=J. D.|journal=Inorganic Chemistry|volume=35|issue=11|pages=3107–12|pmid=11666505 }}</ref> −2,? −1,? +2?
| Pb= −4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −2,? −1,? 0,<ref>Pb(0) carbonyls have been observered in reaction between lead atoms and [[carbon monoxide]]; see {{cite journal|url=https://aip.scitation.org/doi/10.1063/1.1834915 | title= Observation of the lead carbonyls PbnCO (n=1–4): Reactions of lead atoms and small clusters with carbon monoxide in solid argon
|first1=Jiang |last1=Ling |first2=Xu |last2=Qiang |journal=The Journal of Chemical Physics. 122 (3): 034505 |year = 2005|volume = 122|issue = 3|page = 34505|doi=10.1063/1.1834915 |pmid = 15740207|bibcode = 2005JChPh.122c4505J|issn=0021-9606}}</ref> +1,? +3?
| Bi= −3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> −2,? −1,? 0,<ref>Bi(0) state exists in a [[Heterocyclic compound|N-heterocyclic carbene]] complex of dibismuthene; see {{cite journal |first1=Rajesh |last1=Deka |first2=Andreas |last2=Orthaber |title=Carbene chemistry of arsenic, antimony, and bismuth: origin, evolution and future prospects |journal=Royal Society of Chemistry |issue=22 |date=May 9, 2022 |volume=51 |pages=8540–8556 |doi=10.1039/d2dt00755j |pmid=35578901|s2cid=248675805 }}</ref> +1,? +2,? +4,? +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Po= +5<ref name="Thayer p78">{{cite journal |last1=Thayer |first1=John S. |journal=Relativistic Methods for Chemists |title=Relativistic Effects and the Chemistry of the Heavier Main Group Elements |series=Challenges and Advances in Computational Chemistry and Physics |year=2010 |volume=10 |page=78 |doi=10.1007/978-1-4020-9975-5_2|isbn=978-1-4020-9974-8 }}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| At= +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Rn= +2,? +6

| Fr=
| Ra=
| Ac=
| Th=−1,<ref name="Th(-1), U(-1)">Th(-I) and U(-I) have been detected in the gas phase as octacarbonyl anions; see {{cite journal| title=Octacarbonyl Ion Complexes of Actinides [An(CO)8]+/− (An=Th, U) and the Role of f Orbitals in Metal–Ligand Bonding
|first1=Chi |last1=Chaoxian |first2=Pan |last2=Sudip |first3=Jin |last3=Jiaye |first4=Meng |last4=Luyan |first5=Luo |last5=Mingbiao |first6=Zhao |last6=Lili |first7=Zhou |last7=Mingfei |first8=Frenking |last8=Gernot |journal=Chemistry (Weinheim an der Bergstrasse, Germany). 25 (50): 11772–11784 |year = 2019|volume = 25|issue = 50|pages = 11772–11784|doi=10.1002/chem.201902625 |issn=0947-6539 |pmc=6772027
|pmid=31276242}}</ref> +1,? +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +3<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Pa=+2,? +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| U=−1,<ref name="Th(-1), U(-1)">Th(-I) and U(-I) have been detected in the gas phase as octacarbonyl anions; see {{cite journal| title=Octacarbonyl Ion Complexes of Actinides [An(CO)8]+/− (An=Th, U) and the Role of f Orbitals in Metal–Ligand Bonding
|first1=Chi |last1=Chaoxian |first2=Pan |last2=Sudip |first3=Jin |last3=Jiaye |first4=Meng |last4=Luyan |first5=Luo |last5=Mingbiao |first6=Zhao |last6=Lili |first7=Zhou |last7=Mingfei |first8=Frenking |last8=Gernot |journal=Chemistry (Weinheim an der Bergstrasse, Germany). 25 (50): 11772–11784 |year = 2019|volume = 25|issue = 50|pages = 11772–11784|doi=10.1002/chem.201902625 |issn=0947-6539 |pmc=6772027
|pmid=31276242}}</ref> +1,? +2,? +3,<ref>{{cite book|title=The Chemistry of the Actinide and Transactinide Elements|edition=3rd|editor1=Morss, L.R. |editor2=Edelstein, N.M. |editor3=Fuger, J. |place=Netherlands|publisher=Springer|year=2006|isbn=978-9048131464}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Np= +2,? +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name="Dutkiewicz2017">Np(II), (III) and (IV) have been observed, see {{cite journal|doi=10.1039/C7SC00034K|pmid=28553487|pmc=5431675|year=2017|title=Reduction chemistry of neptunium cyclopentadienide complexes: from structure to understanding|first1=Michał S.|last1=Dutkiewicz|first2=Christos|last2=Apostolidis|first3=Olaf|last3=Walter|first4=Polly L|last4=Arnold|volume=8|issue=4|journal=Chem. Sci.|pages=2553–2561}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Pu= +2,? +3,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>, +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +8
| Am= +2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +6,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +7
| Cm= +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5,<ref name="Kovács2018">{{cite journal |last1=Kovács |first1=Attila |last2=Dau |first2=Phuong D. |last3=Marçalo |first3=Joaquim |last4=Gibson |first4=John K. |date=2018 |title=Pentavalent Curium, Berkelium, and Californium in Nitrate Complexes: Extending Actinide Chemistry and Oxidation States |journal=Inorg. Chem. |volume=57 |issue=15 |pages=9453–9467 |publisher=American Chemical Society |doi=10.1021/acs.inorgchem.8b01450 |pmid=30040397 |osti=1631597 |s2cid=51717837 }}</ref> +6<ref name="CmO3">{{cite journal |last1=Domanov |first1=V. P. |last2=Lobanov |first2=Yu. V. |date=October 2011 |title=Formation of volatile curium(VI) trioxide CmO3 |journal=Radiochemistry |volume=53 |issue=5 |pages=453–6 |publisher=SP MAIK Nauka/Interperiodica |doi=10.1134/S1066362211050018|s2cid=98052484 }}</ref>
| Bk=+2,? +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref name="Kovács2018">{{cite journal |last1=Kovács |first1=Attila |last2=Dau |first2=Phuong D. |last3=Marçalo |first3=Joaquim |last4=Gibson |first4=John K. |date=2018 |title=Pentavalent Curium, Berkelium, and Californium in Nitrate Complexes: Extending Actinide Chemistry and Oxidation States |journal=Inorg. Chem. |volume=57 |issue=15 |pages=9453–9467 |publisher=American Chemical Society |doi=10.1021/acs.inorgchem.8b01450 |pmid=30040397 |osti=1631597 |s2cid=51717837 }}</ref>
| Cf=+2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +5<ref>{{Greenwood&Earnshaw2nd|page=1265}}</ref><ref name="Kovács2018">{{cite journal |last1=Kovács |first1=Attila |last2=Dau |first2=Phuong D. |last3=Marçalo |first3=Joaquim |last4=Gibson |first4=John K. |date=2018 |title=Pentavalent Curium, Berkelium, and Californium in Nitrate Complexes: Extending Actinide Chemistry and Oxidation States |journal=Inorg. Chem. |volume=57 |issue=15 |pages=9453–9467 |publisher=American Chemical Society |doi=10.1021/acs.inorgchem.8b01450 |pmid=30040397 |osti=1631597 |s2cid=51717837 }}</ref>
| Es=+2,<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref> +4
| Fm=+2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Md=+2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| No=+2<ref name=GE28>{{Greenwood&Earnshaw2nd|page=28}}</ref>
| Lr=

}}
|predicted={{#switch:{{{symbol|}}}
| Rf=(+3), (+4)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Db= (+3), (+4), (+5)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Sg= (+3), (+4), (+5), (+6)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Bh= (+3), (+4), (+5), (+7)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Hs= (+3), (+4), (+6), (+8)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Mt= (+1), (+3), (+6)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Ds= (+2), (+4), (+6)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Rg= (−1), (+3), (+5)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Cn= (+2), (+4)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>
| Nh=
| Fl=
| Mc=
| Lv= (−2),<ref name="Thayer p83">{{cite journal |last1=Thayer |first1=John S. |journal=Relativistic Methods for Chemists |title=Relativistic Effects and the Chemistry of the Heavier Main Group Elements |series=Challenges and Advances in Computational Chemistry and Physics |year=2010 |volume=10 |page=83 |doi=10.1007/978-1-4020-9975-5_2|isbn=978-1-4020-9974-8 }}</ref> (+4)
| Ts= (−1), (+5)
| Og= (−1),<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref> (+1),<ref name=hydride>{{cite journal|journal=Journal of Chemical Physics |volume=112|issue=6|year=2000|title=Spin–orbit effects on the transactinide p-block element monohydrides MH (M=element 113–118)|first1=Young-Kyu|last1=Han|first2=Cheolbeom |last2=Bae|first3=Sang-Kil |last3=Son|first4=Yoon Sup|last4=Lee|doi=10.1063/1.480842|page=2684|bibcode=2000JChPh.112.2684H}}</ref> (+2),<ref name=Kaldor/> (+4),<ref name=Kaldor>{{cite book|title=Theoretical Chemistry and Physics of Heavy and Superheavy Elements|first1=Uzi |last1=Kaldor |first2=Stephen |last2=Wilson |page=105 |year=2003 |publisher=Springer|isbn=978-1402013713|url=https://books.google.com/books?id=0xcAM5BzS-wC&q=element+118+properties|access-date=2008-01-18}}</ref> (+6)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref>

| Uue= (+1), (+3), (+5)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref><ref name=Cao>{{cite journal |last1=Cao |first1=Chang-Su |last2=Hu |first2=Han-Shi |last3=Schwarz |first3=W. H. Eugen |last4=Li |first4=Jun |date=2022 |title=Periodic Law of Chemistry Overturns for Superheavy Elements |type=preprint |url=https://chemrxiv.org/engage/chemrxiv/article-details/63730be974b7b6d84cfdda35 |journal=[[ChemRxiv]] |volume= |issue= |pages= |doi=10.26434/chemrxiv-2022-l798p |access-date=16 November 2022}}</ref>
| Ubn= (+2),<ref name=Thayer>{{cite journal |last1=Thayer |first1=John S. |journal=Relativistic Methods for Chemists |title=Relativistic Effects and the Chemistry of the Heavier Main Group Elements |series=Challenges and Advances in Computational Chemistry and Physics |year=2010 |volume=10 |page=84 |doi=10.1007/978-1-4020-9975-5_2|isbn=978-1-4020-9974-8 }}</ref> (+4), (+6)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref><ref name=Cao>{{cite journal |last1=Cao |first1=Chang-Su |last2=Hu |first2=Han-Shi |last3=Schwarz |first3=W. H. Eugen |last4=Li |first4=Jun |date=2022 |title=Periodic Law of Chemistry Overturns for Superheavy Elements |type=preprint |url=https://chemrxiv.org/engage/chemrxiv/article-details/63730be974b7b6d84cfdda35 |journal=[[ChemRxiv]] |volume= |issue= |pages= |doi=10.26434/chemrxiv-2022-l798p |access-date=16 November 2022}}</ref>
| Ubu= (+3)<ref name=Haire>{{cite book| title=The Chemistry of the Actinide and Transactinide Elements| editor1-last=Morss| editor2-first=Norman M.| editor2-last=Edelstein| editor3-last=Fuger| editor3-first=Jean| last1=Hoffman| first1=Darleane C.| last2=Lee| first2=Diana M.| last3=Pershina| first3=Valeria| chapter=Transactinides and the future elements| publisher=[[Springer Science+Business Media]]| year=2006| isbn=978-1-4020-3555-5| location=Dordrecht, The Netherlands| edition=3rd| ref=CITEREFHaire2006}}</ref><ref name=Amador>{{cite journal |last1=Amador |first1=Davi H. T. |last2=de Oliveira |first2=Heibbe C. B. |first3=Julio R. |last3=Sambrano |first4=Ricardo |last4=Gargano |first5=Luiz Guilherme M. |last5=de Macedo |date=12 September 2016 |title=4-Component correlated all-electron study on Eka-actinium Fluoride (E121F) including Gaunt interaction: Accurate analytical form, bonding and influence on rovibrational spectra |journal=Chemical Physics Letters |volume=662 |pages=169–175 |doi=10.1016/j.cplett.2016.09.025|bibcode=2016CPL...662..169A |hdl=11449/168956 }}</ref>
| Ubb= (+4)<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172, based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Ubt=
| Ubq= (+6)<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172, based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Ubp=(+6), (+7)<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172, based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Ubh=(+4), (+6), (+8)<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172, based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Ubo=(){{Infobox element/symbol-to-oxidation-state/comment|comment=predicted|engvar={{{engvar|}}}}}<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172, based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Ube=(), (){{Infobox element/symbol-to-oxidation-state/comment|comment=predicted|engvar={{{engvar|}}}}}<ref name="Pyykkö2011">{{Cite journal|last1=Pyykkö|first1=Pekka|author-link=Pekka Pyykkö|title=A suggested periodic table up to Z ≤ 172,? based on Dirac–Fock calculations on atoms and ions|journal=Physical Chemistry Chemical Physics|volume=13|issue=1|pages=161–8|year=2011|pmid=20967377|doi=10.1039/c0cp01575j|bibcode = 2011PCCP...13..161P }}</ref>
| Uts=


}}
}}<noinclude>
{{documentation}}
</noinclude>

Yongchulu station

2024-12-02T15:50:22Z

Leiem: etymology

{{Short description|Metro station in Nanjing, China}}
{{Infobox station
| name = Yongchulu
| native_name = 永初路
| native_name_lang = zh-Hans
| symbol_location = nanjing
| symbol = metro
| image = 20210529_永初路站_大字壁.jpg
| address = [[Jianye District]], [[Nanjing]], [[Jiangsu]]
| country = China
| coordinates =
| operator = Nanjing Metro Co. Ltd.
| line = {{rail color box|system=NJM|line=7|inline=yes}} {{rail color box|system=NJM|line=S3|inline=yes}}
| structure = Underground
| opened = 6 December 2017
| services = {{Adjacent stations|system=NJM|line1=7|left1=Jialingjiangdongjie|right1=Taiqinglu|line2=S3|left2=Youfangqiao|right2=Pingliangdajie}}
}}

'''Yongchulu station''' ({{zh|s=永初路站}}), is a [[metro station|station]] of [[Line S3, Nanjing Metro|Line S3]] of the [[Nanjing Metro]]. It started operations on 6 December 2017.<ref>{{cite web|url=http://www.njmetro.com.cn/service_04_new.aspx?LineNum=9|title=S3号线|publisher=Nanjing Metro |access-date=30 December 2017}}</ref> On 28 December 2023, with the opening of the southern part of Line 7, it became an interchange station between Line 7 and Line 10.<ref>{{Cite web|url=https://mp.weixin.qq.com/s?__biz=MjM5NTU2MzY5Mg==&mid=2651438950&idx=1&sn=ede733d22e05aabaa3ef49ed9f0f17bb|script-title=zh:7号线南段明天上午9时开通初期运营|trans-title=The Southern part of Nanjing Metro will be open at 9 o'clock tomorrow|language=zh|work=Nanjing Metro|date=December 27, 2023|access-date=December 27, 2023}}</ref> The station name is derived from the era name "Yongchu" of [[Emperor Wu of Song|Emperor Wu of the Song Dynasty]].<ref>{{cite web|author=Feng, Yuanfang|script-title=zh:透过地铁站名，理解何以南京|publisher=Xinhua Daily|doi=10.28872/n.cnki.nxhrb.2024.007680|url=https://www.chndoi.org/Resolution/Handler?doi=10.28872/n.cnki.nxhrb.2024.007680}}</ref>

==References==
{{reflist}}

{{Nanjing Metro/stations
|lineS3=yes
}}

{{coord missing|Jiangsu}}

[[Category:Railway stations in China opened in 2017]]
[[Category:Nanjing Metro stations]]

Cobalt(II) phosphide

2024-12-02T07:09:43Z

Leiem: correct the CAS RN

{{Chembox
| ImageFile =
| ImageSize =
| IUPACName = Cobalt(II) phosphide
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 129097-04-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 166621
| RTECS =
| EINECS = 235-212-4
| ChemSpiderID = 145804
| SMILES = [P-3].[P-3].[Co+2].[Co+2].[Co+2]
| StdInChI = 1S/3Co.2P/q3*+2;2*-3
| StdInChIKey = YYHKCTWKZVGLSL-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = Co3P2
| MolarMass = 238.747 g/mol

| SolubleOther =
| RefractIndex =
}}
|Section3={{Chembox Structure
| CrystalStruct =
}}
|Section4={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Cobalt(II) phosphide''' is an [[inorganic compound]] with the [[chemical formula]] Co3P2.<ref>[http://ull.chemistry.uakron.edu/erd/Chemicals/26000/24572.html University of Akron Chemical Database] {{webarchive|url=https://archive.today/20121210114316/http://ull.chemistry.uakron.edu/erd/Chemicals/26000/24572.html |date=2012-12-10 }}</ref>

==References==
{{reflist}}

{{Cobalt compounds}}
{{Phosphides}}
[[Category:Cobalt(II) compounds]]
[[Category:Phosphides]]

{{Inorganic-compound-stub}}

Uranium ruthenium silicide

2024-11-29T08:06:16Z

Leiem: Chembox

{{refimprove|date=May 2016}}
{{Chembox
| Name =
| ImageFile = Crystal_structure_of_URu2Si2.jpg
| ImageSize = 160px
| ImageAlt =
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 87588-60-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 
}}
| Section2 = {{Chembox Properties
|U=1|Ru=2|Si=2
}}
}}
'''Uranium ruthenium silicide''' ('''URu2Si2''') is a [[heavy fermion]] alloy composed of [[uranium]], [[ruthenium]], and [[silicon]]. URu2Si2 has the same '122' tetragonal crystal structure as [[122 iron arsenide|many other compounds]] of present condensed matter research. URu2Si2 is a [[superconductor]] with a [[hastatic order]] (HO) phase below a temperature of 17.5 [[Kelvin|K]].<ref>{{cite journal |author=H.-H. Kung1 |author2=R. E. Baumbach |author3=E. D. Bauer |author4=V. K. Thorsmølle |author5=W.-L. Zhang |author6=K. Haule |author7=J. A. Mydosh |author8=G. Blumberg |title=Chirality density wave of the "hidden order" phase in URu2Si2 |journal=Science |date=20 March 2015 |volume=347 | issue=6228 | pages=1339–1342 |doi=10.1126/science.1259729 |pmid=25678557 |arxiv=1410.6398 |bibcode=2015Sci...347.1339K |s2cid=30976070 }}</ref><ref>{{cite journal |author=Premala Chandra |author2=Piers Coleman |author3=Rebecca Flint |title=Hastatic order in the heavy-fermion compound URu2Si2 |journal=Nature |date=31 January 2013 |volume=493 |issue=7434 | pages=621–626 |doi=10.1038/nature11820 |pmid=23364741 |arxiv=1207.4828 |bibcode=2013Natur.493..621C |s2cid=205232317 }}</ref> Below this temperature, it is magnetic, and below about 1.5 K it superconducts.<ref>{{cite book|first=Gernot | last=Goll |title=Unconventional Superconductors: Experimental Investigation of the Order-Parameter Symmetry | pages=107–111 |publisher=Springer| year=2006 |isbn=978-3-540-28985-2 |url=https://books.google.com/books?id=ISvIgVbxIs4C&pg=PA107}}</ref> However, the nature of the ordered phase below 17.5K is still under debate despite a wide variety of scenarios that have been proposed to explain this phase.

== References==
{{Reflist}}
{{uranium compounds}}
{{ruthenium compounds}}

[[Category:Correlated electrons]]
[[Category:Superconductivity]]
[[Category:Silicides]]
[[Category:Uranium compounds]]
[[Category:Ruthenium compounds]]

{{Inorganic-compound-stub}}

Deekonda2016

2024-11-29T06:48:20Z

Leiem: CAS RN

{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| drug_name = Deekonda2016
| type =
| IUPAC_name = <nowiki>N-[[1-[[(5S)-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]piperidin-2-yl]methyl]-N-phenylpropanamide</nowiki>
| image = Deekonda2016_structure.png
| width = 200

| alt =
| caption =
| tradename =
| MedlinePlus =
| licence_EU =
| licence_US =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA = 
| legal_DE = 
| legal_NZ = 
| legal_UK = 
| legal_US =
| legal_EU =
| legal_UN = 
| routes_of_administration =
| addiction_liability = 
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = 
| CAS_number_Ref = {{Cascite|correct|CAS}}
| CAS_number = 1849034-34-9
| ChEMBL =
| ATC_prefix =
| ATC_suffix =
| PubChem = 127037397
| DrugBank =
| KEGG =
| ChemSpiderID =
| UNII = 
| C = 26
| H = 34
| N = 2
| O = 2
| melting_point =
| smiles = CCC(=O)N(CC1CCCCN1CC2=CC3=C(C=C2)[C@H](CCC3)O)C4=CC=CC=C4
| StdInChI = 1S/C26H34N2O2/c1-2-26(30)28(22-10-4-3-5-11-22)19-23-12-6-7-16-27(23)18-20-14-15-24-21(17-20)9-8-13-25(24)29/h3-5,10-11,14-15,17,23,25,29H,2,6-9,12-13,16,18-19H2,1H3/t23?,25-/m0/s1
| StdInChIKey = MSWKQEUSFJHFAI-YNMFNDETSA-N
}}

'''Deekonda2016''' is a [[piperidine]]-based [[opioid]] [[analgesic]] compound, developed through modification of the [[fentanyl]] scaffold and with similar potency to fentanyl. It was designed as a mixed μ/δ opioid agonist but is much more selective for the [[μ-opioid receptor]], with a binding affinity of 4 nM.<ref>{{cite journal | vauthors = Deekonda S, Wugalter L, Kulkarni V, Rankin D, Largent-Milnes TM, Davis P, Bassirirad NM, Lai J, Vanderah TW, Porreca F, Hruby VJ | title = Discovery of 5-substituted tetrahydronaphthalen-2yl-methyl with N-phenyl-N-(piperidin-4-yl)propionamide derivatives as potent opioid receptor ligands | journal = Bioorganic & Medicinal Chemistry | volume = 23 | issue = 18 | pages = 6185–6194 | date = September 2015 | doi = 10.1016/j.bmc.2015.07.071 | pmid = 26299827 | pmc = 4642887 }}</ref><ref>{{cite journal | vauthors = Deekonda S, Rankin D, Davis P, Lai J, Vanderah TW, Porecca F, Hruby VJ | title = Design synthesis and structure-activity relationship of 5-substituted (tetrahydronaphthalen-2yl)methyl with N-phenyl-N-(piperidin-2-yl)propionamide derivatives as opioid ligands | journal = Bioorganic & Medicinal Chemistry | volume = 24 | issue = 2 | pages = 85–91 | date = January 2016 | doi = 10.1016/j.bmc.2015.11.030 | pmid = 26712115 | pmc = 4873254 }}</ref><ref>{{cite journal | vauthors = Lipiński PF, Kosson P, Matalińska J, Roszkowski P, Czarnocki Z, Jarończyk M, Misicka A, Dobrowolski JC, Sadlej J | title = Fentanyl Family at the Mu-Opioid Receptor: Uniform Assessment of Binding and Computational Analysis | journal = Molecules | volume = 24 | issue = 4 | date = February 2019 | page = 740 | doi = 10.3390/molecules24040740 | doi-access = free | pmid = 30791394 | pmc = 6412969 }}</ref><ref>{{cite journal | vauthors = Wu Z, Hruby VJ | title = Toward a Universal μ-Agonist Template for Template-Based Alignment Modeling of Opioid Ligands | journal = ACS Omega | volume = 4 | issue = 17 | pages = 17457–17476 | date = October 2019 | doi = 10.1021/acsomega.9b02244 | pmid = 31656918 | pmc = 6812133 }}</ref>

== See also ==
* [[Brorphine]]
* [[Fentanyl tropane]]
* [[Phenampromide]]
* [[R6890]]
* [[Secofentanyl]]
* [[List of fentanyl analogues]]

== References ==
{{reflist}}

{{Opioids}}

[[Category:Designer drugs]]
[[Category:Opioids]]

Wikipedia:Reference desk/Science

2024-11-28T04:24:33Z

Leiem: /* Are there any volatile gold compounds? */

<noinclude>{{Wikipedia:Reference desk/header|WP:RD/S}}
[[Category:Non-talk pages that are automatically signed]]
[[Category:Pages automatically checked for incorrect links]]
[[Category:Wikipedia resources for researchers]]
[[Category:Wikipedia help forums]]
[[Category:Wikipedia reference desk|Science]]
[[Category:Wikipedia help pages with dated sections]] </noinclude>

= November 14 =

== Tau propagation ==

Create redirect [[Tau propagation]] to <s>[[Tau_protein#Tau hypothesis of Alzheimer's disease]]</s> which section of [[Tau protein]]? [[User:ExclusiveEditor|ExclusiveEditor]] [[User talk:ExclusiveEditor|Notify Me!]] 20:12, 14 November 2024 (UTC)

:It is a controversial hypothesis that cannot be dealt with with a simple redirect.  --[[User talk:Lambiam#top|Lambiam]] 05:38, 15 November 2024 (UTC)

= November 15 =

== Why are [[Koala]]s vulnerable to extinction ==

Hi. I was wondering why Koalas are vulnerable to extinction unlike Kangaroos, which are way more common, and both animals are found in Australia. Please let me know. Thanks. [[Special:Contributions/2605:B100:142:A3B7:1D63:4EBE:694C:7BCA|2605:B100:142:A3B7:1D63:4EBE:694C:7BCA]] ([[User talk:2605:B100:142:A3B7:1D63:4EBE:694C:7BCA|talk]]) 04:22, 15 November 2024 (UTC)
:The article has some information on it. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 04:54, 15 November 2024 (UTC)
:Habitat loss, especially lack of connected habitats, chlamidia, overcrowding, dogs. I doubt they are anywhere near extinct. [[User:Greglocock|Greglocock]] ([[User talk:Greglocock|talk]]) 05:17, 15 November 2024 (UTC)
::It might have been quicker to Google your question - this was one of the first results; [https://www.savethekoala.com/about-koalas/threats-to-the-koala/ ''Threats To The Koala'']. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 11:44, 15 November 2024 (UTC)
:Kangaroos are more flexible in what they eat, and can move large distances faster. But koalas are cuter and so have more public awareness and are used as the poster animal, like [[giant panda]]s. [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 23:52, 15 November 2024 (UTC)
:More generally, the more specialised an organism is, the less likely it is to go extinct as a result of competition from other species but the more likely it is to be affected by environmental changes. So Koalas aren't going to have to worry about some other similar animal taking over its territory and taking all the eucalyptus for themselves. But they would be vulnerable to anything that killed off the eucalyptus. [[User:Wardog|Iapetus]] ([[User talk:Wardog|talk]]) 12:42, 19 November 2024 (UTC)

== Admiral Nakhimov ==

In the time leading up to [[SS Admiral Nakhimov#Sinking|the shipwreck in late August 1986]], is it known whether Captain Victor Tkachenko of the ''Petr Vasev'' had been transferred there from a smaller ship? Because I've read an article a while ago in [[Science et Vie]] (the [[Nauka i Zhizn|Russian version]]) about the human factors in that disaster, and this would be the only conclusion which would make any sense! [[Special:Contributions/2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6|2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6]] ([[User talk:2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6|talk]]) 14:50, 15 November 2024 (UTC)

:I think the question is better suited at [[WP:RDH]]. [[User:ExclusiveEditor|ExclusiveEditor]] [[User talk:ExclusiveEditor|Notify Me!]] 20:56, 16 November 2024 (UTC)

== Why don't plants photosynthesize efficiently? ==

[[Photosynthesis]] is 6% efficient in green plants, 20% in solar panels. I see hints that it's more efficient in [[red algae]], but I can't find a figure. They need to be efficient because they live in low light environments. There's a note here at [[Artificial_photosynthesis#Some_advantages,_disadvantages,_and_efficiency]] which says photosynthesis is typically 1% efficient! What's up with that? Something about not having enough CO2 around in the air to have any use for the energy? I found [https://www.quantamagazine.org/why-are-plants-green-to-reduce-the-noise-in-photosynthesis-20200730/ this article] which says {{tq|For the cell, a steady input of electrical energy coupled to a steady output of chemical energy is best: Too few electrons reaching the reaction center can cause an energy failure, while “too much energy will cause free radicals and all sorts of overcharging effects” that damage tissues}}, but that seems to boil down to "the cells can't do it". [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 20:54, 15 November 2024 (UTC)
:Evolution doesn't necessarily aim for perfection, just for survival. If that 6 percent is good enough for survival, there would likely be no evolutionary pressure to do it "better". ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 22:55, 15 November 2024 (UTC)
::Trees compete for light, so there's some pressure to grow faster, isn't there? [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 23:15, 15 November 2024 (UTC)
:If you want to compare solar panel effiency, you should compare production of a chemical like glucose from carbon dioxide using electricity. Or should we allow any other reduced and useful carbon compound. As plants do not just produce electricity. [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 23:23, 15 November 2024 (UTC)
:Photosynthesis in plants can be very efficient under the right conditions. For instance, from photon to hydrogen/ATP it is nearly 100%,because the difference to really 100% is what destroys the chlorophyll. And replacing destroyed chlorophyll is costly, energywise and sometimes it even costs magnesium. Therefore that part is developed to maximize efficiency. Another goal is in the development of the carbon dioxide capture. For this one must know that chemical reactions with gases are very dependent on the pressure of the gases. Even the direction, that is if it's exothermic or endothermic, depends highly on the pressure. If RuBisCo would be faster the carbon dioxide could not come fast enough onto the site of enzymatic activity and would therefore drop in pressure there. Which in turn would drive the demand for energy up in this pathway. To overcome the RuBisCo-limit the C4 plants were developed. But they have other deficiencies, where they additionally spend energy to capture carbon dioxide for storage, and don't get it back at the RuBisCo.
:Generally plants have too much energy for the amount of water and, most important, carbon dioxide, to synthesize sugar. Some hydrogen has to be dumped into the production of [[Ethen]] and [[Latex]] or other hydrocarbons. Of course, the energy for this is typically not counted towards the efficiency of photosynthesis. Moreover some ATP is simply hydrolysed for heating. Or for regeneration of ADP. Whichever is needed where this takes place.
:For comparison there exist bacteria where chemical reactions are driven by 1/16th of a proton, that is 1/64 ATP-Unit. That only works with a large [[Quantum state]] in a superposition. If someone would want to maximise the efficiency of the photosynthesis, the recipe is there for the taking. But think of the side effects! [[Special:Contributions/176.2.78.14|176.2.78.14]] ([[User talk:176.2.78.14|talk]]) 06:02, 16 November 2024 (UTC)
::: For this one must know that chemical reactions with gases are very dependent on the pressure of the gases. Even the direction, that is if it's exothermic or endothermic, depends highly on the pressure. If RuBisCo would be faster the carbon dioxide could not come fast enough onto the site of enzymatic activity and would therefore drop in pressure there.
::Does this mean that plants photosynthesize more efficiently in environments with elevated air pressure? Can you recommend any resources for learning more about that? Thank you! -- [[User:Avocado|Avocado]] ([[User talk:Avocado|talk]]) 14:21, 16 November 2024 (UTC)
:::@[[User:Avocado|Avocado]] Not air pressure but partial pressure of carbon dioxide. That's standard in greenhouses. See [[Greenhouse#Carbon dioxide enrichment]] for details. [[User:Michael D. Turnbull|Mike Turnbull]] ([[User talk:Michael D. Turnbull|talk]]) 12:57, 20 November 2024 (UTC)
::::Thank you! Is there any research about elevated air pressure, too? IIRC, humans absorb oxygen more efficiently at higher air pressures (up to a point), so it seems like it might make sense (based on both that and what little I know about gas exchange across membranes) for plants to absorb CO2 better at higher air pressures as well. -- [[User:Avocado|Avocado]] ([[User talk:Avocado|talk]]) 21:02, 20 November 2024 (UTC)
:::::humans are developed to an oxygen pressure of 0,22 atm. Over it there are many reactions that disturb the physiology, under it there is to over 0,17 atm no difference as long as no (not the least amount) [[Carbon monoxide]] comes into play. But even 0,11 atm is sufficient for up to 2 hours. At this low pressure of oxygen no normal combustion is possible but nobody needs an oxygen mask immediately. In case of a fire that is a great advantage for fire fighting. [[Special:Contributions/176.3.66.65|176.3.66.65]] ([[User talk:176.3.66.65|talk]]) 23:04, 22 November 2024 (UTC)
=== What about near volcanos? ===
Are there specialized plants growing in carbon dioxide rich environments that photosynthesize faster? [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 12:42, 16 November 2024 (UTC)
:No. I heard there are only a few places where there is consistent outgassing of CO2 and yes, plants grow faster there. The thing is, plants are so starved for CO2 that increasing CO2 concentration instantaneously leads to increased sugar production. We think that the current photosynthesis evolved in a time when the atmosphere was like Venus's with perhaps 100 times the partial pressure of CO2. Even now, you can put a houseplant in a pure CO2 atmosphere in a glass vessel, and it does great. Another way of putting this is that there can be no natural selection for specialization in growing in a "carbon dioxide rich environment" since that would entail getting ''worse'' at using CO2. [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 21:07, 16 November 2024 (UTC)

== Thermometer thermal mass ==

I'd like to measure the air temperature in a room, outdoors, etc. Ideally by bringing the thermometer, turning it on if it is electronic, and looking at it. All thermometers that I've tried take several minutes to settle, which is annoyingly long. Is that inherent? Are there quicker ones? Don't want to spend a fortune, but "premium" is ok. Thanks. [[Special:Contributions/2601:644:8581:75B0:0:0:0:2CDE|2601:644:8581:75B0:0:0:0:2CDE]] ([[User talk:2601:644:8581:75B0:0:0:0:2CDE|talk]]) 22:12, 15 November 2024 (UTC)
:For an expensive high-tech solution use [[tunable diode laser absorption spectroscopy]] which should measure the temperature in the gas, rather than waiting for it to conduct into a detector. see https://www.yokogawa.com/solutions/products-and-services/measurement/analyzers/gas-analyzers/tunable-diode-laser-spectrometer/#Overview for a product. [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 23:45, 15 November 2024 (UTC)
::a really cheap way to go at it would be [[Resistance thermometer#Coiled elements|Resistance thermometer]] of course in [[Resistance thermometer#Four-wire configuration|Four-wire configuration]]. If the coil is very short, which is possible in four wires, then it will get the temperature in under a second. [[Special:Contributions/176.2.78.14|176.2.78.14]] ([[User talk:176.2.78.14|talk]]) 01:36, 16 November 2024 (UTC)
::Thanks both, the resistance thermometer approach sounds promising. The tunable laser page says "request a quote" which means "too expensive for me to think about". [[Special:Contributions/2601:644:8581:75B0:0:0:0:2CDE|2601:644:8581:75B0:0:0:0:2CDE]] ([[User talk:2601:644:8581:75B0:0:0:0:2CDE|talk]]) 02:45, 16 November 2024 (UTC)
:An [[infrared thermometer]] retails at around USD 10, and reacts in less than a second from when you press the button. It doesn't measure air temperature but if you can assume your walls/floors/furniture/etc are about the same temp, it'll work. [[Special:Contributions/85.76.117.61|85.76.117.61]] ([[User talk:85.76.117.61|talk]]) 15:45, 16 November 2024 (UTC)
::I have one but it is not very consistent between surfaces, and the air temperature can change faster than the furniture temperature. I guess it is better than nothing. Thanks. [[Special:Contributions/2601:644:8581:75B0:0:0:0:2CDE|2601:644:8581:75B0:0:0:0:2CDE]] ([[User talk:2601:644:8581:75B0:0:0:0:2CDE|talk]]) 02:13, 17 November 2024 (UTC)

= November 17 =

== A [[lead zeppelin]] is your [[stairway to heaven]]? ==

In terms of fatalities per [[passenger-mile]], and excluding combat losses during [[World War 1]] (but including accidental losses during the same time period), which [[airships]] were more dangerous to fly in, those filled with [[hydrogen]] or with [[helium]]? I'm aware of the argument that helium-filled airships have a narrower [[flight envelope]], which causes them [[USS Shenandoah|to crash]] [[USS Akron|more often]] -- but, on the other hand, the flammability of hydrogen often had the effect of turning an otherwise survivable crash into [[R-101|one which is fatal for everyone on board]], and also created the danger of [[Dixmude (airship)|explosion from lightning strike]] -- so between these two dangers, which one was the greatest? [[Special:Contributions/2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6|2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6]] ([[User talk:2601:646:8082:BA0:CD5E:73B7:6DF6:2CF6|talk]]) 03:41, 17 November 2024 (UTC)

:Is there a source for the claimed explosion? It is not plausible, scientifically.  --[[User talk:Lambiam#top|Lambiam]] 08:48, 17 November 2024 (UTC)
::In what way not plausible? If your objection is to do with needing oxygen, that airship probably leaked: six months previously, "many small tears appeared". [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 09:39, 17 November 2024 (UTC)
:::It would leak hydrogen out, not oxygen in.  --[[User talk:Lambiam#top|Lambiam]] 10:16, 17 November 2024 (UTC)
::::So if a leak of hydrogen into air is hit by lightning, on top of a balloon made from sausage skin that's filled with more hydrogen, how do you imagine events would unfold after that? [[Hindenburg_disaster#Lightning_hypothesis]] says that ''airship fires have been observed'' under these kind of circumstances. I'm surprised that they were only fires, it makes the outcome sound mild, like lighting a gas stove. [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 10:52, 17 November 2024 (UTC)
:::::If there's a leak in the gas bags, it's plausible you may get an explosive mixture in the space between the gas bags and the outer hull. What exactly happened to Dixmude may never be known, but whether it was an explosion or rapid burning, too rapid for an orderly emergency landing (Hindenburg burned all its lifting gas in about half a minute), doesn't matter; all on board would be dead anyway. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 14:00, 17 November 2024 (UTC)
::::::That would indeed explain it. Without prior mixing with oxygen-containing air, hydrogen burns fiercely in a rapidly advancing front, as seen in the Hindenburg disaster, but not so rapid that there is an explosion.  --[[User talk:Lambiam#top|Lambiam]] 16:46, 17 November 2024 (UTC)
::I found [https://books.google.com/books?id=HHw6AQAAIAAJ&dq=%22the+Dixmude+had+exploded+with+great+violence%22&hl=en a source], but no explanation.  --[[User talk:Lambiam#top|Lambiam]] 10:30, 17 November 2024 (UTC)
:::According to the footnote in [https://www.theguardian.com/theguardian/2010/dec/29/archive-dixmude-airship-disaster-1923 this] republished 1923 article, there was an inquiry in January 1924, so maybe there is a report out there somewhere. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 10:38, 17 November 2024 (UTC)
:This is hard to say...
:A helium-filled airship has less lift for the same volume, so it has to compensate somehow: fewer passengers and passenger-kilometres, giving more accidents per passenger-kilometre, or lighter skin, frame or engines or less fuel, all increasing accident rate.
:A helium-filled airship is less likely to burn. The hydrogen fire itself isn't very lethal (except for those sitting high up in the envelope), but it can accelerate the destruction of the airship, leading to a faster crash, and set the skin and fuel on fire, leaving burning wreckage, which can kill passengers.
:A third effect, which you didn't mention, is the [[heat capacity ratio]]. Helium has a heat capacity ratio of 1.66, hydrogen of 1.41, just like dry air, and moist air has an even lower heat capacity ratio. This means that on descent, helium heats up by [[adiabatic compression]] faster than hydrogen or the surrounding air, increasing the stability of the airship. When flying in slightly superadiabatic dry air, a hydrogen-filled airship is unstable in altitude. If it descends, the lifting gas heats up slower than the surrounding air, decreasing lift and accelerating the descent. This is no problem for helium-filled airships. Those have difficulty changing altitude faster than the time needed to equalise inside and outside temperature.
:When looking at fatalities per passenger-kilometre, it's best to look only at passenger flights. Including military flights, test flights and accidents on the ground will increase the number of accidents without adding passenger-kilometres, making the airship appear more dangerous. Worse, those were the most dangerous occasions for airships. Ground accidents happened when the airship was grounded for bad weather, test flights were obviously more dangerous than regular flights and even when excluding combat damage, military flights were more dangerous as the airship was flown in weather and through manoeuvres that no captain would attempt on a civilian flight. However, excluding all military flights will exclude all helium-filled rigid airships, so no useful statistics are left. The safety record of those four helium-filled rigid airships of the US Navy doesn't appear too good though: three fatal crashes in only a third of the flight hours of Graf Zeppelin. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 16:50, 17 November 2024 (UTC)

:As noted in [[List of airship accidents]], there is a variety of causes, a number of them being weather-related. The most successful airship was the [[LZ 127 Graf Zeppelin|Graf Zeppelin]], which was filled with hydrogen, but never burned up or crashed. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 20:55, 17 November 2024 (UTC)

::There were no helium-filled passenger airships - they were all operated for naval reconnaisance. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 15:56, 19 November 2024 (UTC)
:::There are some modern helium-filled non-rigid or semi-rigid passenger airships, used for sightseeing, but there are no hydrogen-filled modern airships, so there's no useful comparison possible. There are both helium-filled and hydrogen-filled gas balloons, but that isn't really the same thing. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 09:57, 21 November 2024 (UTC)

== Land surveying ==

Does modern land surveying (such as placement of streets after another, width of roads and blocks etc.) in take place using metric units in countries such as Canada, Australia and New Zealand, which have used metric distances for many decades now? Is there any English-speaking country that had already metricated when first surveys for 19th-century cities were done? Are there any downtown grids in English-speaking areas where streets are placed exactly 100 metres apart, and there are ten streets per one kilometre? In grids that place 16 streets per mile, the number of metres passed eventually deviates from number of 100 metres (hectometres) passed, since one mile is not exactly 1,600 metres. Placing ten streets per mile indicates number of miles passed by fourth-to last digit of house numbers, but does not indicate number of feet (or any other imperial unit) passed by whole number. By contrast, placing ten streets per kilometre indicates both number of kilometres passed by fourt-to last digit of house numbers and number of metres passed by whole house numbers. This placing is common in Argentina, but does it occur in any English-speaking country? --[[User:40bus|40bus]] ([[User talk:40bus|talk]]) 16:01, 17 November 2024 (UTC)
:There are 100 meter blocks in Melbourne, Australia if I remember correctly. Mile/km/block-based addresses is not the original England way which was to count plots or buildings and call an unexpected new building in between the address of its neighbor suffixed with a letter or fraction. Manhattan's a hybrid: 1 address pair per 20ft plot of ownable (non-street) distance except 1 axis is 100 per block causing gaps like 153, 155, 201 except 3LPM5's 100 per 2 blocks cause Lex+Mad are new. [[User:Sagittarian Milky Way|Sagittarian Milky Way]] ([[User talk:Sagittarian Milky Way|talk]]) 05:48, 18 November 2024 (UTC)
::The Melbourne blocks are 200 metres and then only by a coincidence; they are actually 10 [[Chain (unit)|chain]]s or 660 feet, which happily converts to 201.17 metres. See [[Hoddle Grid]] for the details. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 15:38, 19 November 2024 (UTC)
:::This is a new South Australian development near to where I live and the blocks are measured in metres, but not in nice whole metres. Zoom in and move the map to see details of the blocks. https://villawoodproperties.com.au/community/oakden-rise/find-buy/interactive-masterplan/ [[User:TrogWoolley|TrogWoolley]] ([[User talk:TrogWoolley|talk]]) 09:41, 18 November 2024 (UTC)
:::The same inaccuracy as 16 per mile then. [[User:Sagittarian Milky Way|Sagittarian Milky Way]] ([[User talk:Sagittarian Milky Way|talk]]) 01:29, 20 November 2024 (UTC)

:Just to note that Australia, South Africa, New Zealand and Canada all began [[metrication]] in the 1960s or very early 1970s, so using metric measurements for any official purposes in the 19th-century would be highly improbable. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 15:54, 19 November 2024 (UTC)
::Is the any English-speaking country that already used metric measurement for official purposes in the 19th century? Was there anything that was measured in metric during [[Victorian times]] in the UK? --[[User:40bus|40bus]] ([[User talk:40bus|talk]]) 21:20, 19 November 2024 (UTC)
:::There was apparently a 6 mm government cartridge specification, the [[6mm Lee Navy]]. I haven't dug up a contemporary source using mm, but it looks like it was so named even in 1895. (Note though the alternate .236 name.) [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 06:26, 20 November 2024 (UTC)
:::::[https://books.google.co.uk/books?id=oR9BAQAAMAAJ&pg=PA480 ''The Abridgment: Containing Messages of the President of the United States to the Two Houses of Congress'' (1898) p. 480]:
:::::{{xt|"Ten thousand 6 mm. Lee straight pull rifles have been supplied..."}} [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 12:44, 20 November 2024 (UTC)
::::On the subject of weapons, the [[QF 2-pounder naval gun]] of 1915 was made by the very British firm of [[Vickers]] and had a calibre of exactly 40 mm, but was known in British service by the weight of its shell in Imperial measure. The use of metric units here may be connected with the acquisition by Vickers of the [[Maxim Nordenfelt Guns and Ammunition Company]] in 1897, which although a British company, had its origin in the company owned by [[Thorsten Nordenfelt]], a Swedish inventor. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 12:33, 20 November 2024 (UTC)
::A near miss though. Québec was a French colony using French units until 1763, switched to Imperial units after that, which was only 32 years before France metricated.
::South Africa is an even nearer miss. It (or at least, the Cape Colony) was a Dutch colony until 1795, which is the year when the Netherlands metricated. The British then introduced Imperial units as they took over. Dutch rule was briefly restored in 1803–1806, but it appears this was too short to make the switch to metric. The Boers went their own way, continuing the use of traditional Dutch units (no longer used in the Netherlands) until Imperial units were made the standard in 1922: one of the last countries to switch to Imperial units. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 19:31, 19 November 2024 (UTC)

== How sampling rate in ADC adjusted or set ? ==

I am interested to learn how sampling rate in [[Analog-to-digital converter]] adjusted or set ?
This page: [[Sampling (signal processing)]] didn't explain how it was adjusted. [[User:HarryOrange|HarryOrange]] ([[User talk:HarryOrange|talk]]) 18:36, 17 November 2024 (UTC)
:Do you mean on a black box ADC (the sort of thing you have in a lab), or do you mean on an adc chip? [[User:Greglocock|Greglocock]] ([[User talk:Greglocock|talk]]) 22:00, 17 November 2024 (UTC)
::@[[User:Greglocock|Greglocock]] I mean any typical ADC chip. How Sampling rate is adjusted? [[User:HarryOrange|HarryOrange]] ([[User talk:HarryOrange|talk]]) 05:03, 18 November 2024 (UTC)
::I guess you read the data sheet for the chip. eg p41 and 42 here https://www.analog.com/media/en/technical-documentation/data-sheets/ad7768-7768-4.pdf [[User:Greglocock|Greglocock]] ([[User talk:Greglocock|talk]]) 06:04, 18 November 2024 (UTC)
:::An ADC sampling rate is determined by the data rate of the desired digital audio format. [[Sampling (signal processing)|This article]] gives many examples of which 44.1 kHz, 48 kHz, 88.2 kHz and 96 kHz are typical. A designer simply ensures that an ADC chip receives a digital clock signal at appropriate frequency. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 20:17, 19 November 2024 (UTC)
::::Which is almost irrelevant to the question. An ADC chip or lab instrument can sample at many different rates. [[User:Greglocock|Greglocock]] ([[User talk:Greglocock|talk]]) 21:55, 19 November 2024 (UTC)

= November 18 =

== Open-air dust explosions ==

[[Dust explosion#Conditions required]] says {{tq|There are five necessary conditions for a dust explosion}}. It even has a pointless diagram that arranges the five conditions in a pentagon with "dust explosion" in the middle. Condition 5 is confinement. But further down the page, [[Dust_explosion#Mechanism]] has a series of photographs demonstrating a dust explosion in open air. And [[thermobaric weapons]], although more effective at killing people in confined spaces, seem to explode just fine in the open. So is condition 5, as a "necessary condition", plain wrong, perhaps an exaggeration of the fact that confinement makes a dust explosion more likely?

Supplementary question: I hear residents of Lahore and Delhi are wondering if their very sooty smog might one day explode. Is this at all plausible? [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 00:09, 18 November 2024 (UTC)

::{{small|Pointless? It is a five-pointed diagram.  --[[User talk:Lambiam#top|Lambiam]] 06:53, 18 November 2024 (UTC)}}
:In general, not only for dust, for [[detonation]] to occur, a mix of fuel and oxygen within the [[explosive limits]] has to be present in a compact largish volume. Upon detonation, the pressure in this volume will rapidly increase tremendously within (typically) microseconds. If the volume is not confined by an enclosure, the gases resulting from the combustion will expand supersonically with a shock wave that may or may not cause damage, depending on the power released and the environment. If the volume is confined by an enclosure, the enclosure may be able to withstand the pressure and contain the gases – possibly with controlled release through [[safety valve]]s. (See e.g. [[Pyréolophore]].) Otherwise, if the enclosure is broached, the gases will also expand explosively.
:The OSHA fact sheet that is the source of our five-pointed list of conditions is actually about another scenario. It considers the case in which ignition merely leads to [[deflagration]], which is much more likely to occur – the mix only has to be within [[inflammability limits]]. The combustion is much slower and does by itself not cause a shock wave. However, although the pressure rises less rapidly, the rise is still dramatic, especially if the volume is contained by an enclosure. If the enclosure cannot withstand the pressure, the gases will also expand explosively, as before.
:So I think a fuel–oxygen explosion can occur in open air, but for this to be an explosion in the strict sense of causing shock waves, the right conditions will only very rarely be fulfilled accidentally. (In thermobaric weapons, they are fulfilled by design.)  --[[User talk:Lambiam#top|Lambiam]] 09:05, 18 November 2024 (UTC)
::But in the conditions there is no requirement of an accidental event?! [[Special:Contributions/176.3.66.65|176.3.66.65]] ([[User talk:176.3.66.65|talk]]) 15:10, 22 November 2024 (UTC)
:::The OSHA fact sheet does not deal with ways to mitigate the risk of intentional explosions, such as may be caused by weapons. You are free to see this as an omission; I doubt though they will agree.  --[[User talk:Lambiam#top|Lambiam]] 12:00, 23 November 2024 (UTC)

== [[Delayed onset muscle soreness]] ==

How long does it last and how to recover from it? [[User:CometVolcano|CometVolcano]] ([[User talk:CometVolcano|talk]]) 16:53, 18 November 2024 (UTC)
:According to the article: "It peaks from 24 to 72 hours, then subsides and disappears up to seven days after exercise." --[[User:Amble|Amble]] ([[User talk:Amble|talk]]) 17:11, 18 November 2024 (UTC)
:From the top of this page: {{tq|We don't answer (and may remove) questions that require medical diagnosis.. }}. [[User:AndrewWTaylor|AndrewWTaylor]] ([[User talk:AndrewWTaylor|talk]]) 14:15, 19 November 2024 (UTC)
::It is said that the soreness is helped by consuming protein. [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 10:27, 20 November 2024 (UTC)

= November 20 =

== John Balbus and Steven Balbus ==

Are [[Steven Balbus]] (Oxford University astrophysicist) and John Balbus (Head of Office of Climate Change and Health Equity in Biden's [[United States Department of Health and Human Services|HHS]]) related? [[Special:Contributions/178.51.16.158|178.51.16.158]] ([[User talk:178.51.16.158|talk]]) 19:43, 20 November 2024 (UTC)

:Given their mutual association with Philadelphia and their strong physical resemblance, it seems very likely, but I haven't been able to find any source confirming it with a cursory web search, so this might take some deep digging (better suited to someone in the USA, not Europe). John Balbus, incidentally, seems to me to be a good candidate for a Wikipedia article. {The poster formerly known as 87.812.230.195} [[Special:Contributions/94.1.211.243|94.1.211.243]] ([[User talk:94.1.211.243|talk]]) 02:13, 21 November 2024 (UTC)
:They are brothers, with a third brother named Peter.[https://www.penncharter.com/about-us/news-media/news-details-page/~board/alumni/post/pc-profile-john-balbus-opc78] [https://issuu.com/penncharter/docs/pc_2023fallmagazine_final Here] on p. 33 is a photo of Steven en John side by side. Their father was Theodore G. Balbus,[https://www.legacy.com/us/obituaries/inquirer/name/theodore-balbus-obituary?id=10391295] a radiologist, and their mother Rita S. Frucht.[https://www.nytimes.com/1952/01/28/archives/rita-s-frucht-married-bride-of-dr-theodore-g-balbus-at-ceremony-in.html] A bio of the father is found [https://lm0610.wordpress.com/ here], where you can also find that Peter runs a consulting firm called Pragmaxis.  --[[User talk:Lambiam#top|Lambiam]] 10:09, 21 November 2024 (UTC)

= November 21 =

== Griffiths in math and physics ==

There's something called the [[arxiv:1009.0395|Griffiths phase]]. If you search for griffiths phase activity [https://arxiv.org/search/?query=griffiths+phase+activity&searchtype=all&source=header so], you'll find things with similar names. A Griffiths singularity, Griffiths effects, there's probably more than one thing people call Griffiths' formula since there's a physicist called [[Phillip Griffiths|Phillip]] and two named [[David J. Griffiths|David J. Griffiths]]. How many things are we dealing with under this name? Is there a book where they're all listed right next to each other? [[User:Gongula Spring|Gongula Spring]] ([[User talk:Gongula Spring|talk]]) 19:37, 21 November 2024 (UTC)

:The concept of a Griffiths phase is named after theoretical physicist [[Robert B. Griffiths]], who was the first to describe the appearance of such phases in an [[Ising model]] of [[ferromagnetism]].[https://journals.aps.org/prl/abstract/10.1103/PhysRevLett.23.17] He is also the eponym of the [[Griffiths inequality]]. Most uses of ''Griffiths singularity'' and ''Griffiths effect'' appear to be related. "Griffiths' formula" is a very general name that may refer to various formulas found by mathematicians with the surname Griffiths, such as Griffiths' integral formula for the [[Milnor number]] of an isolated hypersurface singularity, found by pure mathematician [[Philip A. Griffiths]], also the eponym of the [[Griffiths group]]. See also [[Griffiths' theorem]], named after yet another Griffiths.  --[[User talk:Lambiam#top|Lambiam]] 23:43, 21 November 2024 (UTC)
::[https://link.springer.com/article/10.1007/s10704-024-00786-3 That formulation] seems at least superficially be leading to references to [[Alan Arnold Griffith|Alan Arnold Griffith]]. Formulas like ''ohmic or non ohmic dissipation in metallic griffiths phases'' used at [https://allthingsfsu.blogspot.com/2017/08/fsu-lab-sets-new-magnet-strength-record.html the National High Magnetic Field Laboratory] then tend to appear ambiguous to that effect too. Most other examples are deeply plunging into statistical quanta states thus unambiguously associated with Robert B. Griffiths instead. --[[User:Askedonty|Askedonty]] ([[User talk:Askedonty|talk]]) 00:13, 22 November 2024 (UTC)
:::The bracketing is not as in ((Griffith phase) field theory) but like (Griffith ((phase field) theory)), a theory of fracture, based on a phase-field model, developed by Griffith.  --[[User talk:Lambiam#top|Lambiam]] 08:47, 22 November 2024 (UTC)
::::The interesting thing is that those approaches are leading us very near of a (a least to me ) finally rather satisfying view of the problematics induced by the idea of [[Action at a distance]]. --[[User:Askedonty|Askedonty]] ([[User talk:Askedonty|talk]]) 10:51, 22 November 2024 (UTC)
::::So much that you only have to think about it and what do you get? [https://arxiv.org/pdf/1111.5364#:~:text=Robert%20Griffiths%20begins%20his%20recent%20paper%20Quantum%20Locality,long%20distances%2C%20in%20apparent%20contradiction%20to%20special%20relativity%E2%80%9D. Long distances in apparent contradiction to..] --[[User:Askedonty|Askedonty]] ([[User talk:Askedonty|talk]]) 11:00, 22 November 2024 (UTC)
:::::I'm not sure if these long distances anticipate my next question, which is what does "long-range" mean in the [https://arxiv.org/search/?query=griffiths+phase+activity&searchtype=all&source=header search] results above?
:::::[[User:Gongula Spring|Gongula Spring]] ([[User talk:Gongula Spring|talk]]) 15:54, 22 November 2024 (UTC)
::::::Perhaps, as in #16 from that request as I get it "Temporal disorder in discontinuous non-equilibrium phase transitions: general results". The "long distances" discussion above being from 2002 by contrast. --[[User:Askedonty|Askedonty]] ([[User talk:Askedonty|talk]]) 16:39, 22 November 2024 (UTC)
:::::::Number 16 uses "temporal" and "critical" terms, are we getting toward [http://criticaloscillations.org/publications.html ideas] [[doi:10.1101/2022.12.14.519751|about]] long-range temporal correlations in critical brain dynamics? Are they spooky?
:::::::[[User:Gongula Spring|Gongula Spring]] ([[User talk:Gongula Spring|talk]]) 17:05, 22 November 2024 (UTC)
::::::::I don't think so. Or not so directly anyway. Number 16 seem to be about logic and geometry: distance in that context is fact, and can also be manipulated. Relevant quote if there was one regarding our subject - but their process define a temporal Griffiths inactive phase some time - relevant would be (see their pdf): ''
:::::::::Disorder due to spatial or temporal inhomogeneities is almost an unavoidable ingredient in many real systems, it is then desirable to understand their effects on these phase transitions. For continuous phase transitions, it was earlier recognized that spatial and temporal disorder changes the critical behavior whenever the generalized Harris criterion is violated [11, 12]: quenched spatial disorder is relevant whenever dν⊥ > 2 is violated while temporal disorder is relevant when νk = zν⊥ > 2 is violated; with ν⊥, νk and z being critical exponents of the clean phase transition and d being the number of spatial dimensions. Since the critical exponents of the directed percolation universality class violate the Harris criterion, it was then argued that this was the reason why it was '''never seen''' in experiments [13] (see however Ref. 14).''
::::::::(They describe their purpose as: ''Non-equilibrium phase transitions have constituted a rich and lively topic of research for many years. They occur in a wide variety of models in ecology [1], epidemic spreading [2], sociophysics [3], catalytic reactions [4], depinning interface growth [5, 6], turbulent flow [7], among other fields [8–10].'') [8–10] refer to Nonequilibrium Phase Transitions in Lattice Models. Sociophysics is a product of [[Positivism#Logical positivism]] ( perhaps note there a ''spooky'' "component not derived from observation" ) --[[User:Askedonty|Askedonty]] ([[User talk:Askedonty|talk]]) 21:03, 23 November 2024 (UTC)

= November 22 =

== Heat of chillies ==

How hot, in terms of Scovilles, does a chilli need to be before a parrot can feel the burn? I just saw a video on Facebook of a macaw eating a ghost pepper without the slightest care. From what I read, parrots are extremely resistant to the capsicum from chillies. Or is it because we have thousands of taste buds and parrots have tens, which is also true. [[Special:Contributions/146.90.140.99|146.90.140.99]] ([[User talk:146.90.140.99|talk]]) 01:27, 22 November 2024 (UTC)

:{{tq|“The seeds of Capsicum plants are dispersed predominantly by birds. In birds, the TRPV1 channel does not respond to [[capsaicin]] or related chemicals but mammalian TRPV1 is very sensitive to it. This is advantageous to the plant, as chili pepper seeds consumed by birds pass through the digestive tract and can germinate later, whereas mammals have molar teeth which destroy such seeds and prevent them from germinating.”}} [[User:Card_Zero| Card Zero ]] [[User_talk:Card_Zero|(talk)]] 03:22, 22 November 2024 (UTC)
:Yes, as Card Zero says, birds have different [[TRPV]] receptors (for [[vanilloids]] like capsaicin) than mammals. I guess chillis want their seeds distributed far and wide by birds. On the other hand, I've never seen anything eat the chillis that accidentally grow in my garden. Interestingly, my dog appears to have different TRPV receptors than me as they don't seem to notice very spicy chilli seeds on food and they won't be damaging the seeds. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 03:32, 22 November 2024 (UTC)
:Indeed, one of the most effective ways to keep squirrels off my bird feeder is to sprinkle the birdseed with chilli powder. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 09:23, 22 November 2024 (UTC)
::My entire home crop of capsicums (bell peppers to Americans), and some chillis disappeared in one night last summer right after a colony of fruit bats arrived in my local park. Fruit bats, of course, are mammals. [[User:HiLo48|HiLo48]] ([[User talk:HiLo48|talk]]) 10:08, 22 November 2024 (UTC)
:::That's interesting because there are many bats here. They often sleep individually or in small groups inside young banana leaves that haven't unfurled yet. They sometimes crash into me at night if I'm moving. I guess in bat-world tree-like things don't move. They seem to have a chilli-free diet but might eat some of the other fruit. Plenty of insects to eat. Bat teeth [https://www.nature.com/articles/s41467-023-40158-4 seem to be quite diverse] molar-wise. Chilli is the only thing that survives the wildlife. It's a multi-belligerent fruit-based forever war over resources with the birds, squirrels, rats, countless insects, fungi, bacteria and viruses. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 15:50, 22 November 2024 (UTC)
::::Insect eating bats are very different from the fruit bats. There's a theory that peppers have the same sort of relation to fruit bats as chillis do to birds so I can easily imagine a fruit bat being partial to a couple of chillis even if it does find them rather hot. [[User:NadVolum|NadVolum]] ([[User talk:NadVolum|talk]]) 21:23, 25 November 2024 (UTC)

= November 23 =

== Before [[Puberty]], sex organs are not functional? ==

How do sex organs function in both genders before puberty in humans? Not after [[Puberty]]. [[User:HarryOrange|HarryOrange]] ([[User talk:HarryOrange|talk]]) 07:24, 23 November 2024 (UTC)

:[[Sexual maturity]] is only reached during [[puberty]]. Before it is reached, the sex organs are not (or not yet fully) functional. See also {{section link|Sex organ#Development}} and [[Precocious puberty]].  --[[User talk:Lambiam#top|Lambiam]] 11:51, 23 November 2024 (UTC)
::They're functional. It's just that their functions are generally under the headings of "basic maintenance" and "not atrophying". [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 09:39, 24 November 2024 (UTC)
::To my understanding (which may be deficient), [[Testicle|testicles]] prior to puberty are secreting ''some'' levels of [[Androgen|androgens]] (including testosterone) ''and'' [[Estrogen|estrogens]], which contribute to the male body's normal development, even though these levels are well below what they become during and after puberty. I imagine (perhaps wrongly) that similar considerations apply to the [[Ovary|ovaries]].
::Our immediately relevant articles seem not very informative about pre-pubertal operations of the sex organs. Perhaps someone more knowlegable could take a look at them. [[Special:Contributions/94.1.211.243|94.1.211.243]] ([[User talk:94.1.211.243|talk]]) 09:46, 24 November 2024 (UTC)
:::I did take a look, I always do before answering a question. Here is a representative article; [https://academic.oup.com/humrep/article/29/1/97/629238 The immature human ovary shows loss of abnormal follicles and increasing follicle developmental competence through childhood and adolescence]. The word "competence" means that ''in vitro'' the ovary tissue does a better job of taking on adult functionality the older the girl, but ''in vivo'' such activity is suppressed. [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 10:08, 24 November 2024 (UTC)
::::Nevertheless, if I've understood the peripheral hints I've encountered, those pre-pubertal levels of androgen and estrogen (and steroid, etc.) secretions ''are'' necessary ''at the time'' (the pre-pubertal period) for ongoing normal development, which is kinda what the OP asked about. Of course, all this is well above my pay grade. {The poster formerly known as 87.81 230.195} [[Special:Contributions/94.1.211.243|94.1.211.243]] ([[User talk:94.1.211.243|talk]]) 13:36, 24 November 2024 (UTC)
:::::This discussion seems to have focused on the testicles and ovaries but the [[penis]] is also a sex organ and is capable of an [[erection]] before puberty. This is mentioned in our erection article in a sort of weird way given the flow on sentence. [[Ejaculation]] however only happens after puberty. I assume there is similarly some level of function in female sex organs. As mentioned in our [[masturbation]] article it's normal in children even in infancy and may even happen in the womb and is only a concern when there are indications it may relate to sexual abuse. [[User:Nil Einne|Nil Einne]] ([[User talk:Nil Einne|talk]]) 20:46, 24 November 2024 (UTC)

= November 25 =

== Is there a cryonic company that will freeze me while I'm still alive and healthy, and reanimate me 15 years later? If I arrest the aging process for 15 years this way, could I then pass for a Gen Z? ==

Could I have myself cryofrozen (without dying of another reason first) in 2025 with instructions to reanimate me in 2040 so that I could more convincingly pass for and live like someone born in the Gen Z generation?

What companies cryofreeze people who ask for it while still alive and healthy?

Or does such a cryonic plan and company exist anywhere in the world?

I wanted to be born in 2000, not the year I was actually born in. So if I get cryofrozen for enough years, I'll look as young as a Gen Z when I'm reanimated.

Lastly, Reddit's r/Cryonics subreddit's automoderator keeps glitching out because it keeps autoremoving any content of mine from there. I tried posting this question and above summary to other subreddits but their automod keeps autoremoving it too. Their persistent glitches kept bugging me enough to dust off the Wikipedian reference desk and post here again for the first time in many years. I used to be a regular on the refdesk, then moved to Reddit, and now I'm back. --[[Special:Contributions/2600:100A:B005:AFD5:B08A:71E6:8521:5D8E|2600:100A:B005:AFD5:B08A:71E6:8521:5D8E]] ([[User talk:2600:100A:B005:AFD5:B08A:71E6:8521:5D8E|talk]]) 01:48, 25 November 2024 (UTC)
:Short answer: No. As currently freezing a human adult, results in their death, as no resuscitation is possible. It would be some kind of murder to perform this, so only a crime syndicate would be willing. And then could you trust them for 15 years? [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 01:59, 25 November 2024 (UTC)
::{{small|In 15 years, you'd be just as deceased, pushing up daisies, no more, pining for the fjords. So what's trust got to do with it? [[User:Clarityfiend|Clarityfiend]] ([[User talk:Clarityfiend|talk]]) 08:34, 25 November 2024 (UTC)}}

::{{small|At this point I feel bound to recommend that you watch ''[[Sleeper (1973 film)|Sleeper]]''.[[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 10:07, 25 November 2024 (UTC)}}

::Terraforming a planet around some distant star and setting up a population there sounds far easier and actually doable to me. Perhaps in the far future it'll be possible to create a new body and copy the brain fom one of those frozen blocks for it, or maybe set up an android with an artificial copied brain - but why would any people who could do that bother with anyone from this time, would it be ethical for us to try and make a Neanderthal clone? [[User:NadVolum|NadVolum]] ([[User talk:NadVolum|talk]]) 21:15, 25 November 2024 (UTC)

:::By way of a reference, try [https://www.livescience.com/health/death/we-dont-yet-have-the-know-how-to-properly-maintain-a-corpse-brain-why-cryonics-is-a-non-starter-in-our-quest-for-immortality '''We don't yet have the know-how to properly maintain a corpse brain': Why cryonics is a non-starter in our quest for immortality'']. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 11:53, 26 November 2024 (UTC)

== Can any insurance company make a cryonics bankruptcy insurance policy for companies that preserve bodies in cryogenic preservation vats so that even when the company goes bankrupt, their insurance policies will keep these vats running and bodies preserved? ==

...So that we can continue the hope and possibility of reanimating these bodies back to life when medical science advances and finds cures to reverse whatever they died from?

This topic was also autoremoved from r/Cryonics so that's why I'm bringing it here too. Thanks in advance. --[[Special:Contributions/2600:100A:B005:AFD5:B08A:71E6:8521:5D8E|2600:100A:B005:AFD5:B08A:71E6:8521:5D8E]] ([[User talk:2600:100A:B005:AFD5:B08A:71E6:8521:5D8E|talk]]) 01:48, 25 November 2024 (UTC)

:An [[insurance policy]] defines the amount of money to be paid to the holder of the policy when a specified contingency occurs. If the contingency is [[bankruptcy]] and the idea is to keep the company running, the amount should be larger than the prospectively unknowable debt to [[preferential creditor]]s. It should be obvious that no insurance company can offer a policy with an unlimited payout. Apart from this, even an insurance for a sufficiently large amount cannot guarantee that the company or [[Trustee in bankruptcy|trustee]] will use the money paid out for the intended purpose.  --[[User talk:Lambiam#top|Lambiam]] 02:53, 25 November 2024 (UTC)
::Who would be a creditor? They're all dead and have no rights. [[User:NadVolum|NadVolum]] ([[User talk:NadVolum|talk]]) 21:00, 25 November 2024 (UTC)
:::Creditors of Instant Immortality (the bankrupt cryonics company, for short II) could be: (1) the tax office; (2) II's bank; (3) the company from which II hired its cryogenic equipment; (4) II's provider of liquid nitrogen; (5) II's lawyers; (6) scores of estates of frozen clients, legally presumed dead, who won a class action lawsuit against II.  --[[User talk:Lambiam#top|Lambiam]] 11:43, 26 November 2024 (UTC)

:Wow, is it April 1 already? ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 01:00, 26 November 2024 (UTC)
:Cryonics is such a blatant scam I don't understand how it is legal. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 09:33, 26 November 2024 (UTC)
::More blatant than (also legal) [[homeopathy]]? [[User:Clarityfiend|Clarityfiend]] ([[User talk:Clarityfiend|talk]]) 10:06, 26 November 2024 (UTC)

A marginally better idea might be to create a [[testamentary trust]] fund, if you could find a willing trustee. I'm not sure how far into the future you might want this to extend (do frozen corpses have a "best before" date?) but a legal expert might advise on how to extend the trust beyond the lifetime of the trustee, and what incentives might be required for another person to accept that role. [[User:Alansplodge|Alansplodge]] ([[User talk:Alansplodge|talk]]) 11:45, 26 November 2024 (UTC)

== Where to verify a chemical compund name synonyms? ==

The [[ARM390]] compound has multiple IDs, (some of?) which can be found at PubChem here:
: https://pubchem.ncbi.nlm.nih.gov/compound/9841259#section=Synonyms
There are two among them, which differ with one ''zero'' only: [[AR-M1000390]] and [[AR-M100390]]. The difference seems too small to be just a coincidence, it looks like one must be a typo modification of the other.

Is there any way for a non-chemistry/medicine-professional to trace the origin of those specific symbols and learn whether they are actually the same, or genuinely different? --[[User:CiaPan|CiaPan]] ([[User talk:CiaPan|talk]]) 08:09, 25 November 2024 (UTC)

PS. The motivation for publishing this question here is it's not only me in doubt – another user called for discussion at [[Wikipedia:Redirects for discussion/Log/2024 November 24#AR-M100390|Redirect discussion: AR-M100390]]. The sources refer to both names, so from the Wikpedia point of view both are valid, but... Out of curiosity, I just would like to know: are they independent, truly different? [[User:CiaPan|CiaPan]] ([[User talk:CiaPan|talk]])
:Usually, I would trust [[ChemSpider]] to validate such synonyms and that's where I'd send a non-expert. In this particular case, Chemspider seems to prefer AR-M1000390 but one possible source of misinformation/typo is [https://pmc.ncbi.nlm.nih.gov/articles/PMC2672171/ this paper], which consistently uses AR-M100390 in the text ''but'' AR-M1000390 in the citation #23, which is correct at [[doi:10.1016/S0024-3205(03)00489-2]]. [[User:Michael D. Turnbull|Mike Turnbull]] ([[User talk:Michael D. Turnbull|talk]]) 12:14, 25 November 2024 (UTC)

:The earliest use of the name AR-M1000390 seems to be in a PhD thesis from 2003.[https://theses.fr/2003PA05P602] The same name was used in a 2003 journal article in ''[[Life Sciences (journal)|Life Sciences]]'' describing the results of this PhD thesis.[https://www.sciencedirect.com/science/article/abs/pii/S0024320503004892?via%3Dihub] The substance was synthesized by researchers from AstraZeneca R&D; their paper describing the design, synthesis, and pharmacological evaluation of the drug, published in 2000, does not use this name, but only the systemic name ''N'',''N''-diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide.[https://pubmed.ncbi.nlm.nih.gov/11052794/] Plausibly, the "AR" bit is short for "AstraZeneca R&D" and the whole was originally a code for internal use in the AstraZeneca lab. Subsequently:
:* '''AR-M1000390''' was deposited on 2016-02-05; the source was the [[Guide to Pharmacology|IUPHAR/BPS Guide to PHARMACOLOGY]],[https://pubchem.ncbi.nlm.nih.gov/substance/310264783/version/1] which references the 2003 ''Life Sciences'' article.[https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=9005]
:* The synonym '''ar-m100390''' was deposited on 2017-09-13 by Springer Nature.[https://pubchem.ncbi.nlm.nih.gov/substance/341355739]
:* Yet another synonym: '''AR-M 1000390''', deposited on 2024-11-14 by a chemical vendor.[https://pubchem.ncbi.nlm.nih.gov/substance/504088734]
:--[[User talk:Lambiam#top|Lambiam]] 20:02, 25 November 2024 (UTC)

:: Thank you both, [[User:Michael D. Turnbull|Mike Turnbull]] and [[User:Lambiam|Lambiam]], for detailed info. {{=D}} [[User:CiaPan|CiaPan]] ([[User talk:CiaPan|talk]]) 07:24, 26 November 2024 (UTC)

= November 27 =

== Right whales and Left whales ==

Why are there [[right whale]]s, but not [[left whale]]s? [[User:Someone who's wrong on the internet|Someone who's wrong on the internet]] ([[User talk:Someone who's wrong on the internet|talk]]) 09:05, 27 November 2024 (UTC)
:Perhaps there's a naming dispute in the whale courts over brand names, a left vs wrong case. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 09:32, 27 November 2024 (UTC)

:You're thinking of the [[Narwhal]]. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 10:00, 27 November 2024 (UTC)
:Not right versus left, but right versus wrong. This was the right species to catch. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 10:10, 27 November 2024 (UTC)
:Th answer is in the article you linked: [[Right_whale#Naming]]. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 11:27, 27 November 2024 (UTC)

:If a member of a group of whales manages to beach itself, and the others swim on, then the one on the beach would be a left whale. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 15:11, 27 November 2024 (UTC)
::What is a [[wrong whale]] exactly? [[User:Someone who's wrong on the internet|Someone who's wrong on the internet]] ([[User talk:Someone who's wrong on the internet|talk]]) 23:19, 27 November 2024 (UTC)
:::The ones that don't fit the definition given in the article. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 23:42, 27 November 2024 (UTC)
::::There's also this:[https://x.com/davidcoverdale/status/1153914897987538946] ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 23:45, 27 November 2024 (UTC)

== Lawson Criterion: calculating energy density W ==

[[Lawson Criterion|Lawson Criterion]]

The article states:
Ion density then equals electron density and the energy density of both electrons and ions together is given by

<math>W = 3nT</math>

where <math>T</math> is the temperature in electronvolt (eV) and <math>n</math> is the particle density.

However, there is no clear explanation given as to why the energy density equals 3nT, rather than 2nT or just nT. If the electrons and ions are in equal parts within the plasma, shouldn't it equal 2nT?

Is there any source that clears this up? — Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[User:Shouldputsomethinginterestinghere|Shouldputsomethinginterestinghere]] ([[User talk:Shouldputsomethinginterestinghere#top|talk]] • [[Special:Contributions/Shouldputsomethinginterestinghere|contribs]]) 11:28, 27 November 2024 (UTC) 
[[User:Shouldputsomethinginterestinghere|Shouldputsomethinginterestinghere]] ([[User talk:Shouldputsomethinginterestinghere|talk]]) 11:27, 27 November 2024 (UTC)
:The energy density of a [[monoatomic gas]] is <math>E=\frac{3}{2}nT</math>. Both electrons and ions can be considered monoatomic gases, so the total energy density is double of that value. [[User:Ruslik0|Ruslik]]_[[User Talk:Ruslik0|Zero]] 20:56, 27 November 2024 (UTC)
::Depends on what ''n'' is precisely. If ''n'' is the ion density (equal to the electron density), then <math>2\cdot\frac{3}{2}nT</math> is correct. If taken literally as "particle density" (i.e. ions and electrons combined), then it should still be <math>\frac{3}{2}nT</math>. I assume that the former is meant, but the formulation seems ambiguous. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 21:39, 27 November 2024 (UTC)

== stage 4 breast cancer ==

I'm not seeking medical advice, but stage 4 cancer means you're gonna die from it imminently, can someone confirm? Or is it [https://www.yahoo.com/lifestyle/former-mtv-vj-ananda-lewis-184257672.html wait, what??] Maybe I'm confused. Thanks. [[Special:Contributions/2601:644:8581:75B0:0:0:0:6B00|2601:644:8581:75B0:0:0:0:6B00]] ([[User talk:2601:644:8581:75B0:0:0:0:6B00|talk]]) 22:22, 27 November 2024 (UTC)

= November 28 =

== Are there any volatile gold compounds? ==

Title. Let's say "boiling point under 500°C" counts (as long as it actually boils and doesn't decompose). :) [[User:Double sharp|Double sharp]] ([[User talk:Double sharp|talk]]) 03:11, 28 November 2024 (UTC)
:[[Gold(III) fluoride]] apparently undergoes "sublimation above 300 °C". Tracing the dewiki article's data suggests this comes from CRC 10th ed. [[doi:10.1016/0022-328X(87)80355-8]] is a lead article about volatile gold compounds, but these (and others I found) are generally about transferring as a vapor for CVD, nanoparticle formation, or other short-timeframe processes, so probably low pressure and maybe not highly stable in the vapor phase. [[User:DMacks|DMacks]] ([[User talk:DMacks|talk]]) 03:58, 28 November 2024 (UTC)
:The compound [Me2AuOSiMe3]2 sublimes at 40 °C (0.001 mmHg) without decomposition. ([[doi|10.1002/anie.196706831]]) --[[User:Leiem|Leiem]] ([[User talk:Leiem|talk]]) 04:24, 28 November 2024 (UTC)

2024 Zhuhai car attack

2024-11-16T18:22:00Z

Leiem: /* See also */ + Massacre happened in Yixing, China

{{Short description|Mass casualty event in China}}
{{Use dmy dates|date=November 2024}}
{{Infobox civilian attack
| image = Zhuhai Stadium west gate after 2024 Zhuhai car attack - Nov.12,2024.jpg
| caption = Mourners at the west gate of Zhuhai Sports Center the day after the attack
| location = [[Zhuhai]], Guangdong, China
| date = 11 November 2024
| time = 19:48 [[China Standard Time|CST]] ([[UTC+08:00]])
| type = [[Vehicle-ramming attack]]
| weapon = [[Beijing BJ40]]
| fatalities = 35
| injuries = 44 (including the perpetrator)
| perpetrator =
| motive = Dissatisfaction with the division of marital property from his divorce<ref name="AP12" />
| coordinates = {{Coord|id = Q131152711|type:event_region:CN-GD-04|display=inline,title}}
| map = {{Infobox mapframe
| id = Q131152711
| zoom = 15
| shape-fill-opacity=0.4
| marker = road-accident
}}
| map_caption = Location of Zhuhai Sports Center in Zhuhai, Guangdong, China
}}

On 11 November 2024, the driver of an [[SUV]] launched a [[vehicle-ramming attack]] against people on the exercise track at the [[Zhuhai Stadium]] sports center in [[Zhuhai]], Guangdong, China, resulting in 35 deaths and 43 injuries.<ref name=":1" /> Afterward, the driver was taken into custody and sent to a hospital after harming himself with a knife.<ref name=":1" /> The man is believed to have been motivated by anger over a recent [[divorce settlement]].<ref name="reutersnov12">{{Cite web |date=12 November 2024 |title=Zhuhai car attack: China clears memorial as government scrambles to respond |url=https://www.reuters.com/world/china/chinas-leaders-urge-investigation-into-zhuhai-car-attack-that-killed-35-2024-11-13/ |first1=David |last1=Kirton |first2=Nicoco |last2=Chan |access-date=12 November 2024 |website=Reuters}}</ref>

Videos and coverage of the attack were censored online and details about it were not released until the day after the attack.<ref name=":4">{{Cite news |last=Kirton |first=David |date=12 November 2024 |title=Zhuhai car attack kills 35 as driver rams into crowd in southern China |url=https://www.reuters.com/world/china/chinese-police-detain-man-after-hit-and-run-attack-leaves-several-wounded-2024-11-12/ |access-date=12 November 2024 |work=[[Reuters]]}}</ref><ref name="AP12">{{cite web |last=Huizhong |first=Wu |last2=Ng |first2=Han Guan |date=11 November 2024 |title=Driver rams his car into crowd in China, killing 35. Police say he was upset about his divorce |url=https://apnews.com/article/china-crash-crowd-zhuhai-3db25fd49b1313c462bbf4e0214f3834 |access-date=12 November 2024 |website=[[Associated Press]] |language=en}}</ref> This caused tension on Chinese social media platforms, with people angered by the delay in publication of details.<ref name="reutersnov12" />

It was the deadliest single attack in China since the [[May 2014 Ürümqi attack]].<ref name="Bloomberg12">{{Cite web |last=Wong |first=Foster |last2=Xiao |first2=Josh |date=12 November 2024 |title=Driver Kills 35 in China's Deadliest Attack in at Least a Decade |url=https://www.msn.com/en-us/news/world/chinese-driver-kills-35-in-deadliest-attack-in-at-least-a-decade/ar-AA1tWCVs |access-date=13 November 2024 |website=[[MSN]] |publisher=[[Bloomberg News]]}}</ref><ref name="reutersnov12"/><ref name="Shawn1">{{cite news |last1=Gan |first1=Nectar |last2=Deng |first2=Shawn |last3=Danaher |first3=Caitlin |date=13 November 2024 |title=35 killed after driver plows car into crowds at sports center in China's deadliest known attack in a decade |url=https://www.cnn.com/2024/11/12/china/china-zhuhai-hit-and-run-intl-hnk/index.html |access-date=14 November 2024 |publisher=[[CNN]] |archive-date=13 November 2024 |archive-url=https://web.archive.org/web/20241113202130/https://www.cnn.com/2024/11/12/china/china-zhuhai-hit-and-run-intl-hnk/index.html |url-status=live }}</ref>

==Attack==
[[File:Zhuhai stadium pedestrian walkway en.svg|thumb|left|A map of the sports center. The path the driver took through the walking track is marked in red.]]

There was heightened security in Zhuhai, which was to host a major civil and military [[Air show|airshow]] the next day, the [[China International Aviation & Aerospace Exhibition]] (Zhuhai Airshow).<ref>{{cite news |last1=Gan |first1=Nectar |date=12 November 2024 |title=35 killed after car plows into crowds outside sports center in Chinese city, police say |url=https://edition.cnn.com/2024/11/12/china/china-zhuhai-hit-and-run-intl-hnk/index.html |access-date=12 November 2024 |work=CNN |language=en}}</ref>

At approximately 19:48 (GMT+8)<ref>{{Cite web |last=Dang |first=Yuanyue |date=12 November 2024 |title=35 dead after car attack in Chinese city of Zhuhai, suspect arrested, police say |url=https://www.scmp.com/news/china/politics/article/3286259/35-dead-chinese-car-attack-crowd-suspect-arrested-police-say |url-status=live |archive-url=https://web.archive.org/web/20241112152524/https://www.scmp.com/news/china/politics/article/3286259/35-dead-chinese-car-attack-crowd-suspect-arrested-police-say |archive-date=12 November 2024 |access-date=12 November 2024 |website=[[South China Morning Post]] |language=en}}</ref> on 11 November 2024, an attacker drove an [[SUV]] at {{Convert|70|-|80|km/h|abbr=on}} into people while around 300 of them were exercising at the [[Zhuhai Stadium|Zhuhai Sports Center]] running track.<ref name="scmpnov14">{{Cite news |last=Dang |first=Yuanyue |last2=Zhang |first2=Phoebe |last3=Wang |first3=Amber |last4=Wong |first4=Hayley |date=14 November 2024 |title=Zhuhai car attack victims heard sound 'like earthquake' but had no time to escape: Witness |url=https://www.scmp.com/news/china/politics/article/3286435/zhuhai-car-attack-victims-heard-sound-earthquake-had-no-time-escape-witness |access-date=14 November 2024 |publisher=[[South China Morning Post]] |language=en}}</ref><ref name=":2">{{Cite web |last=Alund |first=Natalie Neysa |date=12 November 2024 |title=Driver rams SUV into crowd exercising in Zhuhai, China leaving 35 dead, dozens injured |url=https://www.usatoday.com/story/news/world/2024/11/12/china-car-crash-hit-run-driver-crowd-zhuhai/76216436007/ |access-date=13 November 2024 |website=[[USA Today]] |language=en-US}}</ref> An eyewitness said that the driver drove in a loop on the [[running track]], striking many people.<ref name="BBC13">{{cite news |title=Zhuhai: Dozens killed in car rampage through Chinese stadium |url=https://www.bbc.com/news/articles/cwy1k2rx724o |first1=Stephen |last1=McDonell |authorlink=Stephen McDonell |first2=Frances |last2=Mao |date=13 November 2024 |access-date=13 November 2024 |work=[[BBC News]]}}</ref>

Some victims were wearing sports uniforms of a local exercise group.<ref>{{cite web |date=12 November 2024 |title=越野車來回撞珠海體園10死百傷 62歲男司機被捕部分傷者屬長者健步團 – 20241112 – 中國 |trans-title=An off-road vehicle crashed into the Zhuhai Sports Park, killing 10 and injuring hundreds. A 62-year-old male driver was arrested. Some of the injured were members of an elderly walking group. |url=https://news.mingpao.com/pns/%E4%B8%AD%E5%9C%8B/article/20241112/s00013/1731349733133/%E8%B6%8A%E9%87%8E%E8%BB%8A%E4%BE%86%E5%9B%9E%E6%92%9E-%E7%8F%A0%E6%B5%B7%E9%AB%94%E5%9C%9210%E6%AD%BB%E7%99%BE%E5%82%B7-62%E6%AD%B2%E7%94%B7%E5%8F%B8%E6%A9%9F%E8%A2%AB%E6%8D%95-%E9%83%A8%E5%88%86%E5%82%B7%E8%80%85%E5%B1%AC%E9%95%B7%E8%80%85%E5%81%A5%E6%AD%A5%E5%9C%98 |url-status=live |archive-url=https://web.archive.org/web/20241112051657/https://news.mingpao.com/pns/%E4%B8%AD%E5%9C%8B/article/20241112/s00013/1731349733133/%E8%B6%8A%E9%87%8E%E8%BB%8A%E4%BE%86%E5%9B%9E%E6%92%9E-%E7%8F%A0%E6%B5%B7%E9%AB%94%E5%9C%9210%E6%AD%BB%E7%99%BE%E5%82%B7-62%E6%AD%B2%E7%94%B7%E5%8F%B8%E6%A9%9F%E8%A2%AB%E6%8D%95-%E9%83%A8%E5%88%86%E5%82%B7%E8%80%85%E5%B1%AC%E9%95%B7%E8%80%85%E5%81%A5%E6%AD%A5%E5%9C%98 |archive-date=12 November 2024 |access-date=13 November 2024 |website=[[Ming Pao]] |language=zh-HK}}</ref> According to a witness, most of the victims were middle-aged or elderly people in exercise groups. There were typically six or seven groups walking at the sports complex every day, accompanied by music. The loud music may have muffled the initial sounds of the attack, leaving people little time to react.<ref>{{cite web |last1=林 |first1=煇智 |date=13 November 2024 |title=珠海致命撞车事件目击者：受害者大多数是中老年人 |trans-title=Eyewitnesses of fatal car crash in Zhuhai: Most of the victims were middle-aged and elderly people |url=https://www.zaobao.com.sg/realtime/china/story20241113-5339230 |url-status=live |archive-url=https://web.archive.org/web/20241113141915/https://www.zaobao.com.sg/realtime/china/story20241113-5339230 |archive-date=13 November 2024 |access-date=13 November 2024 |website=[[Lianhe Zaobao]] |language=zh-SG}}</ref>

The architect who designed the fitness center told ''[[Lianhe Zaobao]]'' that vehicles are not allowed on the track, which has stone bollards and fences set up all around it. He suspected that the perpetrator drove into the area from the other side of the stadium.<ref>{{cite web |last1=林 |first1=煇智 |last2=黎 |first2=康 |date=13 November 2024 |title=珠海越野车撞人35死43伤学者：官方如何化解社会戾气至关重要 |trans-title=An off-road vehicle hit 35 people in Zhuhai, killing 35 and injuring 43. Scholar: How officials resolve social violence is crucial |url=https://www.zaobao.com.sg/news/china/story20241112-5336356 |url-status=live |archive-url=https://web.archive.org/web/20241113111649/https://www.zaobao.com.sg/news/china/story20241112-5336356 |archive-date=13 November 2024 |accessdate=14 November 2024 |website=[[Lianhe Zaobao]] |language=zh-SG}}</ref>

On 12 November, Zhuhai Police said that the attack resulted in 35 deaths and 43 injuries.<ref name=":1" /> On 13 November, the [[Ministry of Foreign Affairs of China]] said that no [[Foreign national|foreign nationals]] were among the victims.<ref>{{cite web |last1=Jett |first1=Jennifer |last2=Austin |first2=Henry |date=13 November 2024 |title=China removes memorials and censors online outrage after deadly car attack |url=https://www.nbcnews.com/news/world/zhuhai-car-attack-china-removes-memorials-censors-online-outrage-rcna179917 |access-date=13 November 2024 |website=[[NBC News]] |language=en}}</ref><ref>{{cite news |date=13 November 2024 |title=China snuffs out memorials to victims of deadly car rampage |url=https://www.straitstimes.com/asia/east-asia/china-clears-makeshift-memorial-to-victims-of-deadly-car-ramming-attack |access-date=14 November 2024 |work=[[The Straits Times]] |publisher=}}</ref>

==Suspect==
According to a police statement, the alleged attacker was a 62-year-old divorced man with the surname [[Fán (surname)|Fan]] ({{lang-zh|樊}}).<ref name=":1" /> He was arrested while trying to flee the scene.<ref name=Shawn1 /> He was found unconscious with wounds to his neck consistent with [[self-harm]] in his car and was taken to hospital for treatment.<ref name=":1" /> Police said that Fan entered a [[coma]] after he cut himself in the neck and chest with a knife.<ref>{{Cite news |date=12 November 2024 |title=At least 35 killed in China car ramming |url=https://www.aljazeera.com/news/2024/11/12/dozens-killed-in-china-car-ramming |access-date=12 November 2024 |work=[[Al Jazeera English|Al Jazeera]] |language=en |agency=}}</ref><ref>{{cite news |title=China removes memorials to car ramming attack victims amid public outrage |url=https://www.aljazeera.com/news/2024/11/13/china-removes-memorials-to-car-ramming-attack-victims-amid-public-outrage |access-date=14 November 2024 |agency=Al Jazeera |date=13 November 2024}}</ref> Early reports claimed that the attack stemmed from discontent over the financial settlement of his divorce.<ref name=":2" /><ref name=":1">{{Cite web |date=12 November 2024 |title=Dozens killed in Zhuhai, China, by driver who rammed car into crowd ahead of military expo, police say |url=https://www.cbsnews.com/news/car-rams-crowd-china-zhuhai-dozens-dead/ |access-date=12 November 2024 |website=[[CBS News]] |language=en-US |publication-place=Bangkok}}</ref><ref name="AP12" /> Journalists have noted China's economic downturn may be a contributing factor, suggesting relations between the trend of random attacks and the economic downturns and rising social pressures of the country.{{refn|<ref>{{Cite web |date=12 November 2024 |title=中国の車暴走事件日本大使館が滞在の日本人に注意呼びかけ |trans-title=Runaway car incident in China: Japanese embassy warns Japanese residents to be careful |url=https://www3.nhk.or.jp/news/html/20241112/k10014636041000.html |access-date=12 November 2024 |website=[[NHK]] |lang=ja-JP}}</ref><ref>{{Cite news |last=乾 |first=朗 |date=12 November 2024 |title=越野车冲撞珠海民众35人死亡43人受伤社媒视频被急删 |trans-title=Off-road vehicle crashes into people in Zhuhai, 35 killed, 43 injured, social media video has been deleted |url=https://www.rfa.org/mandarin/yataibaodao/shehui/ql1-zhuhai-vehicle-randomattack-revenge-11122024013819.html |accessdate=13 November 2024 |work=[[Radio Free Asia]] |language=zh-cn}}</ref><ref>{{cite web |date=13 November 2024 |title=中國報復社會暴力事件頻生官方披露少真相難知 |trans-title=Violence in retaliation against society in China is frequent, with few official disclosures and it is difficult to know the truth |url=https://www.cna.com.tw/news/acn/202411130281.aspx |accessdate=13 November 2024 |website=[[Central News Agency (Taiwan)|Central News Agency]] |publisher= |lang=zh-TW}}</ref><ref name="Bloomberg12" /><ref name="reutersnov12" />}} A [[Chinese politics]] expert from the [[University of California]] said that with low domestic demand and the popped [[Chinese property sector crisis (2020–present) |property bubble]], Chinese families' wealth is diminishing overall, which would lead to tension in Chinese society and may have been a contributing factor in this attack.<ref>{{cite web |date=12 November 2024 |title=At Least 35 Killed After Man Drives Into Crowd in Southern China |url=https://www.nytimes.com/2024/11/12/world/asia/china-car-attack-zhuhai.html |url-access=subscription |archiveurl=https://archive.is/dhAwS |archivedate=13 November 2024 |accessdate=13 November 2024 |work=The New York Times}}</ref>

The vehicle purportedly used in the attack was a [[Beijing BJ40]], a large [[off-road vehicle]] weighing about 2 tonnes and worth around [[Renminbi|CNY]] 200,000 ([[United States dollar|US$]]31,000) and was bought from a local sales store. Fan purchased the car through a loan a week before the attack and picked it up on 10 November, the day before the attack.<ref>{{cite web |last1=林 |first1=煇智 |date=13 November 2024 |title=珠海撞人案涉事越野车宽近两米嫌犯事发前一天提车 |trans-title=The off-road vehicle involved in the Zhuhai collision case was nearly two meters wide. The suspect picked up the vehicle the day before the incident. |url=https://www.zaobao.com.sg/realtime/china/story20241113-5340022 |access-date=13 November 2024 |website=[[Lianhe Zaobao]] |language=zh-SG}}</ref>

==Aftermath==
[[File:Zhuhai Stadium west gate on Nov.12,2024.jpg|upright=1.5|thumb|West gate of the stadium on the day after the attack]]

Shortly after the attack, many local residents went to hospitals and blood banks to donate blood, forming long queues overnight.<ref>{{cite web |last=Lim |first1=Joyce ZK |date=13 November 2024 |title=Residents in China's Zhuhai city reel from deadly car rampage |url=https://www.straitstimes.com/asia/east-asia/residents-in-zhuhai-city-reel-from-deadly-car-rampage |access-date=13 November 2024 |website=[[The Straits Times]]}}</ref><ref>{{cite web |date=13 November 2024 |title=Outpouring of blood donations in China's Zhuhai as residents rally to help car ramming victims |url=https://www.channelnewsasia.com/east-asia/china-zhuhai-car-ramming-blood-donations-support-injured-4745956 |access-date=13 November 2024 |website=[[CNA (TV network)|CNA]] |language=en}}</ref><ref>{{cite web |last=朱 |first=加樟 |date=12 November 2024 |title=珠海車撞人35死43傷｜捐血站排長龍大量市民自發通宵排隊捐血 |trans-title=Zhuhai car hit 35 people, killed 43 and injured Long queues at blood donation stations, a large number of citizens spontaneously queued up all night to donate blood |url=https://www.hk01.com/%E5%8D%B3%E6%99%82%E4%B8%AD%E5%9C%8B/1075452/%E7%8F%A0%E6%B5%B7%E8%BB%8A%E6%92%9E%E4%BA%BA35%E6%AD%BB43%E5%82%B7-%E6%8D%90%E8%A1%80%E7%AB%99%E6%8E%92%E9%95%B7%E9%BE%8D-%E5%A4%A7%E9%87%8F%E5%B8%82%E6%B0%91%E8%87%AA%E7%99%BC%E9%80%9A%E5%AE%B5%E6%8E%92%E9%9A%8A%E6%8D%90%E8%A1%80#google_vignette |access-date=13 November 2024 |website=[[HK01]] |language=zh-HK}}</ref>

A makeshift memorial was created at the location of the attack, but Chinese authorities quickly began removing wreaths, candles, and alcohol placed there, while cordoning off access to a makeshift vigil area.<ref name="reutersnov12" /> The police at the location told visitors that there were "hostile foreign forces with malicious intentions," according to the ''[[South China Morning Post]]''.<ref name=scmpnov14/>

Local officials including the [[Chinese Communist Party Committee Secretary|Chinese Communist Party (CCP) Committee Secretary]] and mayor arrived at the scene to oversee the rescue operations and establish a task force to expedite medical treatment for the injured, investigate the attack, and support the victims' families. The Zhuhai Sports Center issued a notice at around 9 p.m. on 11 November, announcing the immediate suspension of operations.<ref>{{cite news |date=11 November 2024 |title=珠海市体育中心即刻起暂停开放 |trans-title=Zhuhai Sports Center will be temporarily closed with immediate effect |url=https://pub-zhtb.hizh.cn/a/202411/11/AP67320b16e4b06862d645c045.html |accessdate=12 November 2024 |publisher=[[Zhuhai Stadium]] |language=zh}}</ref> [[General Secretary of the Chinese Communist Party|General Secretary of the CCP]], [[Xi Jinping]], along with [[Premier of China|Premier]] [[Li Qiang]], issued directives on the evening of 12 November, calling for all efforts to treat the injured, severe punishment of the perpetrator according to the law, and measures to mitigate societal risks.<ref>{{cite news |date=12 November 2024 |title=习近平对广东珠海市驾车冲撞行人案件作出重要指示 |trans-title=Xi Jinping issued important instructions on the case of driving into pedestrians in Zhuhai City, Guangdong Province |url=https://h.xinhuaxmt.com/vh512/share/12275438 |accessdate=12 November 2024 |work=[[Xinhua News Agency]] |language=zh}}</ref> [[Huang Kunming]], [[Politburo of the Chinese Communist Party|CCP Politburo]] member and [[Chinese Communist Party Committee Secretary|CCP Secretary]] of Guangdong, held a series of video conferences following the attack, including a special session of the Guangdong Provincial Committee for Building a Safe Guangdong.<ref>{{cite news |last=张 |first=文单 |last2=应 |first2=立枫 |date=12 November 2024 |title=广东召开会议传达学习习近平总书记对珠海市驾车冲撞行人案件作出的重要指示精神：全力以赴做好伤员救治和调查处置工作，举一反三开展问题排查整治 |trans-title=Guangdong held a meeting to convey and study the important instructions given by General Secretary Xi Jinping on the case of driving into pedestrians in Zhuhai City: go all out to treat the injured, investigate and deal with them, and draw inferences from one example to carry out problem investigation and rectification |url=https://pub-zhtb.hizh.cn/a/202411/12/AP67333ea7e4b080be7be6c44f.html |work=[[Nanfang Daily|Southern+]] |language=zh |agency=}}</ref><ref>{{cite news |last=李 |first=森 |date=13 November 2024 |title=市委常委会召开会议认真传达学习习近平总书记对珠海市驾车冲撞行人案件作出的重要指示精神 |trans-title=The Standing Committee of the Municipal Party Committee convened a meeting to earnestly convey and study the spirit of the important instructions given by General Secretary Xi Jinping on the case of driving into pedestrians in Zhuhai City |url=https://pub-zhtb.hizh.cn/a/202411/13/AP67339285e4b080be7be6cc1e.html |work=Zhuhai Daily |language=zh}}</ref>

On 12 November, [[Japan]]'s embassy in China warned its nationals about personal security issues in China, advising Japanese people not to speak Japanese loudly in public.<ref name="BBC13" /> [[Chief Cabinet Secretary]] [[Yoshimasa Hayashi]] expressed condolences and sympathy for the victims and families, and stated that no Japanese citizens were among the victims according to current reports.<ref>{{cite web |date=13 November 2024 |title= |script-title=ja:中国車が暴走 35人死亡43人けが現場で住民が花を手向け追悼 |trans-title=China: 35 people killed and 43 injured when car runs out of control; residents lay flowers and mourn at scene |url=https://www3.nhk.or.jp/news/html/20241113/k10014636741000.html |url-status=live |archiveurl=https://archive.is/XGyGB |archivedate=13 November 2024 |accessdate=13 November 2024 |website=[[NHK]] |publisher= |language=ja}}</ref>

===Censorship by Chinese authorities===
Internet searches are usually heavily monitored prior to major events in China, thus, searches for the event and what happened were originally censored due to the upcoming [[China International Aviation & Aerospace Exhibition|Zhuhai Airshow]].<ref name="AP12" /> During the first hours after the attack, Chinese media outlets were told not to report on the issue, according to [[BBC News]].<ref name="BBCrevenge">{{cite news |last1=Ng |first1=Kelly |date=13 November 2024 |title='Taking revenge on society': Deadly car attack sparks questions in China |url=https://www.bbc.com/news/articles/cpdv649vx7lo |access-date=13 November 2024 |work=[[BBC News]]}}</ref> Articles and posts including images and videos of the events on the day of the attack were censored during the first 24 hours after the attack. This caused tensions on Chinese social media platforms, with people being angered by the delay of details regarding the attack.<ref name="reutersnov12" /> A hashtag mentioning the death toll was censored on [[Weibo]], a Chinese microblogging site.<ref name="BBCrevenge" />

On the morning of 12 November, Weibo only had vague posts indicating that something had happened in Zhuhai.<ref name="AP12" /> Meanwhile, videos spread over [[Twitter|X]] outside Mainland China.<ref name="AP12" /><ref name=":4" /> [[Teacher Li Is Not Your Teacher]] posted a video on X of several people lying on the ground and a woman yelling in pain while a firefighter rendered aid to a victim.<ref name=":0">{{Cite news |last=Hawkins |first=Amy |date=12 November 2024 |title=Dozens killed in China after car driven into sports centre |url=https://www.theguardian.com/world/2024/nov/12/china-car-driven-into-sports-centre-state-media |access-date=12 November 2024 |work=The Guardian |language=en-GB |issn=0261-3077}}</ref> X is banned in China.<ref name="Bloomberg12" />

On 12 November, BBC News journalists including [[Stephen McDonell]] were interrupted and pushed during their live coverage by suspected CCP officials masquerading as locals to prevent coverage.<ref name="BBCshut">{{cite news |last1=McDonell |first1=Stephen |date=12 November 2024 |title=When horror hits China, the first instinct is shut it down |url=https://www.bbc.co.uk/news/articles/cje0z2xppdlo |url-status=live |archive-url=https://web.archive.org/web/20241112214751/https://www.bbc.co.uk/news/articles/cje0z2xppdlo |archive-date=12 November 2024 |access-date=12 November 2024 |work=[[BBC News]] |authorlink=Stephen McDonell}}</ref> A [[TBS Television (Japan)|TBS Television]] reporter tweeted that he was surrounded by people when reporting before being brought to the police, who asked him to delete all his material.<ref>{{cite web |date=13 November 2024 |title=TBS記者、中国で取材中「警察呼ばれ、全て素材削除させられた」広東の車暴走死傷で |trans-title=TBS reporter reporting in China: The police were called and I had to delete all the material due to fatal car accident in Guangdong |url=https://www.sankei.com/article/20241113-C3TJQYQTJFETBG2DXZDBREMACM/ |access-date=13 November 2024 |website=[[Sankei Shimbun]] |language=ja}}</ref> Local officials stayed outside the intensive care units where injured victims were taken after the attack and prevented journalists from speaking with family members.<ref>{{cite news |last=Wang |first=Vivian |date=13 November 2024 |title=After Deadly Car Rampage, Chinese Officials Try to Erase Any Hint of It |url=https://www.nytimes.com/2024/11/13/world/asia/china-car-zhuhai-ramming.html |url-access=subscription |work=[[The New York Times]] |access-date=14 November 2024 |archive-date=14 November 2024 |archive-url=https://web.archive.org/web/20241114023547/https://www.nytimes.com/2024/11/13/world/asia/china-car-zhuhai-ramming.html |url-status=live }}</ref>

A researcher on Chinese censorship from [[Hong Kong Baptist University]] said that the information control on incidents with high death tolls is normal for China. She believed that the reason was to reduce panic and the [[Copycat crime|copycat effect]].<ref name=reutersnov12/>

==See also==
{{Portal|China}}
* [[2023 Guangzhou car attack]]
* [[List of vehicle-ramming attacks]]
* [[2024 Yixing campus massacre]]

==References==
{{reflist}}

==External links==
* [https://www.nytimes.com/video/world/asia/100000009820811/zhuhai-china-car-attack.html Video: Man Kills Dozens in China Car Ramming Attack] – ''[[The New York Times]]'', 12 November 2024.

{{Vehicle-ramming attacks}}
{{Mass violence in China}}

{{DEFAULTSORT:Zhuhai car attack, 2024}}
[[Category:2024 road incidents in Asia]]
[[Category:2020s vehicular rampage]]
[[Category:21st century in Zhuhai|Car attack]]
[[Category:November 2024 events in China]]
[[Category:November 2024 crimes in Asia]]
[[Category:Attacks on buildings and structures in 2024]]
[[Category:Attacks in China in 2024]]
[[Category:Attacks on buildings and structures in China]]
[[Category:Attacks on sports venues]]
[[Category:Disasters in Guangdong]]
[[Category:Stadium disasters]]
[[Category:Vehicular rampage in China]]
[[Category:Censorship in China]]
[[Category:Sina Weibo controversies]]
[[Category:Divorce law]]
[[Category:Marriage, unions and partnerships in China]]
[[Category:Economic history of the People's Republic of China]]

Oxynitride

2024-11-15T08:35:44Z

Leiem: /* List */ link to Phosphoryl_nitride

{{short description|Class of chemical compounds}}
The '''oxynitrides''' are a group of inorganic compounds containing [[oxygen]] and [[nitrogen]] not bound to each other, instead combined with other non-metallic or metallic elements. Some of these are [[oxosalt]]s with oxygen replaced by nitrogen. Some of these compounds do not have a fixed oxygen to nitrogen ratio, but instead form [[Ceramic|ceramics]] with a range of compositions. They are in the class of [[mixed anion compounds]].

Many can be formed by heating an oxide or carbonate with ammonia. The hydrogen can assist by reducing some of the oxygen. With higher temperatures and pressures nitrogen can be heated with a mixed oxide to yield a product.<ref name=fuertes/> Other nitrogen rich compounds that can be heated with oxygen containing material are [[urea]] and [[melamine]]. For example [[urea]] heated with [[ammonium dihydrogen phosphate]] yields a [[phosphorus oxynitride]].

There may not be a definite ratio of nitrogen to oxygen, and also nitrogen and oxygen may be disordered, swapping places at random.

Compared to oxides, the oxynitrides have a smaller band gap.<ref name=":0">{{Cite journal|last1=Tang|first1=Ya|last2=Kato|first2=Kosaku|last3=Oshima|first3=Takayoshi|last4=Mogi|first4=Hiroto|last5=Miyoshi|first5=Akinobu|last6=Fujii|first6=Kotaro|last7=Yanagisawa|first7=Kei-ichi|last8=Kimoto|first8=Koji|last9=Yamakata|first9=Akira|last10=Yashima|first10=Masatomo|last11=Maeda|first11=Kazuhiko|date=2020-07-19|title=Synthesis of Three-Layer Perovskite Oxynitride K 2 Ca 2 Ta 3 O 9 N·2H 2 O and Photocatalytic Activity for H 2 Evolution under Visible Light|journal=Inorganic Chemistry|volume=59|issue=15|language=en|pages=11122–11128|doi=10.1021/acs.inorgchem.0c01607|pmid=32683860|s2cid=220653385|issn=0020-1669}}</ref>

== List ==
{| class="wikitable"
!name
!other name
!formula
!
properties
!reference
|-
|aluminium oxynitride
|ALON
|
|transparent, tough
|-
|Lithium silicon oxynitride
|LiSiON
|
|''Pca''21 Wurtzite structure a=5.1986 b=6.3893 c=4.7398
|<ref name=":1">{{Citation|last1=Brese|first1=Nathaniel E.|title=Crystal chemistry of inorganic nitrides|date=1992|url=http://link.springer.com/10.1007/BFb0036504|work=Complexes, Clusters and Crystal Chemistry|volume=79|pages=307–378|place=Berlin/Heidelberg|publisher=Springer-Verlag|language=en|doi=10.1007/bfb0036504|isbn=978-3-540-55095-2|access-date=2020-11-11|last2=O'Keeffe|first2=Michael}}</ref>
|-
|
|SiAlON
|SiAlNO (Li,Mg,Y,Le,Ce,Eu)
|
|
|-
|Silicon oxynitride
|
|
|
|-
|sodium silicon oxynitride
|
|NaSiON
|white Wurtzite structure
|<ref name=":1" />
|-
|Sinoite
|
|Si2N2O
|
mineral
|
|-
|
|
|Li14Cr2N8O
|P{{overbar|3}} a=5.799 c=8.263
|<ref name=":1" />
|-
|
|
|NaGeON
|white Wurtzite structure
|<ref name=":1" />
|-
|potassium germanium oxynitride
|
|KGeON
|yellow Wurtzite structure a=5.7376 b=8.0535 c=5.2173
|<ref name=":1" />
|-
|
|
|(Si,Ge)2N2O
|
|<ref>{{Cite journal|last1=Kang|first1=Lei|last2=He|first2=Gang|last3=Zhang|first3=Xinyuan|last4=Li|first4=Jiangtao|last5=Lin|first5=Zheshuai|last6=Huang|first6=Bing|date=2021-05-17|title=Alloy Engineering of a Polar (Si,Ge) 2 N 2 O System for Controllable Second Harmonic Performance|url=https://pubs.acs.org/doi/10.1021/acs.inorgchem.1c00590|journal=Inorganic Chemistry|language=en|volume=60|issue=10|pages=7381–7388|doi=10.1021/acs.inorgchem.1c00590|pmid=33905663|issn=0020-1669|arxiv=2009.06932|s2cid=231925656}}</ref>
|-
|
|
|CaTaO2N
|perovskite
|<ref name="fuertes">{{cite journal |last1=Fuertes |first1=Amparo |title=Chemistry and applications of oxynitride perovskites |journal=Journal of Materials Chemistry |date=2012 |volume=22 |issue=8 |pages=3293 |doi=10.1039/C2JM13182J}}</ref>
|-
|
|
|SrTaO2N
|perovskite
|<ref name="fuertes" />
|-
|
|
|BaTaO2N
|perovskite
|<ref name="fuertes" />
|-
|
|
|CaNbO2N
|perovskite
|<ref name="fuertes" />
|-
|
|
|SrNbO2N
|perovskite
|<ref name="fuertes" />
|-
|
|
|Sr2NbO3N
|
|<ref name="fuertes" />
|-
|strontium gallium oxynitride
|
|Sr4GaN3O
|red ''Pbca'' a = 7.4002 b = 24.3378 c = 7.4038Å'', Z = 8''
|<ref>{{Cite journal|last1=Mallinson|first1=Phillip M.|last2=Gál|first2=Zoltán A.|last3=Clarke|first3=Simon J.|date=January 2006|title=Two New Structurally Related Strontium Gallium Nitrides: Sr 4 GaN 3 O and Sr 4 GaN 3 (CN 2 )|url=https://pubs.acs.org/doi/10.1021/ic051542q|journal=Inorganic Chemistry|language=en|volume=45|issue=1|pages=419–423|doi=10.1021/ic051542q|pmid=16390084|issn=0020-1669}}</ref>
|-
|
|
|Sr3Nb2O5N2
|
|<ref name="fuertes" />
|-
|
|
|In32ON17F43
|''Ia''{{overbar|3}} a=10.536 fluorite structure
|
|-
|
|
|BaNbO2N
|perovskite
|<ref name="fuertes" />
|-
|
|
|LaTaON2
|
|<ref name="fuertes" />
|-
|
|
|LnTiO2N
|
|<ref name="fuertes" />
|-
|
|
|LnTaO2N
|
|<ref name="fuertes" />
|-
|
|
|EuTaO2N
|
|<ref name="fuertes" />
|-
|
|
|EuNbO2N
|
|<ref name="fuertes" />
|-
|
|
|LnNbO2N
|
|<ref name="fuertes" />
|-
|
|
|LnVO2N
|
|<ref name="fuertes" />
|-
|
|
|CaTiO2N
|
|<ref name="fuertes" />
|-
|
|
|CaZrO2N
|
|<ref name="fuertes" />
|-
|
|
|LaZrO2N
|
|<ref name="fuertes" />
|-
|
|
|EuWON2
|
|<ref name="fuertes" />
|-
|
|
|Ln2AlO3N
|
|<ref name="fuertes" />
|-
|[[Phosphoryl nitride]]
|PNO
|
|
α-quartz, β-cristobalite, or moganite structure
|-
|Titanium nickel oxynitride
|
|NiTiNO
|
|-
|Chromium oxynitride
|
|Cr(N,O)
|
|-
|galloaluminophosphate oxynitride
|AlGaPON
|
|
|<ref>{{cite journal|last1=Lee|first1=Eunha|last2=Kim|first2=Taeho|last3=Benayad|first3=Anass|last4=Hur|first4=Jihyun|last5=Park|first5=Gyeong-Su|last6=Jeon|first6=Sanghun|date=5 April 2016|title=High mobility and high stability glassy metal-oxynitride materials and devices|journal=Scientific Reports|language=en|volume=6|issue=1|page=23940|doi=10.1038/srep23940|pmid=27044371|pmc=4820723|bibcode=2016NatSR...623940L|issn=2045-2322|doi-access=free}}</ref>
|-
|zinc oxynitride
|ZnON
|
|
|
|-
|Titanium oxynitride
|
|TiOxNy
|
|<ref>{{cite journal|last1=Braic|first1=Laurentiu|last2=Vasilantonakis|first2=Nikolaos|last3=Mihai|first3=Andrei|last4=Villar Garcia|first4=Ignacio Jose|last5=Fearn|first5=Sarah|last6=Zou|first6=Bin|last7=Alford|first7=Neil McN.|last8=Doiron|first8=Brock|last9=Oulton|first9=Rupert F.|last10=Maier|first10=Stefan A.|last11=Zayats|first11=Anatoly V.|date=24 August 2017|title=Titanium Oxynitride Thin Films with Tunable Double Epsilon-Near-Zero Behavior for Nanophotonic Applications|journal=ACS Applied Materials & Interfaces|volume=9|issue=35|pages=29857–29862|doi=10.1021/acsami.7b07660|last12=Petrov|first12=Peter K.|pmid=28820932|hdl=10044/1/52727|s2cid=206458627|hdl-access=free}}</ref>
|-
|
|
|K2Ca2Ta3O9N·2H2O
|perovskite
|<ref name=":0" />
|-
|
|
|K2LaTa2O6N·1.6H2O
|
|<ref name=":0" />
|}

==References==
{{Reflist}}

{{nitrides}}
{{oxides}}

[[Category:Oxygen compounds]]
[[Category:Nitrides]]

Protactinyl nitrate

2024-11-15T08:03:16Z

Leiem: CAS RN 13973-99-4 for PaO(NO3)3. (Note: 14887-32-2 for the similar compd "Pa(OH)2(NO3)3")

{{Chembox

| ImageFile =
| ImageSize =
| ImageAlt =

| IUPACName =
| OtherNames = {{Unbulleted list
| Protactinium(V) oxynitrate
}}

| Section1 = {{Chembox Identifiers
| CASNo = 13973-99-4
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem =
| StdInChI=1S/3NO3.O.Pa/c3*2-1(3)4;;/q3*-1;;+3
| StdInChIKey=HPGAUFDFQPEWQU-UHFFFAOYSA-N
| SMILES = [Pa](O[N+]([O-])=O)(O[N+]([O-])=O)(O[N+]([O-])=O)=O
}}
| Section2 = {{Chembox Properties
| Formula = PaO(NO3)3
| MolarMass = 433.05 g/mol
| Appearance = White solid<ref name="quin">{{cite journal |author1=D. Brown |author2=P. J. Jones |title=Quinquevalent protactinium, niobium, and tantalum nitrates and nitrato-complexes |journal=Journal of the Chemical Society A: Inorganic, Physical, Theoretical |date=1966 |pages=733–737 |doi=10.1039/J19660000733 |language=en}}</ref>
| Density =
| MeltingPtC = 400
| MeltingPt_notes= (decomposition)
| BoilingPt =
| Solubility = Hydrolysis<ref name="quin" />
| SolubleOther = Soluble in fuming [[nitric acid]]<ref name="quin" />
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
| Section9 = {{Chembox Related
| OtherAnions =
| OtherCations = [[Uranyl nitrate]]
| OtherFunction =
| OtherFunction_label =
| OtherCompounds =
}}
}}
'''Protactinyl nitrate''', '''protactinium(V) oxynitrate''', or erroneously known as protactinium nitrate, is a radioactive chemical compound with the formula PaO(NO3)3·''x''H2O (1.5 ≤ ''x'' ≤ 4). It is a white solid that readily hydrolyzes to [[protactinium(V) oxide]] in moist air. This compound is a common commercial source of protactinium.<ref name="prep">{{cite journal |author1=R. Grossmann |author2=H.J. Maier |author3=J. Szerypo |author4=H.U. Friebel |title=Preparation of 231Pa targets |journal=Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment |date=2008 |volume=590 |issue=1–3 |pages=122–125 |doi=10.1016/j.nima.2008.02.084 |language=en}}</ref>

==Preparation and decomposition==
Protactinyl nitrate was first prepared in 1966 by reacting [[protactinium(V) chloride]] or [[protactinium(V) bromide]] with fuming [[nitric acid]]. Lower concentrations of nitric acid cannot be used, due to the hydrolysis of the compound.<ref name="quin" />

Protactinyl nitrate decomposes at 400 °C to [[protactinium(V) oxide]].<ref name="prep" /><ref name="quin" />

==References==
{{reflist}}

{{Protactinium compounds}}
{{Nitrates}}

[[Category:Protactinium compounds]]
[[Category:Nitrates]]

Talk:Dibromo neopentyl glycol diglycidyl ether

2024-11-15T07:14:11Z

Leiem: /* New article */

== New article ==

I think this article is needed. Part of a series on glycidyl ethers. [[User:GRALISTAIR|GRALISTAIR]] ([[User talk:GRALISTAIR|talk]]) 19:04, 14 November 2024 (UTC)
: {{CAS|31452-80-9}} is not a correct CAS RN for this substance. The CAS RN for this substance is not registered yet. However, {{CAS|29953-15-9}} (SMILES: BrCC(CBr)(COCC1OC1)COCC2OC2) also called "dibromoneopentyl glycol diglycidyl ether" has the similar structure. --[[User:Leiem|Leiem]] ([[User talk:Leiem|talk]]) 07:14, 15 November 2024 (UTC)

ADA (buffer)

2024-11-15T06:54:15Z

Leiem: removed Category:Tricarboxylic acids; added Category:Dicarboxylic acids using HotCat

{{refimprove|date=November 2024}}
{{chembox
| Name = ADA
| ImageFile = ADA (buffer).png
| ImageName = Chemical structure of ADA
| SystematicName = 2,2′-[(2-amino-2-oxoethyl)azanediyl]diacetic acid
| OtherNames = ADA, N-(2-acetamido)iminodiacetic acid, N-(carbamoylmethyl)iminodiacetic acid
|Section1={{Chembox Identifiers
| InChI = 1S/C6H10N2O5/c7-4(9)1-8(2-5(10)11)3-6(12)13/h1-3H2,(H2,7,9)(H,10,11)(H,12,13)
| InChIKey = QZTKDVCDBIDYMD-UHFFFAOYSA-N
| SMILES = C(C(=O)N)N(CC(=O)O)CC(=O)O
| CASNo = 26239-55-4
| ChEBI = 43960
| DrugBank = DB02810
| ChemSpiderID = 105243
| UNII = 5C4R3O704E
| EC_number = 247-530-0
| PubChem = 117765
}}
| Section2 = {{Chembox Properties
| C=6 | H=10 | N=2 | O=5
| MolarMass = 190.155 g/mol
| pKa = 6.6
}}
| Section3 = {{Chembox Hazards
| MainHazards = Irritant
| FlashPt = Non-flammable
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|319|335}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
}}
}}

'''ADA''' is a [[zwitterionic]] organic chemical [[buffering agent]]; one of [[Good's buffers]]. It has a useful [[pH]] range of 6.0-7.2 in the physiological range, making it useful for [[cell culture]] work. It has a [[pKa]] of 6.6 with ΔpKa/°C of -0.011 and is most often prepared in 1 M [[NaOH]] where it has a solubility of 160 mg/mL.

ADA has been used in protein-free media for chicken embryo fibroblasts, as a [[chelating agent]] for H+, Ca2+, and Mg2+, and for [[isoelectric focusing]] in immobilized pH gradients. Its effects on dog kidney [[Na+/K+-ATPase|Na+/K+-ATPase]] and rat brain [[GABA receptor]]s have also been studied. ADA does, however, alter coloring in [[bicinchoninic acid assay]]s.<ref>{{cite web| title=ADA| website=Sigma-Aldrich| url=http://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/a9883pis.pdf}}</ref>

==References==
{{reflist}}

[[Category:Zwitterions]]
[[Category:Amines]]
[[Category:Dicarboxylic acids]]
[[Category:Buffer solutions]]

Diphenylphosphite

2024-11-11T08:44:50Z

Leiem: added a space between phenyl and phosphite

{{Chembox
| ImageFile = Diphenylphosphite.png
| ImageSize = 132
| PIN = Diphenyl phosphonate
| OtherNames = Phosphonic acid, diphenyl ester
|Section1={{Chembox Identifiers
| CASNo = 4712-55-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5144JS6XUM
|PubChem = 426896
| ChemSpiderID = 377689
| ChEMBL = 132913
| InChI = 1S/C12H11O3P/c13-16(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10,13H
| InChIKey = FYOYCZHNDCCGCE-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)OP(O)OC2=CC=CC=C2
}}
|Section2={{Chembox Properties
| C=12|H=11|O=3|P=1
| Appearance = colorless liquid
| Density = 1.2268 g/cm3
| MeltingPtC = 12
}}
}}

'''Diphenyl phosphite''' is a [[phosphite ester|diorganophosphite]] with the formula (C6H5O)2P(O)H. The molecule is [[tetrahedral molecular geometry|tetrahedral]]. It is a colorless viscous liquid. The compounds can be prepared by treating [[phosphorus trichloride]] with phenol. Many analogues can be prepared similarly. One illustrative reaction, diphenylphosphite, aldehydes, and amines react to afford [[aminophosphonate]]s ([[Kabachnik–Fields reaction]]).<ref>{{cite journal|title=An Extremely Efficient Three-Component Reaction of Aldehydes/Ketones, Amines, and Phosphites Kabachnik-Fields reaction for the Synthesis of α-Aminophosphonates Catalyzed by Magnesium Perchlorate|author1=Bhagat, Srikant |author2=Chakraborti, Asit K. |journal=Journal of Organic Chemistry|year=2007|volume=72|issue=4 |pages=1263–1270|doi=10.1021/jo062140i|pmid=17253748 }}</ref>

==See also==
*[[Dimethylphosphite]]
*[[Diethylphosphite]]
*[[Diisopropylphosphite]]

==References==
<references />

[[Category:Organophosphites]]

Diisopropylphosphite

2024-11-11T08:44:21Z

Leiem: added a space between isopropyl and phosphite

{{Chembox
| ImageFile = Diisopropylphosphite.png
| ImageSize = 132
| ImageAlt =
| PIN = Di(propan-2-yl) phosphonate
| OtherNames = Phosphonic acid, diisopropyl ester, diisopropyl phosphonate
|Section1={{Chembox Identifiers
| CASNo = 1809-20-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 676G4RQ6ND
| PubChem = 558181
| ChemSpiderID = 485223
| EC_number = 217-317-7
| InChI=1S/C6H15O3P/c1-5(2)8-10(7)9-6(3)4/h5-7H,1-4H3
| InChIKey = NFORZJQPTUSMRL-UHFFFAOYSA-N
| SMILES = CC(C)OP(O)OC(C)C }}
|Section2={{Chembox Properties
| C=6|H=15|O=3|P=1
| MolarMass =
| Appearance = colorless liquid
| Density =
| MeltingPtC =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}

'''Diisopropyl phosphite''' is an [[organophosphorus compound]] with the formula (i-PrO)2P(O)H (i-Pr = CH(CH3)2). The molecule is [[tetrahedral molecular geometry|tetrahedral]]. It is a colorless viscous liquid. The compounds can be prepared by treating [[phosphorus trichloride]] with [[isopropanol]].<ref name='CSSP488'>{{cite journal|last = Pedrosa|first = Leandro|year = 2011|url = http://cssp.chemspider.com/488|title = Esterification of Phosphorus Trichloride with Alcohols; Diisopropyl phosphonate|journal = ChemSpider Synthetic Pages|pages=488|doi = 10.1039/SP488|publisher = Royal Society of Chemistry|doi-access = free}}</ref>

==References==
<references />

[[Category:Organophosphites]]

Zirconium(IV) acetate

2024-11-06T07:37:48Z

Leiem: remove misinserted texts

{{chembox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| ImageFile = CSD CIF KAVRUX.jpg
| ImageSize =
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| Abbreviations =
| CASNo =4229-34-9
| ChemSpiderID =
| EINECS =
| PubChem =
| StdInChI=1S/12C2H4O2.4H2O.4O.6Zr/c12*1-2(3)4;;;;;;;;;;;;;;/h12*1H3,(H,3,4);4*1H2;;;;;;;;;;/q;;;;;;;;;;;;;;;;4*-2;6*+4/p-16
| StdInChIKey = RGWBNEKRIQDQRP-UHFFFAOYSA-A
| SMILES = [Zr+4].[Zr+4].[Zr+4].[Zr+4].[Zr+4].[Zr+4].[OH-].[OH-].[OH-].[OH-].[O-2].[O-2].[O-2].[O-2].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-]
}}
|Section2={{Chembox Properties
| Zr=6|O=32|H=40|C=24
| MolarMass =
| Appearance = white solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = soluble
}}
|Section3={{Chembox Structure
| CrystalStruct =
| Coordination =
| MolShape = }}
|Section4={{Chembox Thermochemistry
| DeltaHf =
| DeltaHc =
| Entropy =
| HeatCapacity = }}
|Section7={{Chembox Hazards
| ExternalSDS =
| EUClass =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| RPhrases =
| SPhrases =
| RSPhrases =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds = [[zirconium dioxide]], [[zirconium(IV) chloride]]}}
}}

'''Zirconium acetate''' usually refers to the [[chemical formula]] {{chem2|Zr6O4(OH)4(O2CCH3)12}}. It forms by the reaction of zirconyl chloride and acetate. Claims of {{chem2|Zr(O2CCH3)4}}<ref>Pavlov, V. L.; Lysenko, Yu. A.; Kalinichenko, A. A. Synthesis and properties of zirconium tetraacetate.{{in lang|ru}} ''Zhurnal Neorganicheskoi Khimii'', 1972. 17(12). ISSN 0044-457X</ref> have been superseded by experiments using [[X-ray crystallography]].<ref>{{cite journal |doi=10.1021/acs.inorgchem.6b01624 |title=Solution Species and Crystal Structure of Zr(IV) Acetate |date=2017 |last1=Hennig |first1=Christoph |last2=Weiss |first2=Stephan |last3=Kraus |first3=Werner |last4=Kretzschmar |first4=Jerome |last5=Scheinost |first5=Andreas C. |journal=Inorganic Chemistry |volume=56 |issue=5 |pages=2473–2480 |pmid=28199091 }}</ref>

The species {{chem2|Zr6O4(OH)4(O2CCH3)12}} is a common precursor to [[metal-organic framework]]s (MOFs).<ref>{{cite journal |doi=10.1021/ja8057953 |title=A New Zirconium Inorganic Building Brick Forming Metal Organic Frameworks with Exceptional Stability |date=2008 |last1=Cavka |first1=Jasmina Hafizovic |last2=Jakobsen |first2=Søren |last3=Olsbye |first3=Unni |last4=Guillou |first4=Nathalie |last5=Lamberti |first5=Carlo |last6=Bordiga |first6=Silvia |last7=Lillerud |first7=Karl Petter |journal=Journal of the American Chemical Society |volume=130 |issue=42 |pages=13850–13851 |pmid=18817383 }}</ref>

==References==
{{reflist}}

{{Zirconium compounds}}
{{Acetates}}

[[Category:Zirconium(IV) compounds]]
[[Category:Acetates]]

Cobalt(II) chlorate

2024-11-06T07:00:26Z

Leiem: mp

{{Chembox
| Watchedfields = changed
| verifiedrevid = 414081638
| ImageFile =
| ImageSize =
| IUPACName =
| SystematicName =
| OtherNames = cobaltous chlorate
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14688171
| InChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| InChIKey = IQYVXTLKMOTJKI-NUQVWONBAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| InChIKey1 = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| CASNo = 80546-49-2
| CASNo_Ref = {{Cascite|correct|CAS}}
| EINECS =
| PubChem = 20034997
| SMILES = [Co+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O
| RTECS =
| MeSHName =
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
}}
|Section2={{Chembox Properties
| Formula = Co(ClO3)2
| MolarMass = 225.9 g/mol
| Appearance = deliquescent pink crystals
| Density =
| MeltingPt = 50 °C (hexahydrate)<ref>{{cite book|url=https://books.google.com/books?id=TrdCAAAAIAAJ&pg=PA225|author=rthur Messinger Comey|title=A Dictionary of Chemical Solubilities: Inorganic|page=225|year=1921|publisher=Macmillan Company}}</ref>
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = soluble in water
| SolubleOther =
| Solvent =
| LogP =
| VaporPressure =
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa =
| pKb = }}
|Section3={{Chembox Structure
| CrystalStruct =
| Coordination =
| MolShape = }}
|Section4={{Chembox Thermochemistry
| DeltaHf =
| DeltaHc =
| Entropy =
| HeatCapacity = }}
|Section5={{Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_US = }}
|Section6={{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor = }}
|Section7={{Chembox Hazards
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations = [[nickel chlorate]]
[[iron chlorate]]
| OtherFunction =
| OtherFunction_label =
| OtherCompounds =
}}
}}

'''Cobalt(II) chlorate''' is a [[chemical compound]] with the formula Co(ClO3)2. It is an [[oxidant]], as are all chlorates.

== Preparation ==

Cobalt(II) chlorate is formed by a double displacement reaction between [[cobalt(II) sulfate]] and [[barium chlorate]], [[barium sulfate]] precipitates and cobalt chlorate can be crystallized out of the filtrate:<ref>Xie, Gaoyang; et al. Series of Inorganic Chemistry. Volume IX - Manganese group, iron group and platinum group. Science Press, 1996. pp 303. Cobalt halates and perhalates. {{isbn|9787030305459}} (in Chinese)</ref>

: CoSO4 + Ba(ClO3)2 → BaSO4 + Co(ClO3)2

It is also possible to make it by the reaction of any chlorate with a cobalt(II) salt, however the pure product is harder to separate.

==References==
<references />

{{Cobalt compounds}}
{{Chlorates}}

[[Category:Cobalt(II) compounds]]
[[Category:Chlorates]]
[[Category:Oxidizing agents]]

{{inorganic-compound-stub}}

Cobalt(II) chlorate

2024-11-06T06:51:32Z

Leiem: Translation

{{Chembox
| Watchedfields = changed
| verifiedrevid = 414081638
| ImageFile =
| ImageSize =
| IUPACName =
| SystematicName =
| OtherNames = cobaltous chlorate
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14688171
| InChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| InChIKey = IQYVXTLKMOTJKI-NUQVWONBAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| InChIKey1 = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| CASNo = 80546-49-2
| CASNo_Ref = {{Cascite|correct|CAS}}
| EINECS =
| PubChem = 20034997
| SMILES = [Co+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O
| RTECS =
| MeSHName =
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
}}
|Section2={{Chembox Properties
| Formula = Co(ClO3)2
| MolarMass = 225.9 g/mol
| Appearance = pink crystals
| Density =
| MeltingPt =
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = soluble in water
| SolubleOther =
| Solvent =
| LogP =
| VaporPressure =
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa =
| pKb = }}
|Section3={{Chembox Structure
| CrystalStruct =
| Coordination =
| MolShape = }}
|Section4={{Chembox Thermochemistry
| DeltaHf =
| DeltaHc =
| Entropy =
| HeatCapacity = }}
|Section5={{Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_US = }}
|Section6={{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor = }}
|Section7={{Chembox Hazards
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations = [[nickel chlorate]]
[[iron chlorate]]
| OtherFunction =
| OtherFunction_label =
| OtherCompounds =
}}
}}

'''Cobalt(II) chlorate''' is a [[chemical compound]] with the formula Co(ClO3)2. It is an [[oxidant]], as are all chlorates.

== Preparation ==

Cobalt(II) chlorate is formed by a double displacement reaction between [[cobalt(II) sulfate]] and [[barium chlorate]], [[barium sulfate]] precipitates and cobalt chlorate can be crystallized out of the filtrate:<ref>Xie, Gaoyang; et al. Series of Inorganic Chemistry. Volume IX - Manganese group, iron group and platinum group. Science Press, 1996. pp 303. Cobalt halates and perhalates. {{isbn|9787030305459}} (in Chinese)</ref>

: CoSO4 + Ba(ClO3)2 → BaSO4 + Co(ClO3)2

It is also possible to make it by the reaction of any chlorate with a cobalt(II) salt, however the pure product is harder to separate.

==References==
<references />

{{Cobalt compounds}}
{{Chlorates}}

[[Category:Cobalt(II) compounds]]
[[Category:Chlorates]]
[[Category:Oxidizing agents]]

{{inorganic-compound-stub}}

Cobalt(II) chlorate

2024-11-06T06:47:37Z

Leiem:

{{Chembox
| Watchedfields = changed
| verifiedrevid = 414081638
| ImageFile =
| ImageSize =
| IUPACName =
| SystematicName =
| OtherNames = cobaltous chlorate
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14688171
| InChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| InChIKey = IQYVXTLKMOTJKI-NUQVWONBAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2ClHO3.Co/c2*2-1(3)4;/h2*(H,2,3,4);/q;;+2/p-2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| InChIKey1 = IQYVXTLKMOTJKI-UHFFFAOYSA-L
| CASNo = 80546-49-2
| CASNo_Ref = {{Cascite|correct|CAS}}
| EINECS =
| PubChem = 20034997
| SMILES = [Co+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O
| RTECS =
| MeSHName =
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
}}
|Section2={{Chembox Properties
| Formula = Co(ClO3)2
| MolarMass = 225.9 g/mol
| Appearance = pink crystals
| Density =
| MeltingPt =
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = soluble in water
| SolubleOther =
| Solvent =
| LogP =
| VaporPressure =
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa =
| pKb = }}
|Section3={{Chembox Structure
| CrystalStruct =
| Coordination =
| MolShape = }}
|Section4={{Chembox Thermochemistry
| DeltaHf =
| DeltaHc =
| Entropy =
| HeatCapacity = }}
|Section5={{Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_US = }}
|Section6={{Chembox Explosive
| ShockSens =
| FrictionSens =
| DetonationV =
| REFactor = }}
|Section7={{Chembox Hazards
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
|Section8={{Chembox Related
| OtherAnions =
| OtherCations = [[nickel chlorate]]
[[iron chlorate]]
| OtherFunction =
| OtherFunction_label =
| OtherCompounds =
}}
}}

'''Cobalt(II) chlorate''' is a [[chemical compound]] with the formula Co(ClO3)2. It is an [[oxidant]], as are all chlorates.

== Preparation ==

Cobalt(II) chlorate is formed by a double displacement reaction between [[cobalt(II) sulfate]] and [[barium chlorate]], [[barium sulfate]] precipitates and cobalt chlorate can be crystallized out of the filtrate:<ref>《无机化学丛书》.第九卷锰分族铁系铂系. P303. 卤酸钴和高卤酸钴</ref>

: CoSO4 + Ba(ClO3)2 → BaSO4 + Co(ClO3)2

It is also possible to make it by the reaction of any chlorate with a cobalt(II) salt, however the pure product is harder to separate.

==References==
<references />

{{Cobalt compounds}}
{{Chlorates}}

[[Category:Cobalt(II) compounds]]
[[Category:Chlorates]]
[[Category:Oxidizing agents]]

{{inorganic-compound-stub}}

Dipropalin

2024-11-04T04:50:14Z

Leiem: {{Unreliable source?}}

{{Short description|Weed control herbicide}}
{{confuse|Dipropylin}}
{{Chembox
| Reference =
| ImageFile =
| PIN = 4-methyl-2,6-dinitro-N,N-dipropylaniline
| OtherNames = {{ubl|L-35355|2,6-Dinitro-N,N-dipropyl-p-toluidine| 4-methyl-2,6-dinitro-N,N-dipropylbenzenamine|地乐灵 (Geleling)}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 15171
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1918-08-7
| PubChem = 15966
| UNII = 389074G62J
| StdInChI=1S/C13H19N3O4/c1-4-6-14(7-5-2)13-11(15(17)18)8-10(3)9-12(13)16(19)20/h8-9H,4-7H2,1-3H3
| StdInChIKey = UDVZOMAEGATTSE-UHFFFAOYSA-N
| SMILES = CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C)[N+](=O)[O-]
}}
|Section2={{Chembox Properties
| C=13|H=19|N=3|O=4
| Appearance = Yellow crystals<ref name = "database"/>
| Odour =
| Density =
| MeltingPtC = 42
| MeltingPt_notes = {{cn|date=November 2024}}
| BoilingPtC = 118
| BoilingPt_notes =
| Solubility = 0.3 g/L{{cn|date=November 2024}}
| Solvent1 = acetone
| Solubility1 =
| VaporPressure =
}}
|Section3={{Chembox Hazards
| MainHazards =
| HPhrases =
| GHS_ref=
| GHSPictograms =
| GHSSignalWord =
| PPhrases =
| LD50 =
| LC50 = Over 3600 mg.kg (rat, oral)<ref name = "database"/>
| FlashPtC =
| AutoignitionPtF =
}}
}}

'''Dipropalin''' is a preëmergent [[dinitroaniline]] [[herbicide]]. It is not now commercially used in western countries,<ref name="database">{{Cite journal |last1=Lewis |first1=Kathleen A. |last2=Tzilivakis |first2=John |last3=Warner |first3=Douglas J. |last4=Green |first4=Andrew |date=2016-05-18 |title=An international database for pesticide risk assessments and management |journal=Human and Ecological Risk Assessment: An International Journal |language=en |volume=22 |issue=4 |pages=1050–1064 |doi=10.1080/10807039.2015.1133242 |bibcode=2016HERA...22.1050L |hdl=2299/17565 |issn=1080-7039}}</ref> but may be available in China.<ref>{{cite web |title=地乐灵详细信息_百度知道 |url=https://zhidao.baidu.com/question/2022978001017111228.html |website=zhidao.baidu.com}}</ref>{{Unreliable source?}} It has low acute toxicity.<ref name = "database"/> It is used on turf.<ref name = "database"/> Tests in the 1960s in the USA evaluated its performance as a [[trifluralin]] analog, where it scored the highest pre-emergent effectiveness amongst methyl-group analogs, though losing to several trifluoromethyls, such as trifluralin itself. Dipropalin's [[methyl]] group does see increased post-emergent activity, but no trifluralin analog was effective in this regard.<ref>{{cite journal |last1=Gentner |first1=W. A. |title=Herbicidal Properties of Trifluralin Analogs |journal=Weeds |date=1966 |volume=14 |issue=2 |pages=176–178 |doi=10.2307/4040959|jstor=4040959 }}</ref>

== References ==
{{reflist}}

== Links ==
* {{PPDB|2885}}

{{Herbicides}}

[[Category:Preemergent herbicides]]
[[Category:Nitrotoluene derivatives]]
[[Category:Anilines]]
[[Category:Herbicides]]

Cyanoacetamide

2024-10-31T02:31:45Z

Leiem: pKa

{{chembox
|Name = 2-Cyanoacetamide
|ImageFile = Cyanoacetamide.svg
|ImageSize = 150px
|PIN = 2-Cyanoacetamide
|OtherNames = Malonamide nitrile 3-Nitrilopropionamide
|Section1={{Chembox Identifiers
|ChemSpiderID = 7610
|PubChem = 7898
|SMILES = N#CCC(=O)N
|StdInChI = 1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
|StdInChIKey = DGJMPUGMZIKDRO-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 107-91-5
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = YBK38G2YXH
|EINECS = 203-531-8}}
|Section2={{Chembox Properties
|C=3 | H=4 | N=2 | O=1
|Density = 1.163 g/cm3
|MeltingPtC = 119 to 121
|BoilingPtC = 351.2
|pKa = ca. 11<ref>{{cite book|url=https://books.google.com/books?id=UVd-DAAAQBAJ&pg=PA28|title=Organic Functional Group Analysis: Theory and Development|author=George H. Schenk|publisher=Elsevier|date=Jun 23, 2016|isbn=9781483136073}}</ref> 13.24<ref>{{cite journal|author=Jay Sung; Si-Ying Hsu; Tzu-Hua Wang; Amanda Pan; Andrew Yeh|title=Kinetic studies of the reactions of pentacyanonitrosylferrate(2−) with ligands containing acidic methylene groups|journal=Inorganica Chimica Acta|volume=359|issue=12|year=2006|pages=3888-3894|doi=10.1016/j.ica.2006.04.042}}</ref>
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{GHS07}}
|GHSSignalWord = Warning
|HPhrases = {{H-phrases|302|315|319|335}}
|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
}}
}}

'''2-Cyanoacetamide''' is an [[organic compound]]. It is an [[acetic]] [[amide]] with a [[nitrile]] [[functional group]].

==Uses==
Cyanoacetamide is used in [[Fluorescence spectroscopy|spectrofluorimetric methods]] to determine the activity of [[Antihistamine#H1-antihistamines|antihistamine H1]] [[receptor antagonist]]ic drugs such as [[ebastine]], [[cetirizine|cetirizine dihydrochloride]] and [[fexofenadine|fexofenadine hydrochloride]].<ref>{{cite journal|last1=Ibrahim|first1=F.|last2=Sharaf El-Din|first2=M. K.|last3=Eid|first3=M.|last4=Wahba|first4=M. E. K.|title=Spectrofluorimetric Determination Of Some H1 Receptor Antagonist Drugs In Pharmaceutical Formulations And Biological Fluids|journal=International Journal of Pharmaceutical Sciences and Research|date=2011|volume=21|issue=8|pages=2056–2072|doi=10.13040/IJPSR.0975-8232.2(8).2056-72|doi-access=free}}</ref>

==Preparation==
2-Cyanoacetamide is prepared from [[chloroacetic acid]] via [[Kolbe nitrile synthesis]]<ref>{{cite journal|last1=Inglis|first1=J. K. H.|title=Ethyl Cyanoacetate|journal=Organic Syntheses|date=1928|volume=8|page=74|doi=10.15227/orgsyn.008.0074}}</ref> followed by [[Fischer esterification]] and [[ester]] [[aminolysis]].<ref>{{cite journal|last1=Corson|first1=B. B.|last2=Scott|first2=R. W.|last3=Vose|first3=C. E.|title=Cyanoacetamide|journal=Organic Syntheses|date=1941|volume=1|page=179|doi=10.15227/orgsyn.009.0036}}</ref>

==See also==
*[[Chloroacetamide]]
*[[Ethyl chloroacetate]]

==References==
{{Reflist}}

{{organic-compound-stub}}
[[Category:Acetamides]]
[[Category:Nitriles]]

Cyanoacetamide

2024-10-29T13:20:22Z

Leiem: pKa

{{chembox
|Name = 2-Cyanoacetamide
|ImageFile = Cyanoacetamide.svg
|ImageSize = 150px
|PIN = 2-Cyanoacetamide
|OtherNames = Malonamide nitrile 3-Nitrilopropionamide
|Section1={{Chembox Identifiers
|ChemSpiderID = 7610
|PubChem = 7898
|SMILES = N#CCC(=O)N
|StdInChI = 1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
|StdInChIKey = DGJMPUGMZIKDRO-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 107-91-5
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = YBK38G2YXH
|EINECS = 203-531-8}}
|Section2={{Chembox Properties
|C=3 | H=4 | N=2 | O=1
|Density = 1.163 g/cm3
|MeltingPtC = 119 to 121
|BoilingPtC = 351.2
|pKa = ca. 11<ref>{{cite book|url=https://books.google.com/books?id=UVd-DAAAQBAJ&pg=PA28|title=Organic Functional Group Analysis: Theory and Development|author=George H. Schenk|publisher=Elsevier|date=Jun 23, 2016|isbn=9781483136073}}</ref>
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{GHS07}}
|GHSSignalWord = Warning
|HPhrases = {{H-phrases|302|315|319|335}}
|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}}
}}
}}

'''2-Cyanoacetamide''' is an [[organic compound]]. It is an [[acetic]] [[amide]] with a [[nitrile]] [[functional group]].

==Uses==
Cyanoacetamide is used in [[Fluorescence spectroscopy|spectrofluorimetric methods]] to determine the activity of [[Antihistamine#H1-antihistamines|antihistamine H1]] [[receptor antagonist]]ic drugs such as [[ebastine]], [[cetirizine|cetirizine dihydrochloride]] and [[fexofenadine|fexofenadine hydrochloride]].<ref>{{cite journal|last1=Ibrahim|first1=F.|last2=Sharaf El-Din|first2=M. K.|last3=Eid|first3=M.|last4=Wahba|first4=M. E. K.|title=Spectrofluorimetric Determination Of Some H1 Receptor Antagonist Drugs In Pharmaceutical Formulations And Biological Fluids|journal=International Journal of Pharmaceutical Sciences and Research|date=2011|volume=21|issue=8|pages=2056–2072|doi=10.13040/IJPSR.0975-8232.2(8).2056-72|doi-access=free}}</ref>

==Preparation==
2-Cyanoacetamide is prepared from [[chloroacetic acid]] via [[Kolbe nitrile synthesis]]<ref>{{cite journal|last1=Inglis|first1=J. K. H.|title=Ethyl Cyanoacetate|journal=Organic Syntheses|date=1928|volume=8|page=74|doi=10.15227/orgsyn.008.0074}}</ref> followed by [[Fischer esterification]] and [[ester]] [[aminolysis]].<ref>{{cite journal|last1=Corson|first1=B. B.|last2=Scott|first2=R. W.|last3=Vose|first3=C. E.|title=Cyanoacetamide|journal=Organic Syntheses|date=1941|volume=1|page=179|doi=10.15227/orgsyn.009.0036}}</ref>

==See also==
*[[Chloroacetamide]]
*[[Ethyl chloroacetate]]

==References==
{{Reflist}}

{{organic-compound-stub}}
[[Category:Acetamides]]
[[Category:Nitriles]]

Chloranilic acid

2024-10-21T08:35:29Z

Leiem:

{{Chembox
| Reference=<ref>{{ cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/c8136?lang=en&region=US | title = Chloranilic acid | publisher = [[Sigma-Aldrich]] }}</ref>
| ImageFile = Chloranilic acid.svg
| ImageSize = 150px
| ImageName = Skeletal formula of chloranilic acid
| ImageFile1 = Chloranilic-acid-3D-balls.png
| ImageSize1 = 165px
| ImageName1 = Ball-and-stick model of chloranilic acid
| ImageFile2 = Kyselina chloranilová.jpg
| PIN = 2,5-Dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione
| OtherNames= 2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone 2,5-Dichloro-3,6-dihydroxybenzoquinone
|Section1={{Chembox Identifiers
| InChI = 1/C6H2Cl2O4/c7-1-3(9)5(11)2(8)6(12)4(1)10/h9,12H
| InChIKey = IPPWILKGXFOXHO-UHFFFAOYAU
| CASNo=87-88-7
| ChemSpiderID = 59971
| SMILES=Cl\C1=C(/O)C(=O)C(\Cl)=C(\O)C1=O
| MeSHName=
| PubChem = 66604
| EC_number = 201-780-7
| UNII = YJ8L3BB7Y4
}}
|Section2={{Chembox Properties
| Formula=C6H2Cl2O4
| MolarMass =208.98 g/mol
| Appearance=orange or red crystals or powder
| Density= 1.96 g/cm3<ref name=Andersen>{{cite journal |doi=10.1107/S0365110X67000325|title=The Crystal and Molecular Structure of Hydroxyquinones and Salts of Hydroxyquinones. I. Chloranilic Acid |year=1967 |last1=Andersen |first1=E. K. |journal=Acta Crystallographica |volume=22 |issue=2 |pages=188–191 |doi-access=free }}</ref>
| MeltingPt = ≥300 °C
| BoilingPt =
| pKa = 2.95, 4.97<ref name=cmpx>{{ cite journal | author = Mostafa, S. I. | title = Complexes of 2,5-Dihydroxy-1,4-Benzoquinone and Chloranilic Acid with Second and Third Row Transition Elements | journal = Transition Metal Chemistry | year = 1999 | volume = 24 | issue = 3 | pages = 306–310 | doi = 10.1023/A:1006944124791 | s2cid = 91429728 }}</ref>
}}
|Section3={{Chembox Hazards
| FlashPtC = 135.4
| GHSSignalWord = Warning
| GHSPictograms = {{GHS07}}
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}

'''Chloranilic acid''' is an organic [[Chemical compound|compound]] with the [[chemical formula]] {{Chem2|C6Cl2O2(OH)2}}. It is a red-orange solid. The compound is obtained by hydrolysis of [[chloranil]]:
: {{Chem2|C6Cl4O2 + 2 H2O -> C6Cl2O2(OH)2 + 2 HCl}}
It is centrosymmetric, planar molecule. It also crystallizes as a dihydrate.<ref name=Andersen/>

Chloranilic acid is a noteworthy hydroxyquinone that is somewhat acidic owing to the presence of the two chloride substituents. The conjugate base, C6H2Cl2O42- readily forms [[coordination complexes]] often linking pairs of many metal ions.<ref name=cmpx/>

==See also==
* [[Chloranil]]

==References==
{{reflist}}

{{ketone-stub}}

[[Category:Chloroarenes]]
[[Category:1,4-Benzoquinones]]
[[Category:Hydroxybenzoquinones]]
[[Category:Hydroquinones]]

Malonyl chloride

2024-10-21T08:29:23Z

Leiem: add ref

{{Chembox

| ImageFile = CH2(COCl)2.png
| ImageSize =
| ImageAlt =

| PIN = Propanedioyl dichloride<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=797 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames =

| Section1 = {{Chembox Identifiers
| CASNo = 1663-67-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PDF3ZL8FTK
| PubChem = 74269
| EC_number = 216-772-9
| ChemSpiderID = 66875
| InChI=1S/C3H2Cl2O2/c4-2(6)1-3(5)7/h1H2
| InChIKey = SXYFKXOFMCIXQW-UHFFFAOYSA-N
| SMILES = C(C(=O)Cl)C(=O)Cl
}}
| Section2 = {{Chembox Properties
| C=3 | O=2 | Cl = 2 | H=2
| MolarMass =
| Appearance = colorless liquid
| Density =
| MeltingPt =
| BoilingPtC = 58
| BoilingPt_notes = 28 mm Hg
| Solubility =
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS05}}
| GHSSignalWord= Danger
| HPhrases = {{H-phrases|226|314}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Malonyl chloride''' is the organic compound with the formula CH2(COCl)2. It is the [[acyl chloride]] derivative of [[malonic acid]]. It is a colorless liquid although samples are often deeply colored owing to impurities. The compound degrades at room temperature after a few days. It used as a reagent in [[organic synthesis]].<ref name=Thomas>{{Cite encyclopedia|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|title=Malonyl Chloride|year=2001|doi=10.1002/047084289X.rm016|author=Thomas Ziegler|isbn=0471936235}}</ref>

==Synthesis and reactions==
Malonyl chloride can be synthesized from [[malonic acid]] in [[thionyl chloride]].<ref>{{Cite journal|author= Chittaranjan Raha|title=Di-tert-Butyl Malonate|year=1953|volume=33|page=20|url=http://orgsyn.org/demo.aspx?prep=CV4P0261|journal=Organic Syntheses|doi=10.15227/orgsyn.034.0026}}</ref> As a [[bifunctional compound]], it is used in the preparation of a number of cyclic compounds by di[[acylation]]. Heating in the presence of non-nucleophilic base gives the [[ketene]] derivative O=C=C(H)COCl.<ref name=Thomas />

==References==
{{Reflist}}

{{Navbox acyl chlorides}}

[[Category:Acyl chlorides]]

{{organic-compound-stub}}

Malonyl chloride

2024-10-21T08:24:13Z

Leiem:

{{Chembox

| ImageFile = CH2(COCl)2.png
| ImageSize =
| ImageAlt =

| PIN = Propanedioyl dichloride<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=797 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames =

| Section1 = {{Chembox Identifiers
| CASNo = 1663-67-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PDF3ZL8FTK
| PubChem = 74269
| EC_number = 216-772-9
| ChemSpiderID = 66875
| InChI=1S/C3H2Cl2O2/c4-2(6)1-3(5)7/h1H2
| InChIKey = SXYFKXOFMCIXQW-UHFFFAOYSA-N
| SMILES = C(C(=O)Cl)C(=O)Cl
}}
| Section2 = {{Chembox Properties
| C=3 | O=2 | Cl = 2 | H=2
| MolarMass =
| Appearance = colorless liquid
| Density =
| MeltingPt =
| BoilingPtC = 58
| BoilingPt_notes = 28 mm Hg
| Solubility =
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS05}}
| GHSSignalWord= Danger
| HPhrases = {{H-phrases|226|314}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Malonyl chloride''' is the organic compound with the formula CH2(COCl)2. It is the [[acyl chloride]] derivative of [[malonic acid]]. It is a colorless liquid although samples are often deeply colored owing to impurities. The compound degrades at room temperature after a few days. It used as a reagent in [[organic synthesis]].<ref>{{Cite encyclopedia|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|title=Malonyl Chloride|year=2001|doi=10.1002/047084289X.rm016|author=Thomas Ziegler|isbn=0471936235}}</ref>

==Synthesis and reactions==
Malonyl chloride can be synthesized from [[malonic acid]] in [[thionyl chloride]].<ref>{{Cite journal|author= Chittaranjan Raha|title=Di-tert-Butyl Malonate|year=1953|volume=33|page=20|url=http://orgsyn.org/demo.aspx?prep=CV4P0261|journal=Organic Syntheses|doi=10.15227/orgsyn.034.0026}}</ref> As a [[bifunctional compound]], it is used in the preparation of a number of cyclic compounds by di[[acylation]]. Heating in the presence of non-nucleophilic base gives the [[ketene]] derivative O=C=C(H)COCl.

==References==
{{Reflist}}

{{Navbox acyl chlorides}}

[[Category:Acyl chlorides]]

{{organic-compound-stub}}

3,3-Dimethylbutyraldehyde

2024-10-07T06:59:46Z

Leiem: deg C

{{Short description|Organic compound}}
{{Chembox
| ImageFile = 3,3-dimethylbutyraldehyde structuur.png
| PIN = 3,3-Dimethylbutanal
| OtherNames = {{Unbulleted list|Neohexanal|3,3-Dimethylbutyraldehyde|3-Methylisovaleraldehyde|''tert''-Butylacetaldehyde}}
|Section1={{Chembox Identifiers
| CASNo = 2987-16-8
| PubChem = 76335
| UNII = CAM6HD7JKI
| SMILES = CC(C)(C)CC=O
| StdInChI = InChI=1S/C6H12O/c1-6(2,3)4-5-7/h5H,4H2,1-3H3
| StdInChIKey = LTNUSYNQZJZUSY-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=6 | H=12 | O=1
| Appearance = clear fluid<ref name="Sigma">{{Sigma-Aldrich|Aldrich|id=359904|name=3,3-Dimethylbutyraldehyd|accessdate=2020-12-18}}</ref>
| Odor = unpleasant
| Density = 0.798 g/cm3 (at {{convert|25|C}})
| MeltingPtC = -24
| BoilingPtC = 104 to 106
| Solubility = 7.6 g/L
}}
|Section4={{Chembox Hazards
| Hazards_ref = <ref name="Sigma" />
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| HPhrases = {{H-phrases|225|315|319|335}}
| PPhrases = {{P-phrases|210|302+352|305+351+338}}
}}
}}

'''3,3-Dimethylbutyraldehyde''' is a branched saturated aliphatic [[aldehyde]] with an unpleasant odor that is used in the synthesis of [[perfume|perfumes]] and [[neotame]].<ref name="prakash">{{cite journal |last1=Prakash |first1=Indra |last2=Bishay |first2=Ihab |last3=Schroeder |first3=Steve |title=Neotame: Synthesis, Stereochemistry and Sweetness |journal=Synthetic Communications |date=1 December 1999 |volume=29 |issue=24 |page=4461-4467 |doi=10.1080/00397919908086610 |access-date=12 November 2021 |url=https://www.tandfonline.com/doi/pdf/10.1080/00397919908086610}}</ref>

== Synthesis ==
It can be synthesized from [[3,3-dimethyl-1-butanol]] via a copper catalyzed [[dehydrogenation]].<ref name="m578">{{cite journal | last=Tanielyan | first=Setrak K. | last2=Augustine | first2=Robert L. | title=Synthesis of 3,3-Dimethylbutanol and 3,3-Dimethylbutanal, Important Intermediates in the Synthesis of Neotame | journal=Topics in Catalysis | publisher=Springer Science and Business Media LLC | volume=55 | issue=7-10 | date=2012-06-22 | issn=1022-5528 | doi=10.1007/s11244-012-9841-z | pages=625–630}}</ref>

==References==
{{Reflist}}
== Other sources ==
K. Satyavathi, P.B. Raju, K.V. Bupesh, T.N.R. Kiran (2010), "Mini Review. Neotame: High Intensity Low Caloric Sweetener", ''Asian J. Chem.'' 7 (22).

[[Category:Alkanals]]
[[Category:Foul-smelling chemicals]]

Benzoylphenylurea

2024-09-27T02:15:21Z

Leiem: CAS RN; name

{{Short description|Class of chemical compounds}}
{{Orphan|date=September 2024}}
{{Chembox
| IUPACNAME = ''N''-carbamoyl-''N''-phenylbenzamide
| OtherNames = ''N''-(aminocarbonyl)-''N''-phenylbenzamide
|Section1={{Chembox Identifiers
| CASNo = 1195179-46-4
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEMBL = 4650348
| ChemSpiderID = 14672653
| PubChem = 19851629
| UNII = M10I9SO6RR
| StdInChI=1S/C14H12N2O2/c15-14(18)16(12-9-5-2-6-10-12)13(17)11-7-3-1-4-8-11/h1-10H,(H2,15,18)
| StdInChIKey = XYFMGGWVGACNEC-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)C(=O)N(C2=CC=CC=C2)C(=O)N
}}
|Section2={{Chembox Properties
|C=14|H=12|N=2|O=2
}}
|Section8={{Chembox Related
}}
}}

'''Benzoylphenylurea''' (BPU) is a class of chemical compounds known for its insecticidal properties and applications in cancer treatment.

== Insecticidal use ==
Benzoylphenylurea was first identified in the 1970s as an effective inhibitor of [[chitin]] biosynthesis in insects. These compounds disrupt molting and development, making them useful as insect growth regulators. BPUs such as [[lufenuron]] and [[diflubenzuron]] are commonly used for pest control due to their selectivity and low toxicity to vertebrates.<ref name="chen2007">{{Cite journal |last=Chen |first=Li |title=Insecticidal Benzoylphenylurea-S-Carbamate: A New Propesticide with Two Effects of Both Benzoylphenylureas and Carbamates |journal=Journal of Agricultural and Food Chemistry |volume=55 |issue=7 |pages=2659–2663 |doi=10.1021/jf063564g |year=2007|pmid=17348679 }}</ref>

== Antitumor activity ==
BPUs have also demonstrated antitumor activity. Studies have shown that BPU analogues can inhibit [[tubulin]] polymerization, thereby disrupting cell division in cancer cells. These compounds, especially sulfur analogues, have exhibited significant potency against various cancer cell lines, including pancreatic and prostate cancers.<ref name="hallur2006">{{Cite journal |last=Hallur |first=Gurulingappa |title=Benzoylphenylurea Sulfur Analogues with Potent Antitumor Activity |journal=Journal of Medicinal Chemistry |volume=49 |issue=7 |pages=2357–2360 |doi=10.1021/jm051261s |year=2006|pmid=16570932 }}</ref>

== Mechanism of action ==
In insects, BPUs inhibit chitin synthesis by targeting chitin synthase, preventing proper exoskeleton formation. In cancer treatment, BPU analogues interfere with microtubule formation, disrupting the proliferation of cancer cells.<ref name="gangishetti2009">{{Cite journal |last=Gangishetti |first=Umesh |title=Effects of Benzoylphenylurea on Chitin Synthesis and Orientation in the Cuticle of the Drosophila Larva |journal=European Journal of Cell Biology |volume=88 |issue=2 |pages=167–180 |doi=10.1016/j.ejcb.2008.09.002 |year=2009|pmid=18996617 }}</ref>

== References ==
{{reflist}}

[[Category:Cancer research]]
[[Category:Insecticides]]
[[Category:Benzamides]]
[[Category:Anilides]]
[[Category:Ureas]]

Wikipedia:Reference desk/Science

2024-09-25T15:38:27Z

Leiem: /* Etymology of wheldone */

<noinclude>{{Wikipedia:Reference desk/header|WP:RD/S}}
[[Category:Non-talk pages that are automatically signed]]
[[Category:Pages automatically checked for incorrect links]]
[[Category:Wikipedia resources for researchers]]
[[Category:Wikipedia help forums]]
[[Category:Wikipedia reference desk|Science]]
[[Category:Wikipedia help pages with dated sections]] </noinclude>

= September 10 =

== Recatquista ==

In looking into my answer to [[Wikipedia:Reference_desk/Science#Cat|Cat]] above, I stumbled on the [[quantum immortality]] article, and I feel dumber for having read it. I'm getting that it's premised on some mystic consciousness woo, but I still don't understand what the experimenter dying, or the experimenter understanding QM, has to do with anything. Or does the thought experiment just exclude hard materialists at its premise? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 04:23, 10 September 2024 (UTC)

:The basic argument has nothing to do with consciousness. In the [[many worlds interpretation]], a measurement that causes the wave function to collapse to a definite state actually makes the universe split into two: one for each of the two possible outcomes. Now imagine a [[qubit]] being measured again and again, until the outcome is 0. Each time there will be a branch in the tree of universes in which the outcome was 1, so there is a path in which the qubit never "dies". The death of a living organism is the result of many measurements eventually leading to its demise, but, analogously to the immortal qubit, there should be a path in which all outcomes are such that they keep the organism alive and, ''pace'' Tegmark, well.  --[[User talk:Lambiam#top|Lambiam]] 08:36, 10 September 2024 (UTC)
::In the article it says Tegmark's thought experiment "must be virtually certain to kill the experimenter" and "on a time scale shorter than that on which they can become aware of the outcome of the quantum measurement". I don't understand what this has to do with what you're saying about the MWI. It should be sufficient proof enough of MWI to simply have an experiment running measuring the spin of a random qubit that never ever measures 0 (or I guess to see an event in any known process whose expected duration is orders of magnitude smaller than the lifespan of the universe). Or, if personal experience is insisted, I don't see what dying, or instantaneous dying for that matter, has to do with 'traveling' so-to-speak through the many worlds. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 15:34, 10 September 2024 (UTC)
:::In ''your'' universe the qubit may come up 0 while another version of you, in a sister universe, sees a 1. But that other you cannot communicate this outcome to your you.  --[[User talk:Lambiam#top|Lambiam]] 17:31, 10 September 2024 (UTC)
::::Ok? But if I instaneously kill myself I can?
::::I feel like there's a great deal of unarticulated premises about consciousness here that everyone in the article seems to know instinctually, but I am completely lost by. (Not that I can't sympathize, but that there are a lot of interpretations of spiritual consciousness and the self around the world, so I can't follow the logic of the argument until I know what premises they're using.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:40, 10 September 2024 (UTC)
:::::I think bringing in consciousness is a red herring. Everything would go just the same with [[philosophical zombie]]s – the laws of physics don't care.  --[[User talk:Lambiam#top|Lambiam]] 17:48, 10 September 2024 (UTC)
::::::Ok, so then could you explain Tegmark's reasoning in the article? I understand the laws of physics as far as I've studied them, but I'm trying to understand the argument as written (and maybe even salvage the article). [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:57, 10 September 2024 (UTC)
:::::::There isn't much to it. You have two people (let's make them people to make it easy). One is in the box. One is outside the box. The one in the box knows if he is alive or dead. The one outside the box doesn't know if the one inside the box is alive or dead and, therefore, must continue with the assumption that the person in the box is both alive and dead at the same time. What is being done that requires this? Let's assume that the person outside the box is filing taxes for the person inside the box. Is this the final tax statement for someone who is dead or a normal tax statement for someone who is alive? The person outside the box does not know and has to fill out both, one for someone who is dead and one for someone who is alive. Now, let's assume the person in the box is alive. He knows that the person outside the box is filing both and giggles to himself that he making the extra work. But, what if the person inside the box is dead? The person outside the box is treating him as if he is still alive... which is overhyped as "life after death." It isn't that the person in the box is alive. It is that the person outside tbe box is treating them as they are alive (and dead). The complication isn't in the concept of being alive and dead. The complication is in the quantum formulas that use the two states combined. [[Special:Contributions/75.136.148.8|75.136.148.8]] ([[User talk:75.136.148.8|talk]]) 17:18, 11 September 2024 (UTC)
::::::::Sorry, but I'm not following what this has to do with Tegmark's 3 conditions in the article I linked at the beginning of this topic header (the question to which you immediately replied), or the subject of the quantum immortality/suicide generally? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 01:05, 12 September 2024 (UTC)
::::::::Your reply suggests that the quantum state of the box is a definite one and that the issue is merely the lack of knowledge of outside observers. This is then in fact a [[local hidden-variable theory]]; such theories do not conform to the rules of [[quantum mechanics]].  --[[User talk:Lambiam#top|Lambiam]] 06:33, 12 September 2024 (UTC)
::::::Sorry, no red herring here. The consciousness is here what makes the superposition its own observer. The basic question is here "How do the equation of Schroedingers cat work if observer and observed are the same, especially if the observer could observe only one of the states?" (A dead observer can not observe) [[Special:Contributions/176.0.144.43|176.0.144.43]] ([[User talk:176.0.144.43|talk]]) 16:26, 12 September 2024 (UTC)
:::::::Did you read the [[quantum immortality]] article? That's the subject of the question. This has nothing to do with Shroedinger's cat. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 16:32, 12 September 2024 (UTC)
::::::::The first sentence in the lede links to Schroedingers cat. How does it not do have anything to do with Schroedingers cat under these circumstances? [[Special:Contributions/176.0.152.191|176.0.152.191]] ([[User talk:176.0.152.191|talk]]) 23:00, 15 September 2024 (UTC)

== Voltage and speed of electrons ==

For a resistance <math>R</math>, a voltage <math>U</math> and a current <math>I</math>, with the relation <math>U=RI</math>, the electrical power is <math>P=UI=RI^2</math> . As <math>I</math> is the intensity of the electron current in a section, that is to say the number of electrons that pass through this section per unit of time. Then should we consider that the number of circulating electrons is constant and proportional to <math>R</math>, therefore with the intensity proportional to their speed which is then considered as the voltage, or a mixture between the number of circulating electrons and their speed? In the latter case what is the rule giving the relationship between the number and the speed of the electrons? [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 08:47, 10 September 2024 (UTC)
:The concept that current flow is the same as electron flow is acceptable for learning about circuits, but it is not real. It is similar to using water flow to explain the concept of electricity. Electrons do move, but very slowly in comparison to electrial current flow. There are many websites and videos that explain the actual flow of electromagnetic waves through a circuit. If you ever happen to get into radio or microwave circuitry, understanding the electromagnetic nature of electricity is important. [[Special:Contributions/12.116.29.106|12.116.29.106]] ([[User talk:12.116.29.106|talk]]) 12:29, 10 September 2024 (UTC)
:Your first sentence is entirely correct. Your second too, assuming that the current is carried by electrons, which is normally the case in solid or liquid metals. Then your question. I don't fully understand the question, in particular the part “the number of circulating electrons is constant and proportional to <math>R</math>”. Both the number of free electrons and the resistance are static properties of the circuit, independent of the voltage or current applied, but with both constant, you cannot say that one is proportional to the other. Otherwise, the answer to the question appears mostly yes, although it's worded in an uncommon way. If you increase voltage, the drift speed of the electrons increases, but the number of free electrons is constant (again, in a solid or liquid metal).
:The density of free electrons (electrons per cubic metre) depends on the material used. In semiconductors, there's a strong temperature dependence too. The specific resistance (ohm-metre) also depends on the material and temperature. The current density (ampère per square metre) equals the free electron density (electrons per cubic metre) times the drift velocity (metres per second) times the electron charge (<math>-1.6 \cdot 10^{-19}</math> coulomb per electron). The current density also equals the local electric field (volts per metre) divided by the specific resistance, none of which are constant throughout the circuit. All of that assuming that magnetic and electrostatic induction can be ignored (i.e., DC) and that electrons get up to speed in a negligible distance compared to the length scale of the circuit. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 12:34, 10 September 2024 (UTC)
::One does not apply a voltage or a current, but only a voltage, which will then give a current depending on the circuit's resistance. So I will clarify my question. I consider the resistance in a restricted circuit volume and having a certain section (elsewhere the resistance is zero), all in a solid. If I understand your answer correctly, the number of (free) electrons moving in the resistance is constant and it is the voltage divided by the resistance which gives the drift velocity of the electrons. I know that this current carries an electromagnetic wave, more precisely a flow of energy and at constant speed. So I am looking for the relationship between the current of the electrons whose number is fixed and the flow of electromagnetic energy whose speed is constant, which gives the equation <math>P = RI^2</math>. If the number of electrons is fixed, it seems logical to me that the voltage is proportional to their drift velocity (speed). Maxwell is for the energy on one side, and on the other, Ampere is for the electrons that carry this energy. f the electrons do not move, there is no electromagnetic wave with its transport of energy. [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 20:48, 10 September 2024 (UTC)
:::The electron drift velocity is proportional to the electric field which has the units volts/meter. See [[Drift velocity]] and [[Electron mobility]]. Our article [[Speed of electricity]] further calculates the medium-dependent electromagnetic wave velocities of their interactions. [[User:Modocc|Modocc]] ([[User talk:Modocc|talk]]) 13:01, 11 September 2024 (UTC)
::::Thanks. It confirms that the voltage and the speed of electrons are proportional. However, I am not sure that "drift velocity" is an appropriate term here because it is zero in an alternative current. It seems to me that the average instantaneous speed of the electrons is more appropriate. [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 19:35, 11 September 2024 (UTC)

== Kinds of Herability ==

Is there one scientific-mathematical test to distinguish between different forms of genetical herability? 
I mean, if a certrain phenotypic property is genetic during Mendel's rules or additiv or something? I wonder whether we are able to find out just by looking at the offsprings and the parent generation. [[Special:Contributions/2A02:8071:60A0:92E0:25A6:B013:4618:1FCD|2A02:8071:60A0:92E0:25A6:B013:4618:1FCD]] ([[User talk:2A02:8071:60A0:92E0:25A6:B013:4618:1FCD|talk]]) 10:20, 10 September 2024 (UTC)

:When looking at individual organisms, you see [[phenotype]]s. The forms of [[heredity]] (biological inheritance) apply to [[genotype]]s. The relationship between genotype and phenotype is not straightforward. If the phenotypical statistics of the offspring of a couple form a typical Mendelian pattern, it is an indication that [[Mendelian inheritance]] is at play, but it is not a proof. And conversely, the absence of a typical Mendelian pattern need not mean the underlying genotypical inheritance is not Mendelian.  --[[User talk:Lambiam#top|Lambiam]] 17:45, 10 September 2024 (UTC)

:Presumably you're referring to [[Heritability]]. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 16:28, 11 September 2024 (UTC)
::The reference to Mendel's rules shows that the OP means heredity (aka inheritance), not heritability.  --[[User talk:Lambiam#top|Lambiam]] 17:14, 11 September 2024 (UTC)
:::See below. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 18:54, 11 September 2024 (UTC)
::::What is below? Did you review the article you linked? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 01:10, 12 September 2024 (UTC)
:::::No, the point is that Lambiam stated the OP was asking about heredity, but it appears the OP was asking about heritability. Though it could be a language issue. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 02:06, 12 September 2024 (UTC)
::There are different kinds of heritability. For instance one way via the rules of Mendelian; some properties are heritabil with [[Additive genetic effects|additive effects]] and others with combinated effects.
::The question is whether there is a methode to make clear via which way one given property is heredite. [[Special:Contributions/2A02:8071:60A0:92E0:1465:9402:7F53:FBFB|2A02:8071:60A0:92E0:1465:9402:7F53:FBFB]] ([[User talk:2A02:8071:60A0:92E0:1465:9402:7F53:FBFB|talk]]) 18:24, 11 September 2024 (UTC)
:::Take a look at the diagram labeled "A ’Broken Stick’ Model" in the article [[Additive genetic effects]]. In general, the observed phenotypic variation is the combined effect of additive and non-additive effects. If it is known that the phenotypic variation is controlled by just a single gene, it is relatively easy to determine which variants the gene has and which variants, if any, are dominant or recessive with regard to their phenotypical expression. But control by just a single gene is exceptional; it implies that the phenotypes can be split into a limited number of discrete categories. The converse implication is not necessarily valid.  --[[User talk:Lambiam#top|Lambiam]] 06:19, 12 September 2024 (UTC)

== Does "narcissist personality disorder" contradict itself? ==

I.e. labelling "excessibe grandiosity" using one person's name (fictional or not) achieves grandiosing that person (narcissus) thus communicates a double message? As in while the word "disorder" says "it is severe", the name of one person trivializes grandiosity. Thus it seems not quite medically consistent. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:37, 10 September 2024 (UTC)

:I fail to see how saying someone has [[narcissistic personality disorder]] (assuming that's what you mean) "achieves grandiosing that person". Do you mean to suggest the term is an [[oxymoron]]? No it isn't. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 12:59, 10 September 2024 (UTC)
:You misread what I said. Your comment "grandiosing that person" is not what I said. I said it grandioses "narcissus". I also didn't use the word "oxymoron". I think there is no need to introduxe extra terminology. My question was sufficiently clear. "No it isn't" is an unuseful/not very dilligent reply. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 13:19, 10 September 2024 (UTC)
::I said "grandiosing that person" about the (fictional) person whose name is used (narcissus), not a person diagnosed with NPD. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 13:22, 10 September 2024 (UTC)
:::Thank you for clarifying that you are referring to the mythological [[Narcissus (mythology)|Narcissus]]. The capital letter makes all the difference. I still don't see how the label is grandiose. If anything it demeans him. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 14:22, 10 September 2024 (UTC)
::::Your sneering/snobbery about "capitalization" doesn't contribute to making this reference desk a welcoming place.
::::Grandness as I think to understand it doesn't mean "good" nor "bad", it means great, and a lot of attention is still making a person great, the same way a "great dictator" can be written about as great without being written about as "good". [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:41, 14 September 2024 (UTC)
::"My question was sufficiently clear." No, it wasn't. You have multiple spelling and grammar errors as well as just odd phrasings that make it very diffcult to understand what you are trying to ask.--[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 10:55, 12 September 2024 (UTC)
:::PS- Shantavira's "no, it isn't" was obviously in answer to the question of whether the phrase is an oxymoron.--[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 11:13, 12 September 2024 (UTC)
::::If you could spot my spelling errors than you admit that you knew what the words were that I intended, and thus didn't detract from the readability.
::::I never asked "whether the phrase is an oxymoron", you introduced that question.
::::As I have already said, the amount of effort in "no it isn't" makes your reply completely useless. That reply has NO educational value, it doesn't provide any tools that would enable me to understand an answer to my question, rather you have only encouraged me to blindly copy an answer without understanding anything about the reasons you see for that answer. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:44, 14 September 2024 (UTC)
:::::I for one did not understand the question as you had intended it. I thought that you used ''[[wikt:narcissus|narcissus]]'' as a common noun for a person suffering from [[narcissistic personality disorder]] (although the term is usually used as a synonym of ''[[wikt:Adonis|adonis]]'').  --[[User talk:Lambiam#top|Lambiam]] 18:37, 14 September 2024 (UTC)
:::::You need to explain your concept of "grandiosing" before anyone can give you a satisfactory reply. We don't know what it means so we can't tell where to start. What are some synonyms, how does it trivialize grandiosity (someone's grandiosity? the quality of being grandiose itself?) to attach a name to the word "disorder"? [[User:HansVonStuttgart|HansVonStuttgart]] ([[User talk:HansVonStuttgart|talk]]) 09:52, 16 September 2024 (UTC)
These definitions need to be kept in sight:
[[Narcissus (mythology)|Narcissus]] A fictional character in ancient Greek myth whose self admiration comically exceeded his common sense. We spell Narcissus with a capital first letter for no other reason than that his is a proper name. We derive from Narcissus by analogy (a relationship of resemblence) [[Narcissism|narcissism]] that is a personality style of unusually high preoccupation with oneself and one's own needs. Only when a narcissistic personality is so extreme as to impair mental well-being and [[Psychosocial]] development will it be declared a mental disorder, this called [[Narcissistic personality disorder|narcissistic personality disorder]] (NPD). I see nothing illogical or contradictory in this understanding of NPD. However the OP is here to argue an objection to the term NPD that is difficult to understand and proceeds quite combatively to take issue with every responder to their question.

[[Grandiosity]] is simply an unrealistic sense of unique superiority that is often present in NPD and is in no way a genuine achievement. It is meaningless to talk of grandiosing a third party when grandiosity is only what the NPD feels about themself. The language becomes confused if the real person with NPD is called "narcissus" or "Narcissus" which both seem merely rude. The OP snaps impolitely[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1245003123&oldid=1245000791] at Shantaviraj who actually read the words "achieves grandiosing that person" correctly and attacks Shantaviraj for offering a tentative answer to the unclear question. The OP returning[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1245003434&oldid=1245003123] just 3 minutes later to shore up their own thoughtless contradiction is what I qualify as a snapping behaviour. The OP's next accusation about "Your sneering/snobbery..." is calculated insult. I conclude that despite the best-effort responses from Shantaviraj, Khajidha, Lambiam and HansVonStuttgart this OP is not here to accept any help in the form of references that we could give and that further engagement on the OP's issue is a waste of time. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 12:40, 17 September 2024 (UTC)

:I take "grandiosing" (not an existing word in English, though its formation is transparent) to be an error for '[[wiktionary:aggrandize|aggrandising]]'. {The poster formerly known as 87.81.230.195} [[Special:Contributions/94.6.83.137|94.6.83.137]] ([[User talk:94.6.83.137|talk]]) 14:46, 17 September 2024 (UTC)

== Any observed similarity between [[Hero syndrome]] and [[FDIA]]? ==

I read on the Hero syndrome page.. "The term is used to describe individuals who constantly seek appraisal for valiant or philanthropic acts, especially by creating a harmful situation which they then can resolve". Isn't that very similar to FDIA? There is no mention on the Hero syndrome page of FDIA.

The FDIA page even literally mentions.. "These proxies then gain personal attention and support by taking on this fictitious 'hero role' and receive positive attention from others, by appearing to care for and save their so-called sick child", but doesn't reference the Hero syndrome page either. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:56, 10 September 2024 (UTC)

:A statement such as "A is a kind of B" requires [[WP:V|a reliable source]]. One issue why such sources are hard to come by in this case may be that Factitious Disorder is a recognized disorder (300.19 in [[DSM-5]], F68.1 in [[ICD-10]]), whereas "hero syndrome" is journalese and has no generally accepted diagnostic criteria.  --[[User talk:Lambiam#top|Lambiam]] 17:17, 10 September 2024 (UTC)
::Thank you for the answer. Is there not a lot of literature about hero syndrome? Some of the cases mentioned on the wikipedia page (e.g. a police officer setting a bomb to "be seen defusing it") seem quite high profile, I'd expect to be some literature about that. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:51, 14 September 2024 (UTC)
:::I don't see much that makes the connection, but here is a directly relevant passage in a RS, a book by the title ''The Munchausen Complex: Socialization of Violence and Abuse'':
::::{{tq|In another manifestation of MSBP, a perpetrators will induce a condition in order to heroically “save” the victim thereby showing they are a concerned caretaker. Sometimes health care providers – including nurses of both sexes – do this. Their actions are considered a type of Munchausen Syndrome by Proxy. This phenomenon may very well be a distinct category of Munchausen that should be researched and redefined as Munchausen Malignant Hero Syndrome.}}[https://books.google.com/books?hl=en]
:::The proposal of the last sentence does not appear to have gained traction.  --[[User talk:Lambiam#top|Lambiam]] 18:26, 14 September 2024 (UTC)
:So, I'm going to try to find a good source for this a little later, Ybllaw, but quickly while I am here now: it is worth noting that typically Munchausen by proxy manifests in a desire to derive sympathy and attention from the manufactured ailment, rather than accolades for heroism. That said, I don't think the two pathologies would be by any means mutually exclusive. ''[[User:Snow Rise|SnowRise]][[User talk:Snow Rise| let's rap]]'' 00:33, 22 September 2024 (UTC)

= September 12 =

== Kidney theft ==

Can you tell me something about the kidney theft gangs working out of Southeast Asia? Having a discussion on a forum about them now. [[Special:Contributions/146.200.107.107|146.200.107.107]] ([[User talk:146.200.107.107|talk]]) 23:41, 12 September 2024 (UTC)
:Have you read [[Organ theft]]?-[[User:Gadfium|Gadfium]] ([[User talk:Gadfium|talk]]) 00:53, 13 September 2024 (UTC)
:What kidney theft gangs working out of Southeast Asia are those then? There are so many traffic fatalities in SEAsia that I'm surprised there would be a market for stolen kidneys. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 04:17, 16 September 2024 (UTC)

= September 14 =

== Atomic electron transition time ==

In Wikipedia article [[Atomic electron transition]] it is written that: "''The time scale of a quantum jump has not been measured experimentally''", why ? [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 12:07, 14 September 2024 (UTC)
:Because nobody knows how to do it (or if they do, they cannot yet implement it in an experiment). An [[attosecond]] is a rather short time. The article lists the shortest laser light pulse created as 43 attoseconds, so that is the shortest time scale that is technically accessible at the moment. But if you have an idea, go for it. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 12:35, 14 September 2024 (UTC)
::There may be a more fundamental reason. Such a measurement would necessarily (I think) require two observations, one essentially being that a some time {{mvar|t}}0 the transition has not yet taken place, the other that at a later time {{mvar|t}}1 the transition has now occurred. Such observations require an [[electromagnetic interaction]], which will unavoidably [[Observer effect (physics)#Particle physics|disturb the observed system]], in particular potentially causing the electron to behave differently. If there is some clever way around this fundamental issue, no one has thought of it.  --[[User talk:Lambiam#top|Lambiam]] 13:07, 14 September 2024 (UTC)
:::Apparently, to date, we do not have the tools precise enough for this measurement. On the other hand, the disturbance of the measurement can be anticipated and circumvented, as in this [https://www.webofscience.com/wos/woscc/full-record/WOS:000289196400005 article] measuring the delay of a photoemission by the 2023 Nobel Prize winner L'Huillier: "''The determination of photoemission time delays requires taking into account the measurement process, involving the interaction with a probing infrared field. This contribution can be estimated using a universal formula and is found to account for a substantial fraction of the measured delay.''" In the past this delay was considered zero, today it is measured around 10 atoseconds. So... [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 21:45, 14 September 2024 (UTC)
::::{{u|Malypaet}}, the imminent development of a practical [[Nuclear clock]], which will be able to measure smaller intervals of time than any possible [[Atomic clock]], may soon enable the precision necessary to measure quantum-jump timescales. {The poster formerly known as 87.81.230.195} [[Special:Contributions/94.6.83.137|94.6.83.137]] ([[User talk:94.6.83.137|talk]]) 14:36, 17 September 2024 (UTC)

== How does one deal with equations with incorrect units? ==

Specifically thinking [https://iopscience.iop.org/article/10.3847/1538-4357/ac779c/pdf this one], equation 31. It doesn't seem to yield a metric unit when you put in some values. [[User:Jo-Jo Eumerus|Jo-Jo Eumerus]] ([[User talk:Jo-Jo Eumerus|talk]]) 16:52, 14 September 2024 (UTC)
:Do you expect us to read and understand the entire paper up to that equation? Maybe you could help us a bit by summarising what the terms stand for, what their units are and why you think the entire equations do not yield "metric" units. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 17:06, 14 September 2024 (UTC)
:It should. All the units in the paper are SI. Script-H in the paper should be heat flux (e.g. conductive thru a 2D surface i.e. an ice sheet), which will be in Joules per second per meter^2. Make sure to write down every step carefully, using the values given in the paper, including the table of constants. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:08, 14 September 2024 (UTC)
::The problem is that the first equation after doing that insertion yields (kg^7*m^11)^(1/10) which is obviously wrong. [[User:JoJo Eumerus mobile|JoJo Eumerus mobile]] ([[User talk:Jo-Jo Eumerus|main talk]]) 18:48, 14 September 2024 (UTC)
:::Ok, I got it to work, to give delta H in meters. The one constant that seemed hidden in the paper was ''b'', but it has the same dimensions as ''b''0 (eqn A2). Also they don't give the [[Coriolis coefficient]] explicitly, but that has rad/sec (1/s) units. Apart from that, all the other constants should be in there. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 19:44, 14 September 2024 (UTC)
::::Is it the [[Coriolis coefficient]] rather than the [[rotation frequency]]? [[User:Jo-Jo Eumerus|Jo-Jo Eumerus]] ([[User talk:Jo-Jo Eumerus|talk]]) 09:02, 15 September 2024 (UTC)
:::::Yes, as defined after Eq. (10) of the paper, ''f'' represents the [[Coriolis coefficient]], which is subsequently used in Eq. (31). [[User:Nanosci|Nanosci]] ([[User talk:Nanosci|talk]]) 16:30, 15 September 2024 (UTC)

= September 15 =

== the dual of polydactyly ==

[[Polydactyly]] happens. But do people ever grow a finger with an extra joint? [[User:Tamfang|—Tamfang]] ([[User talk:Tamfang|talk]]) 05:44, 15 September 2024 (UTC)
:Googling ''finger with an extra joint'' the first hit is our very own article [[Triphalangeal thumb]]. The first page of search results only mentions an extra crease on the little finger, with no underlying extra bones. But scroll down on the results, maybe you'll get lucky! [[Special:Contributions/85.76.83.87|85.76.83.87]] ([[User talk:85.76.83.87|talk]]) 14:54, 15 September 2024 (UTC)

== Gull with injured foot ==

Take a look at [https://youtube.com/shorts/NZZ5fHKz4xE?si=F0plWRF9SYIbThAJ this video] from a YouTube channel I follow. Steven the seagull injured her (yeah, Steven turned out to be female, but the name stuck anyway) foot somehow. Accident, fight, attack by a predator - whatever happened, the webbing between her toes got split. Does anyone know if that will grow back eventually? [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 21:44, 15 September 2024 (UTC)

:From {{slink|Regeneration (biology)#Aves (birds)}}: {{tq|Owing to a limited literature on the subject, birds are believed to have very limited regenerative abilities as adults.}} I was able to find [http://www.majesticwaterfowl.org/mmissue30.htm an issue of a waterfowl newsletter] with a picture of a duck's foot webbing, apparently torn and partially regrown. Based on this, I think it's very likely to grow back ''somewhat'', but perhaps less likely to grow back ''completely''. I'm rooting for Steven though! [[User:Jlwoodwa|jlwoodwa]] ([[User talk:Jlwoodwa|talk]]) 01:52, 16 September 2024 (UTC)
::She's been getting her foot doused with antiseptic and eats a REALLY good diet for an urban gull (fresh fish, fresh meat, mealworms daily), so she's in a better position than most. [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 13:37, 16 September 2024 (UTC)
:Presumably it could only heal if the split was mechanically sealed first. If the surfaces keep moving relative to each other or they get dirty I don't see how the split can heal. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 08:23, 16 September 2024 (UTC)
::Reminds me of [[Paul Temple]]'s wife! [[Special:Contributions/2A00:23C5:E161:9200:D500:7967:3BC2:6E0B|2A00:23C5:E161:9200:D500:7967:3BC2:6E0B]] ([[User talk:2A00:23C5:E161:9200:D500:7967:3BC2:6E0B|talk]]) 10:04, 16 September 2024 (UTC)
::I was thinking that it might grow back from the bottom outwards. Not really sure how it works in gulls, compared to us, if we split that thin bit of flesh between thumb and forefinger. [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 13:34, 16 September 2024 (UTC)
:::My experience with wildlife rehabilitation, including occasional avians and waterfowl, but not gulls, suggests to me that it will not substantially regrow. In most animals with thin membranes of this sort, post-developmental regeneration is extremely limited once the semi-vascularized tissues are torn; the cells are of differentiated types which simply are not capable of interacting in the manner necessary to reconstruct the overall structure, instead prioritizing more localized closure of the wound site. In short, Steven will probably see an uneven healing pattern around the periphery of the torn segment with some thick scarification. I wouldn't expect more than 5-10% of the gap to fill. {{pb}} That said, while webbing is obviously a helpful adaptation for gulls, tears of this sort are not uncommon and typically not life threatening (either through initial infection or dehabilitation). Considering that Steven seems to have a much more robust support network than your average gull and lives in sheltered semi-urban, semi-natural conditions, she can probably be expected to have a fair long life by gull standards. Please feel free to update me about the foot if my conjecture proves wrong: I'd be interested in the outcome. ''[[User:Snow Rise|SnowRise]][[User talk:Snow Rise| let's rap]]'' 00:22, 22 September 2024 (UTC)

= September 18 =

== Is there any physical theory, claiming that every elementary particle can turn into some other elementary particle? ==

[[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 13:05, 18 September 2024 (UTC)

:[[Quark]]s are the only known particles whose electric charges are not [[integer]] multiples of the [[elementary charge]]. Therefore, in physical theories that accept both the [[Standard Model]] and the [[law of charge conservation]], a quark cannot turn into another particle but a quark. But the types of quarks all have different masses, so all such quark–quark changes violate the [[law of conservation of mass]].  --[[User talk:Lambiam#top|Lambiam]] 17:57, 18 September 2024 (UTC)
::If you are referring to a single elementary particle, so why didn't you mention the electron, besides the quark?
::If that's because an electron colliding with a positron turns (together with the positron) into a pair of photons, then also a quark colliding with an anti-quark turns (together with the anti-qurk) into a pair of gluons.
::Anyway, in my question I allow a given elementary particle to collide with its anti-matter for becoming another elementary particle.
::More important: My question is theoretical, so it's not only about known particles, but rather about all possible particles, including those which haven't been discovered yet. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 18:21, 18 September 2024 (UTC)
:::If someone claims all swans are white, it suffices to debunk the claim by finding one purple swan. Maybe there also blue, brown or black swans, but it is not necessary to search for further counterexamples. Likewise, if some physical theory claims every elementary particle can turn into some other elementary particle, it suffices to debunk the claim by finding just one elementary particle that cannot turn into some other elementary particle. I just started with the top line of [[:File:Standard Model of Elementary Particles.svg]]. There may be many other counterexamples (like the [[Higgs boson]]), but why bother to keep searching?
:::The as of yet undiscovered bunkon and trashon, whose properties are still unknown except that they are postulated to be different elementary particles, can turn into each other. A difficulty in finding them is that their properties are unknown, so experimental physicists don't know where to look. There may be many more such pairs, which may never be discovered.  --[[User talk:Lambiam#top|Lambiam]] 10:17, 19 September 2024 (UTC)
::::By mistake, I thought you meant the quark was the only particle that couldn't turn into another particle but a quark, but now I see this was not what you meant, so I take my first sentence back.
::::However, I still emphasize that my question allows a given elementary particle to collide with its anti-matter for becoming another elementary particle.
::::Re. your senetnce: "The as of yet undiscovered...different elementary particles, can turn into each other": Is there any physical theory claiming what you've claimed in that sentence? Actually, this was my original question... [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:44, 19 September 2024 (UTC)
:::::I'm pretty sure that that sentence was a joke. Look at the names: BUNKon and TRASHon. --[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 11:25, 19 September 2024 (UTC)
::::::No "maybe" about black swans. They were recorded by Europeans in [[Swan River Colony|1697]], possibly earlier. [[Special:Contributions/2A00:23D0:F6F:1001:2D07:A712:8909:7D91|2A00:23D0:F6F:1001:2D07:A712:8909:7D91]] ([[User talk:2A00:23D0:F6F:1001:2D07:A712:8909:7D91|talk]]) 11:56, 19 September 2024 (UTC)
::::::All right. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:35, 19 September 2024 (UTC)
::::::: See also [[black swan]] and [[black swan theory]]. -- [[User:JackofOz|Jack of Oz]] [[User talk:JackofOz#top|[pleasantries]]] 18:37, 19 September 2024 (UTC)

::OP may have in mind something more like the particles created from particle-antiparticle annihilation, such as those in the chart at {{slink|Annihilation#Electron%E2%80%93positron_annihilation}}, as opposed to something like the weak decay of quarks.
::It seems to me that OP could mean either: 1) a single elementary particle can spontaneously become another single elementary particle (with the help of another particle that remains unchanged), in which case I think the answer may be no for any particle; or 2) for two given particles, there's an interaction in some condition where it's meaningful to say that one specified particle is in the input, and it becomes in the output the other specified particle [Edit: which may include any number of other particles in the reaction doing anything else]. Not sure (I didn't do particle), but I think (2) might be considered more or less accurate (to the extent the fuzziness of the wording necessarily allows). [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 16:10, 19 September 2024 (UTC)
:::I adopt your option 1# if it means [[Particle decay]], and I adopt your option 2# if it means [[annihilation]] (i.e. by colliding with the anti-particle).
::::
:::But contrary to the way you divided you answer: option 1# for '''all''' particles, or option 2# for '''all''' particles, I didn't exclude a third option which is: option 1# for '''some''' particles, and option 2# for the '''rest''' of the particles (without excluding particles that satisfy both 1# and 2#).
::::
:::All agree, that some particles satisfy option 1#, and that some particles satisfy option 2#.
::::
:::My question is about whether there is any physical theory claiming, that every particle (including any particle that hasn't been discovered yet), satisfies either 1# or 2# (or both). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:25, 20 September 2024 (UTC)
::::I was trying to interpret your question literally. #1 is one single particle becoming one different single particle with everything else unchanged -- this does not happen at all afaik, nor in general in theory ([[User:Lambian]] gives a simple example for quarks in their answer above). #2, the way I worded it, afaik can (and does) happen for all particles in the Standard Model.
::::What I'm trying to convey with this #1/#2 description is that it's not a particularly meaningful one, if you can claim "every elementary can turn into some other elementary particle" just by comparing one reactant to one product in a complex interaction.
::::(As maybe a sorta-ok example, consider the chemical reaction of a strong acid + base into salt + water: HCl + NaOH -> NaCl + H2O. Would you say the HCl (reactant) turns into salt? turns into water? Or does it change nothing at all because both the reactants and products are largely remain just free ions in aqueous solution? This is why I'm not sure what you're trying to ask is very meaningful.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:24, 20 September 2024 (UTC)
:::::I'm '''not''' asking about a single particle becoming one different single particle with everything else unchanged. Let's put it this way: Is there any physical theory claiming that all particles in the [[dark matter]] can turn into other particles? (whether by a decay or by annihilation or by any other way). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 01:30, 22 September 2024 (UTC)
::::::There can never be such a theory. Why? Dark matter is named so because it never interacts with ordinary matter, except by gravity. As soon as it interacts in any other way it's not dark matter anymore but a new kind of ordinary matter. By interaction by gravity no distinction of particles is possible, only sum and distribution of mass is measurable. So dark matter can decay all it want, no human physicists are able to prove it or disprove it. By definition of the word. It may be that some particles, that we now subsume in dark matter, are later discovered to be not dark. And then we would know the conditions where they participate in the normal decay of ordinary matter. But that can never tell us about the real dark matter, as long as there's real dark matter. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 18:20, 23 September 2024 (UTC)
:::Most particles [[Particle decay|decay]] into other particles. The only "stable" ones are [[Electron]]s, [[Proton]]s, [[Photon]]s and (to a degree [[Neutrino oscillation|(see here)]]) [[Neutrino]]s. But even these can (under the right conditions) either [[Electron capture|combine]] or [[Photoelectric effect|"destroy"]] and [[Spontaneous emission|"create"]] with each other. [[Special:Contributions/176.0.165.39|176.0.165.39]] ([[User talk:176.0.165.39|talk]]) 12:20, 20 September 2024 (UTC)
::::These [[Fundamental interaction|interaction]]s can all be depicted in a [[Feynman diagram]] as lines meeting in a vertex. The lines correspond to particles. In a Feynman diagram, a vertex is always the meeting point of three lines. A particle → particle change would correspond to a Feynman diagram in which just two lines meet in a vertex.  --[[User talk:Lambiam#top|Lambiam]] 22:47, 20 September 2024 (UTC)
:::::Or two lines merging in two vertices that are connected by two lines in the form looking like an eye. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 14:24, 23 September 2024 (UTC)
::::Yes, I know that. but you're talking about partciles of the Standard Model, while I'm asking about a theory that claims that '''all''' particles, including those which '''haven't been discovered yet''', can <s>decay</s> turn into other particles. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 01:30, 22 September 2024 (UTC)
:::::In your question and first response you talked about a particle that "can turn into some other elementary particle", and people are trying to clarify what that can mean. But now you're asking about decay: "[[Particle decay]]" is where ''only one'' particle goes in, and some other number of different particles come out, but as others have said there are stable particles that do not decay. (There are of course experimental bounds to what we currently know of this, and there are interesting subtleties in the [https://arxiv.org/pdf/1304.2821 theory for example why a photon does not decay].)
:::::There's no theory which can claim anything meaningful about all particles that have not been discovered yet. A theory predicts new particles, and the theory becoming successful may lead to building experiments to verify empirically the particles ("discover" them, although a "discovery" was equally done when the theory was written).
:::::You could imagine another type of theory that might say all particle physics theories are really at a fundamental level part of X-theory, and in X-theory everything decays into X-dust in 20 billion years, but that's not a particle theory. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 05:48, 22 September 2024 (UTC)
::::::Re. your first paragraph: I'm sorry for not being clear in my recent response. Thanks to your comment, I will make it clearer, as I've alraedy made it in my first post.
::::::Re. your second paragraph: I mean, something like the [[supersymmetric theory]], claiming something about all particles, including those which haven't been discovered yet. So, again, I'm asking whether there's a theory that claims that all particles, including those which haven't been discovered yet, can <s>decay</s> '''turn''' into other particles, whether by a '''[[particle decay|decay]]''' or by '''annihilation''' or by any other way. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:45, 22 September 2024 (UTC)
Although the above discussion may imply that the words "hypothesis" and "theory" can be used interchangeably, a scientific hypothesis is not the same as a scientific theory.

An answer is '''No''', there is no scientific theory that just claims anything. A [[Scientific theory|scientific theory]] offers a generalized explanation of how [[Nature (philosophy)|nature]] works described in such a way that scientific tests should be able to provide [[Empirical evidence|empirical]] support for it, or [[Empirical evidence|empirical]] contradiction ("[[Falsifiability|falsify]]") of it.

The OP's question using the word "theory" to mean a claim that at best will remain unproven or speculative actually looks for a [[Hypothesis]] meaning an educated guess or thought about something that cannot satisfactorily be explained with the present scientific theories. The OP seems to be thinking aloud[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1246958875&oldid=1246954714] a new hypothesis. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 10:37, 22 September 2024 (UTC)
:See [[Supersymmetric theory]]. It claims something about all particles, including those which haven't been discovered yet, and it's still called a "theory". Anyway, I'm not focusing on terminology but rather on an idea: Is there any theory, or a well known hypothesis, or a well known conjecture, or whatever, claiming that all particles, including those which haven't been discovered yet, can turn into other particles, whether by a '''[[particle decay|decay]]''' or by '''annihilation''' or by any other way. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:45, 22 September 2024 (UTC)
::Wikipedia editors are careful about terminology. By "Supersymmetric theory" you link to the article titled [[Supersymmetry]]. Its first line clarifies that it refers not to a theory but a theoretical framework. Read further to see how it anticipates what might characterise a supersymmetry theory without specifying any one for attention. Merely calling a supposed bosonic superpartner to the electron a selectron hardly amounts to a falsifiable hypothesis and obviously says nothing about undiscovered particles. Beside our care with terminology, we are not in the business of prediction. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 09:17, 23 September 2024 (UTC)
:::I've linked to our article [[Supersymmetric theory]], which does exist in Wikipedia, so when I used the term "supersymmetic theory" I used a term used in Wikipedia as well. Indeed, it passes to the article [[Supersymmetry]], but also this article does point out - in its second paragraph - that {{tq|"Dozens of supersymmetric theories exist"}}, whereas the first paragraph of this article - does point out that the suppersymmetry {{tq|"proposes that for every known particle, there exists a partner particle with different spin properties. There have been multiple experiments on supersymmetry that have failed to provide evidence that it exists in nature."}}
:::Anyway, my original question was not about the terminology used in Wikipedeia, but rather about the very idea, and I allow you to call it: theory, theoretical framework, hypothesis, conjecture, proposal, suggestion, idea, or whatever, but the main idea still remains, as long as I understand you and you understand me (I guess this is the case). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:07, 23 September 2024 (UTC)
::Now you only have to define what you mean by particle. For instance in [[Standard Model]] you have the everyday particles ([[Electron]],[[Proton]]...). Nothing of that is stable in your definition. Then you have [[Quark]]. No quarks are ever single. So it is a question of the neighbouring quarks which reactions are possible. But even then there is no stability in your definition. But never is one particle turned into exactly one other particle. Even if that were possible you only have to look at a different level of abstraction and a group of particles would turn into a different group of particles. [[Special:Contributions/176.0.158.114|176.0.158.114]] ([[User talk:176.0.158.114|talk]]) 09:34, 23 September 2024 (UTC)
:::By elementary partice I mean what physicists mean by that term: quarks, leptons, gauge bosons, and also elementray particles that haven't been discovered yet, like axions. Anyway, I really meant what you suggested in yout last sentence: "a group of [elementray] particles would turn into a different group of [elementray] particles". [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:07, 23 September 2024 (UTC)
::::Then I can give you a definite answer. Any group of ordinary matter particles (whether known or not) can turn into another group of particles if they encounter the right conditions (even if the conditions could not be achieved in a laboratory or somewhere near Earth). For dark matter particles that can not scientifically be said. And never will be possible to say with science. If someone says something about changing about dark matter it is and never will be science. That is part of the definition of the word "dark" in "dark matter". If that definition changes nothing about the future I have written will continue to be valid. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 19:28, 23 September 2024 (UTC)
:::::Memorandum: My question was about '''all''' elementary particles, and by elementary partice I mean what physicists mean by that term: quarks, leptons, gauge bosons, and also elementray particles that haven't been discovered yet, like axions.
:::::To sum up: The question is whether, for every group of elementary particles, including those which haven't been discovered yet, '''there exist (what you call) "right conditions"''', under which this group can turn into another group of elementary particles. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 13:10, 24 September 2024 (UTC)
::::::Then as I said all the way before, with my "#2", then if it can be called a "particle", yes you can always make it turn into stuff.
::::::But you should understand what people here are trying to say: this becomes rather meaningless as your understanding of what a theory means, in the sense of the "discovery" of particles, is not very accurate, so when you're trying to force these incompatible notions into your question it makes it difficult to give meaningful answers. (Mine, as I said before, is not particularly meaningful.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 13:28, 24 September 2024 (UTC)
:::::::Theories don't necessarily discuss discoveries, and a theory about elementary paricles doesn't necessarily discuss what you call "discovery" of elementary paricles, it can also say something about elementary paricles that haven't been discovered yet, e.g. gravitons, axions, electrinos, gravitinos, axinos, and the like. Anyway, my question is about all elementary particles, including those which haven't been discovered yet. Are you referring to all of them in your first sentence? [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 18:26, 24 September 2024 (UTC)

= September 21 =

== Variables in chemistry?! ==

I've seen the symbols '''M''' and '''X''' in chemistry, what do they mean? [[User talk:Hydrogen astatide|H]][[User:Hydrogen astatide|At]] 04:07, 21 September 2024 (UTC)
:Well M could represent a metal, and X could represent a [[halogen]] in a chemical formula, eg NaX could be a halide salt of sodium. X is probably F, Cl, Br or I. Theoretically it could be At, but not in any visible amount. If the symbols are in italic text they may represent a number. [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 06:04, 21 September 2024 (UTC)

= September 22 =

== [[B-boson]] ==

Besides a link to our article [[electroweak interaction]] that mentions the [[B-boson]] without telling anything about it, we have no article about this boson. Why?

I'm eager to know some basic data about it, e.g. mass, electric charge, spin, isospin, stability, experiments trying to detect it, and likewise. But... nothing? [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 16:27, 22 September 2024 (UTC)
:<s>You'll find it at [[B meson]].</s> Sorry, although the B meson is a boson, it is not the beast that's mentioned in [[electroweak interaction]]. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 17:23, 22 September 2024 (UTC)
::What a pity. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 08:57, 23 September 2024 (UTC)
::The B-boson isn’t a well-known particle in the standard model of particle physics. Are you thinking of the [[Higgs boson]] that was discovered in 2012? [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 08:47, 23 September 2024 (UTC)
:::No, I'm looking for basic data (e.g. mass charge spin isospin parity etc.) of the B-boson mentioned in our article [[electroweak interaction]]. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 08:57, 23 September 2024 (UTC)
::::The thing is that the B boson doesn't exist as an entity in our Universe. It "exists" before symmetry breaking, but since our world has a broken symmetry the observable bosons are the Z0 and the photon instead of the W3 and B. As the B cannot be observed, many of your questions are moot. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 09:07, 23 September 2024 (UTC)
:::::Got it. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 09:31, 23 September 2024 (UTC)

= September 24 =

== Cloning the Carolina parakeet ==

In theory, would it be possible to clone the extinct [[Carolina parakeet]] by taking whatever existing DNA we have of the species and filling any gaps with DNA from the [[sun conure]] (closest living relative and very common pet) and then putting that into a sun conure egg? I have read that it's very difficult to clone birds though. [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 23:12, 24 September 2024 (UTC)
:Here's an Audubon Magazine [https://www.audubon.org/news/what-would-happen-if-we-brought-birds-back-dead write up] on the topic. It foolishly says that the Carolina parakeet, [[ivory-billed woodpecker]], and [[passenger pigeon]] could be invasive, which is nonsense; only the Carolina parakeet could conceivably be successful beyond its former range. See [[monk parakeet]] for why. [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 23:55, 24 September 2024 (UTC)
::Yes, there's been a lot of talk about removing monk parakeets from areas where they are non-native. But the public tend to get extremely angry about the idea of culling parrots specifically, even to the point of taking direct action when nests are removed. I believe there was even a politician a few years ago who said something along the lines of "absolutely not" when it came to the idea of removing that species being raised by his advisors. [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 00:19, 25 September 2024 (UTC)

:Would you then get an actual Carolina parakeet, or merely a hybrid that kind of looks like it? ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 01:30, 25 September 2024 (UTC)
::Yes, I was thinking that myself. How much of the Carolina parakeet's DNA can be replaced by another (very closely related) species before it can no longer be considered a Carolina parakeet? [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 01:42, 25 September 2024 (UTC)
:::Has the genome of any of these extinct species been mapped? I don't think the article says. But that would be a way to maybe get closer to a real clone. And I understand what they mean by invasive. If a species wasn't someplace, and then appears in that place, by definition it's invasive. That doesn't necessarily mean it will be harmful to other species in that place, but it could be. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 07:18, 25 September 2024 (UTC)

= September 25 =
== Etymology of wheldone ==
What is the etymology of wheldone? The references {{doi|10.1021/acs.orglett.0c00219}} and {{doi|10.1021/acs.jnatprod.4c00649}} only described the chemical as a fungal metabolite isolated from the coculture of Aspergillus fischeri and Xylaria flabelliformis. --[[User:Leiem|Leiem]] ([[User talk:Leiem|talk]]) 09:00, 25 September 2024 (UTC)
:The clue is in the acknowledgments section of the first paper: "This Letter is dedicated to the late Daniel (Dan) Clive Wheldon". And since Wikipedia has everything: [[Dan Wheldon]]. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 09:57, 25 September 2024 (UTC)
::I understand. Thank you! --[[User:Leiem|Leiem]] ([[User talk:Leiem|talk]]) 15:38, 25 September 2024 (UTC)

== Botanical nuts ==

I'm trying to split [[Nut (fruit)]] back into separate articles for food and fruit (because currently a lot of the article content is about things that aren't botanical nuts), but [[User:AlmostReadytoFly/Sandbox/Nut_(fruit)|there's not much left after you strip out the food content]]. Are there any botanists in the house who can recommend sources on botanical nuts and/or weigh in on what should be covered and isn't? [[User:AlmostReadytoFly|AlmostReadytoFly]] ([[User talk:AlmostReadytoFly|talk]]) 10:10, 25 September 2024 (UTC)
:Not a botanist, but I think there's a bit of a problem for having a botanical nut. It is an even fuzzier idea than that of tree. But there's an article on trees so I suppose the could be one like that on nuts. You'd have to decide whether it is a very resticted topic on the botanical idea of a nut which doesn't contain most of what people mean by a nut or a wider one like the article on trees. Would you include pine nuts, coconuts peanuts, and the stones of drupes like almonds or pecans or plums? [[User:NadVolum|NadVolum]] ([[User talk:NadVolum|talk]]) 14:33, 25 September 2024 (UTC)

Wikipedia:Reference desk/Science

2024-09-25T09:00:48Z

Leiem: /* September 25 */

<noinclude>{{Wikipedia:Reference desk/header|WP:RD/S}}
[[Category:Non-talk pages that are automatically signed]]
[[Category:Pages automatically checked for incorrect links]]
[[Category:Wikipedia resources for researchers]]
[[Category:Wikipedia help forums]]
[[Category:Wikipedia reference desk|Science]]
[[Category:Wikipedia help pages with dated sections]] </noinclude>

= September 10 =

== Recatquista ==

In looking into my answer to [[Wikipedia:Reference_desk/Science#Cat|Cat]] above, I stumbled on the [[quantum immortality]] article, and I feel dumber for having read it. I'm getting that it's premised on some mystic consciousness woo, but I still don't understand what the experimenter dying, or the experimenter understanding QM, has to do with anything. Or does the thought experiment just exclude hard materialists at its premise? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 04:23, 10 September 2024 (UTC)

:The basic argument has nothing to do with consciousness. In the [[many worlds interpretation]], a measurement that causes the wave function to collapse to a definite state actually makes the universe split into two: one for each of the two possible outcomes. Now imagine a [[qubit]] being measured again and again, until the outcome is 0. Each time there will be a branch in the tree of universes in which the outcome was 1, so there is a path in which the qubit never "dies". The death of a living organism is the result of many measurements eventually leading to its demise, but, analogously to the immortal qubit, there should be a path in which all outcomes are such that they keep the organism alive and, ''pace'' Tegmark, well.  --[[User talk:Lambiam#top|Lambiam]] 08:36, 10 September 2024 (UTC)
::In the article it says Tegmark's thought experiment "must be virtually certain to kill the experimenter" and "on a time scale shorter than that on which they can become aware of the outcome of the quantum measurement". I don't understand what this has to do with what you're saying about the MWI. It should be sufficient proof enough of MWI to simply have an experiment running measuring the spin of a random qubit that never ever measures 0 (or I guess to see an event in any known process whose expected duration is orders of magnitude smaller than the lifespan of the universe). Or, if personal experience is insisted, I don't see what dying, or instantaneous dying for that matter, has to do with 'traveling' so-to-speak through the many worlds. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 15:34, 10 September 2024 (UTC)
:::In ''your'' universe the qubit may come up 0 while another version of you, in a sister universe, sees a 1. But that other you cannot communicate this outcome to your you.  --[[User talk:Lambiam#top|Lambiam]] 17:31, 10 September 2024 (UTC)
::::Ok? But if I instaneously kill myself I can?
::::I feel like there's a great deal of unarticulated premises about consciousness here that everyone in the article seems to know instinctually, but I am completely lost by. (Not that I can't sympathize, but that there are a lot of interpretations of spiritual consciousness and the self around the world, so I can't follow the logic of the argument until I know what premises they're using.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:40, 10 September 2024 (UTC)
:::::I think bringing in consciousness is a red herring. Everything would go just the same with [[philosophical zombie]]s – the laws of physics don't care.  --[[User talk:Lambiam#top|Lambiam]] 17:48, 10 September 2024 (UTC)
::::::Ok, so then could you explain Tegmark's reasoning in the article? I understand the laws of physics as far as I've studied them, but I'm trying to understand the argument as written (and maybe even salvage the article). [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:57, 10 September 2024 (UTC)
:::::::There isn't much to it. You have two people (let's make them people to make it easy). One is in the box. One is outside the box. The one in the box knows if he is alive or dead. The one outside the box doesn't know if the one inside the box is alive or dead and, therefore, must continue with the assumption that the person in the box is both alive and dead at the same time. What is being done that requires this? Let's assume that the person outside the box is filing taxes for the person inside the box. Is this the final tax statement for someone who is dead or a normal tax statement for someone who is alive? The person outside the box does not know and has to fill out both, one for someone who is dead and one for someone who is alive. Now, let's assume the person in the box is alive. He knows that the person outside the box is filing both and giggles to himself that he making the extra work. But, what if the person inside the box is dead? The person outside the box is treating him as if he is still alive... which is overhyped as "life after death." It isn't that the person in the box is alive. It is that the person outside tbe box is treating them as they are alive (and dead). The complication isn't in the concept of being alive and dead. The complication is in the quantum formulas that use the two states combined. [[Special:Contributions/75.136.148.8|75.136.148.8]] ([[User talk:75.136.148.8|talk]]) 17:18, 11 September 2024 (UTC)
::::::::Sorry, but I'm not following what this has to do with Tegmark's 3 conditions in the article I linked at the beginning of this topic header (the question to which you immediately replied), or the subject of the quantum immortality/suicide generally? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 01:05, 12 September 2024 (UTC)
::::::::Your reply suggests that the quantum state of the box is a definite one and that the issue is merely the lack of knowledge of outside observers. This is then in fact a [[local hidden-variable theory]]; such theories do not conform to the rules of [[quantum mechanics]].  --[[User talk:Lambiam#top|Lambiam]] 06:33, 12 September 2024 (UTC)
::::::Sorry, no red herring here. The consciousness is here what makes the superposition its own observer. The basic question is here "How do the equation of Schroedingers cat work if observer and observed are the same, especially if the observer could observe only one of the states?" (A dead observer can not observe) [[Special:Contributions/176.0.144.43|176.0.144.43]] ([[User talk:176.0.144.43|talk]]) 16:26, 12 September 2024 (UTC)
:::::::Did you read the [[quantum immortality]] article? That's the subject of the question. This has nothing to do with Shroedinger's cat. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 16:32, 12 September 2024 (UTC)
::::::::The first sentence in the lede links to Schroedingers cat. How does it not do have anything to do with Schroedingers cat under these circumstances? [[Special:Contributions/176.0.152.191|176.0.152.191]] ([[User talk:176.0.152.191|talk]]) 23:00, 15 September 2024 (UTC)

== Voltage and speed of electrons ==

For a resistance <math>R</math>, a voltage <math>U</math> and a current <math>I</math>, with the relation <math>U=RI</math>, the electrical power is <math>P=UI=RI^2</math> . As <math>I</math> is the intensity of the electron current in a section, that is to say the number of electrons that pass through this section per unit of time. Then should we consider that the number of circulating electrons is constant and proportional to <math>R</math>, therefore with the intensity proportional to their speed which is then considered as the voltage, or a mixture between the number of circulating electrons and their speed? In the latter case what is the rule giving the relationship between the number and the speed of the electrons? [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 08:47, 10 September 2024 (UTC)
:The concept that current flow is the same as electron flow is acceptable for learning about circuits, but it is not real. It is similar to using water flow to explain the concept of electricity. Electrons do move, but very slowly in comparison to electrial current flow. There are many websites and videos that explain the actual flow of electromagnetic waves through a circuit. If you ever happen to get into radio or microwave circuitry, understanding the electromagnetic nature of electricity is important. [[Special:Contributions/12.116.29.106|12.116.29.106]] ([[User talk:12.116.29.106|talk]]) 12:29, 10 September 2024 (UTC)
:Your first sentence is entirely correct. Your second too, assuming that the current is carried by electrons, which is normally the case in solid or liquid metals. Then your question. I don't fully understand the question, in particular the part “the number of circulating electrons is constant and proportional to <math>R</math>”. Both the number of free electrons and the resistance are static properties of the circuit, independent of the voltage or current applied, but with both constant, you cannot say that one is proportional to the other. Otherwise, the answer to the question appears mostly yes, although it's worded in an uncommon way. If you increase voltage, the drift speed of the electrons increases, but the number of free electrons is constant (again, in a solid or liquid metal).
:The density of free electrons (electrons per cubic metre) depends on the material used. In semiconductors, there's a strong temperature dependence too. The specific resistance (ohm-metre) also depends on the material and temperature. The current density (ampère per square metre) equals the free electron density (electrons per cubic metre) times the drift velocity (metres per second) times the electron charge (<math>-1.6 \cdot 10^{-19}</math> coulomb per electron). The current density also equals the local electric field (volts per metre) divided by the specific resistance, none of which are constant throughout the circuit. All of that assuming that magnetic and electrostatic induction can be ignored (i.e., DC) and that electrons get up to speed in a negligible distance compared to the length scale of the circuit. [[User:PiusImpavidus|PiusImpavidus]] ([[User talk:PiusImpavidus|talk]]) 12:34, 10 September 2024 (UTC)
::One does not apply a voltage or a current, but only a voltage, which will then give a current depending on the circuit's resistance. So I will clarify my question. I consider the resistance in a restricted circuit volume and having a certain section (elsewhere the resistance is zero), all in a solid. If I understand your answer correctly, the number of (free) electrons moving in the resistance is constant and it is the voltage divided by the resistance which gives the drift velocity of the electrons. I know that this current carries an electromagnetic wave, more precisely a flow of energy and at constant speed. So I am looking for the relationship between the current of the electrons whose number is fixed and the flow of electromagnetic energy whose speed is constant, which gives the equation <math>P = RI^2</math>. If the number of electrons is fixed, it seems logical to me that the voltage is proportional to their drift velocity (speed). Maxwell is for the energy on one side, and on the other, Ampere is for the electrons that carry this energy. f the electrons do not move, there is no electromagnetic wave with its transport of energy. [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 20:48, 10 September 2024 (UTC)
:::The electron drift velocity is proportional to the electric field which has the units volts/meter. See [[Drift velocity]] and [[Electron mobility]]. Our article [[Speed of electricity]] further calculates the medium-dependent electromagnetic wave velocities of their interactions. [[User:Modocc|Modocc]] ([[User talk:Modocc|talk]]) 13:01, 11 September 2024 (UTC)
::::Thanks. It confirms that the voltage and the speed of electrons are proportional. However, I am not sure that "drift velocity" is an appropriate term here because it is zero in an alternative current. It seems to me that the average instantaneous speed of the electrons is more appropriate. [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 19:35, 11 September 2024 (UTC)

== Kinds of Herability ==

Is there one scientific-mathematical test to distinguish between different forms of genetical herability? 
I mean, if a certrain phenotypic property is genetic during Mendel's rules or additiv or something? I wonder whether we are able to find out just by looking at the offsprings and the parent generation. [[Special:Contributions/2A02:8071:60A0:92E0:25A6:B013:4618:1FCD|2A02:8071:60A0:92E0:25A6:B013:4618:1FCD]] ([[User talk:2A02:8071:60A0:92E0:25A6:B013:4618:1FCD|talk]]) 10:20, 10 September 2024 (UTC)

:When looking at individual organisms, you see [[phenotype]]s. The forms of [[heredity]] (biological inheritance) apply to [[genotype]]s. The relationship between genotype and phenotype is not straightforward. If the phenotypical statistics of the offspring of a couple form a typical Mendelian pattern, it is an indication that [[Mendelian inheritance]] is at play, but it is not a proof. And conversely, the absence of a typical Mendelian pattern need not mean the underlying genotypical inheritance is not Mendelian.  --[[User talk:Lambiam#top|Lambiam]] 17:45, 10 September 2024 (UTC)

:Presumably you're referring to [[Heritability]]. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 16:28, 11 September 2024 (UTC)
::The reference to Mendel's rules shows that the OP means heredity (aka inheritance), not heritability.  --[[User talk:Lambiam#top|Lambiam]] 17:14, 11 September 2024 (UTC)
:::See below. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 18:54, 11 September 2024 (UTC)
::::What is below? Did you review the article you linked? [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 01:10, 12 September 2024 (UTC)
:::::No, the point is that Lambiam stated the OP was asking about heredity, but it appears the OP was asking about heritability. Though it could be a language issue. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 02:06, 12 September 2024 (UTC)
::There are different kinds of heritability. For instance one way via the rules of Mendelian; some properties are heritabil with [[Additive genetic effects|additive effects]] and others with combinated effects.
::The question is whether there is a methode to make clear via which way one given property is heredite. [[Special:Contributions/2A02:8071:60A0:92E0:1465:9402:7F53:FBFB|2A02:8071:60A0:92E0:1465:9402:7F53:FBFB]] ([[User talk:2A02:8071:60A0:92E0:1465:9402:7F53:FBFB|talk]]) 18:24, 11 September 2024 (UTC)
:::Take a look at the diagram labeled "A ’Broken Stick’ Model" in the article [[Additive genetic effects]]. In general, the observed phenotypic variation is the combined effect of additive and non-additive effects. If it is known that the phenotypic variation is controlled by just a single gene, it is relatively easy to determine which variants the gene has and which variants, if any, are dominant or recessive with regard to their phenotypical expression. But control by just a single gene is exceptional; it implies that the phenotypes can be split into a limited number of discrete categories. The converse implication is not necessarily valid.  --[[User talk:Lambiam#top|Lambiam]] 06:19, 12 September 2024 (UTC)

== Does "narcissist personality disorder" contradict itself? ==

I.e. labelling "excessibe grandiosity" using one person's name (fictional or not) achieves grandiosing that person (narcissus) thus communicates a double message? As in while the word "disorder" says "it is severe", the name of one person trivializes grandiosity. Thus it seems not quite medically consistent. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:37, 10 September 2024 (UTC)

:I fail to see how saying someone has [[narcissistic personality disorder]] (assuming that's what you mean) "achieves grandiosing that person". Do you mean to suggest the term is an [[oxymoron]]? No it isn't. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 12:59, 10 September 2024 (UTC)
:You misread what I said. Your comment "grandiosing that person" is not what I said. I said it grandioses "narcissus". I also didn't use the word "oxymoron". I think there is no need to introduxe extra terminology. My question was sufficiently clear. "No it isn't" is an unuseful/not very dilligent reply. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 13:19, 10 September 2024 (UTC)
::I said "grandiosing that person" about the (fictional) person whose name is used (narcissus), not a person diagnosed with NPD. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 13:22, 10 September 2024 (UTC)
:::Thank you for clarifying that you are referring to the mythological [[Narcissus (mythology)|Narcissus]]. The capital letter makes all the difference. I still don't see how the label is grandiose. If anything it demeans him. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 14:22, 10 September 2024 (UTC)
::::Your sneering/snobbery about "capitalization" doesn't contribute to making this reference desk a welcoming place.
::::Grandness as I think to understand it doesn't mean "good" nor "bad", it means great, and a lot of attention is still making a person great, the same way a "great dictator" can be written about as great without being written about as "good". [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:41, 14 September 2024 (UTC)
::"My question was sufficiently clear." No, it wasn't. You have multiple spelling and grammar errors as well as just odd phrasings that make it very diffcult to understand what you are trying to ask.--[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 10:55, 12 September 2024 (UTC)
:::PS- Shantavira's "no, it isn't" was obviously in answer to the question of whether the phrase is an oxymoron.--[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 11:13, 12 September 2024 (UTC)
::::If you could spot my spelling errors than you admit that you knew what the words were that I intended, and thus didn't detract from the readability.
::::I never asked "whether the phrase is an oxymoron", you introduced that question.
::::As I have already said, the amount of effort in "no it isn't" makes your reply completely useless. That reply has NO educational value, it doesn't provide any tools that would enable me to understand an answer to my question, rather you have only encouraged me to blindly copy an answer without understanding anything about the reasons you see for that answer. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:44, 14 September 2024 (UTC)
:::::I for one did not understand the question as you had intended it. I thought that you used ''[[wikt:narcissus|narcissus]]'' as a common noun for a person suffering from [[narcissistic personality disorder]] (although the term is usually used as a synonym of ''[[wikt:Adonis|adonis]]'').  --[[User talk:Lambiam#top|Lambiam]] 18:37, 14 September 2024 (UTC)
:::::You need to explain your concept of "grandiosing" before anyone can give you a satisfactory reply. We don't know what it means so we can't tell where to start. What are some synonyms, how does it trivialize grandiosity (someone's grandiosity? the quality of being grandiose itself?) to attach a name to the word "disorder"? [[User:HansVonStuttgart|HansVonStuttgart]] ([[User talk:HansVonStuttgart|talk]]) 09:52, 16 September 2024 (UTC)
These definitions need to be kept in sight:
[[Narcissus (mythology)|Narcissus]] A fictional character in ancient Greek myth whose self admiration comically exceeded his common sense. We spell Narcissus with a capital first letter for no other reason than that his is a proper name. We derive from Narcissus by analogy (a relationship of resemblence) [[Narcissism|narcissism]] that is a personality style of unusually high preoccupation with oneself and one's own needs. Only when a narcissistic personality is so extreme as to impair mental well-being and [[Psychosocial]] development will it be declared a mental disorder, this called [[Narcissistic personality disorder|narcissistic personality disorder]] (NPD). I see nothing illogical or contradictory in this understanding of NPD. However the OP is here to argue an objection to the term NPD that is difficult to understand and proceeds quite combatively to take issue with every responder to their question.

[[Grandiosity]] is simply an unrealistic sense of unique superiority that is often present in NPD and is in no way a genuine achievement. It is meaningless to talk of grandiosing a third party when grandiosity is only what the NPD feels about themself. The language becomes confused if the real person with NPD is called "narcissus" or "Narcissus" which both seem merely rude. The OP snaps impolitely[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1245003123&oldid=1245000791] at Shantaviraj who actually read the words "achieves grandiosing that person" correctly and attacks Shantaviraj for offering a tentative answer to the unclear question. The OP returning[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1245003434&oldid=1245003123] just 3 minutes later to shore up their own thoughtless contradiction is what I qualify as a snapping behaviour. The OP's next accusation about "Your sneering/snobbery..." is calculated insult. I conclude that despite the best-effort responses from Shantaviraj, Khajidha, Lambiam and HansVonStuttgart this OP is not here to accept any help in the form of references that we could give and that further engagement on the OP's issue is a waste of time. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 12:40, 17 September 2024 (UTC)

:I take "grandiosing" (not an existing word in English, though its formation is transparent) to be an error for '[[wiktionary:aggrandize|aggrandising]]'. {The poster formerly known as 87.81.230.195} [[Special:Contributions/94.6.83.137|94.6.83.137]] ([[User talk:94.6.83.137|talk]]) 14:46, 17 September 2024 (UTC)

== Any observed similarity between [[Hero syndrome]] and [[FDIA]]? ==

I read on the Hero syndrome page.. "The term is used to describe individuals who constantly seek appraisal for valiant or philanthropic acts, especially by creating a harmful situation which they then can resolve". Isn't that very similar to FDIA? There is no mention on the Hero syndrome page of FDIA.

The FDIA page even literally mentions.. "These proxies then gain personal attention and support by taking on this fictitious 'hero role' and receive positive attention from others, by appearing to care for and save their so-called sick child", but doesn't reference the Hero syndrome page either. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:56, 10 September 2024 (UTC)

:A statement such as "A is a kind of B" requires [[WP:V|a reliable source]]. One issue why such sources are hard to come by in this case may be that Factitious Disorder is a recognized disorder (300.19 in [[DSM-5]], F68.1 in [[ICD-10]]), whereas "hero syndrome" is journalese and has no generally accepted diagnostic criteria.  --[[User talk:Lambiam#top|Lambiam]] 17:17, 10 September 2024 (UTC)
::Thank you for the answer. Is there not a lot of literature about hero syndrome? Some of the cases mentioned on the wikipedia page (e.g. a police officer setting a bomb to "be seen defusing it") seem quite high profile, I'd expect to be some literature about that. [[User:Ybllaw|Ybllaw]] ([[User talk:Ybllaw|talk]]) 12:51, 14 September 2024 (UTC)
:::I don't see much that makes the connection, but here is a directly relevant passage in a RS, a book by the title ''The Munchausen Complex: Socialization of Violence and Abuse'':
::::{{tq|In another manifestation of MSBP, a perpetrators will induce a condition in order to heroically “save” the victim thereby showing they are a concerned caretaker. Sometimes health care providers – including nurses of both sexes – do this. Their actions are considered a type of Munchausen Syndrome by Proxy. This phenomenon may very well be a distinct category of Munchausen that should be researched and redefined as Munchausen Malignant Hero Syndrome.}}[https://books.google.com/books?hl=en]
:::The proposal of the last sentence does not appear to have gained traction.  --[[User talk:Lambiam#top|Lambiam]] 18:26, 14 September 2024 (UTC)
:So, I'm going to try to find a good source for this a little later, Ybllaw, but quickly while I am here now: it is worth noting that typically Munchausen by proxy manifests in a desire to derive sympathy and attention from the manufactured ailment, rather than accolades for heroism. That said, I don't think the two pathologies would be by any means mutually exclusive. ''[[User:Snow Rise|SnowRise]][[User talk:Snow Rise| let's rap]]'' 00:33, 22 September 2024 (UTC)

= September 12 =

== Kidney theft ==

Can you tell me something about the kidney theft gangs working out of Southeast Asia? Having a discussion on a forum about them now. [[Special:Contributions/146.200.107.107|146.200.107.107]] ([[User talk:146.200.107.107|talk]]) 23:41, 12 September 2024 (UTC)
:Have you read [[Organ theft]]?-[[User:Gadfium|Gadfium]] ([[User talk:Gadfium|talk]]) 00:53, 13 September 2024 (UTC)
:What kidney theft gangs working out of Southeast Asia are those then? There are so many traffic fatalities in SEAsia that I'm surprised there would be a market for stolen kidneys. [[User:Sean.hoyland|Sean.hoyland]] ([[User talk:Sean.hoyland|talk]]) 04:17, 16 September 2024 (UTC)

= September 14 =

== Atomic electron transition time ==

In Wikipedia article [[Atomic electron transition]] it is written that: "''The time scale of a quantum jump has not been measured experimentally''", why ? [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 12:07, 14 September 2024 (UTC)
:Because nobody knows how to do it (or if they do, they cannot yet implement it in an experiment). An [[attosecond]] is a rather short time. The article lists the shortest laser light pulse created as 43 attoseconds, so that is the shortest time scale that is technically accessible at the moment. But if you have an idea, go for it. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 12:35, 14 September 2024 (UTC)
::There may be a more fundamental reason. Such a measurement would necessarily (I think) require two observations, one essentially being that a some time {{mvar|t}}0 the transition has not yet taken place, the other that at a later time {{mvar|t}}1 the transition has now occurred. Such observations require an [[electromagnetic interaction]], which will unavoidably [[Observer effect (physics)#Particle physics|disturb the observed system]], in particular potentially causing the electron to behave differently. If there is some clever way around this fundamental issue, no one has thought of it.  --[[User talk:Lambiam#top|Lambiam]] 13:07, 14 September 2024 (UTC)
:::Apparently, to date, we do not have the tools precise enough for this measurement. On the other hand, the disturbance of the measurement can be anticipated and circumvented, as in this [https://www.webofscience.com/wos/woscc/full-record/WOS:000289196400005 article] measuring the delay of a photoemission by the 2023 Nobel Prize winner L'Huillier: "''The determination of photoemission time delays requires taking into account the measurement process, involving the interaction with a probing infrared field. This contribution can be estimated using a universal formula and is found to account for a substantial fraction of the measured delay.''" In the past this delay was considered zero, today it is measured around 10 atoseconds. So... [[User:Malypaet|Malypaet]] ([[User talk:Malypaet|talk]]) 21:45, 14 September 2024 (UTC)
::::{{u|Malypaet}}, the imminent development of a practical [[Nuclear clock]], which will be able to measure smaller intervals of time than any possible [[Atomic clock]], may soon enable the precision necessary to measure quantum-jump timescales. {The poster formerly known as 87.81.230.195} [[Special:Contributions/94.6.83.137|94.6.83.137]] ([[User talk:94.6.83.137|talk]]) 14:36, 17 September 2024 (UTC)

== How does one deal with equations with incorrect units? ==

Specifically thinking [https://iopscience.iop.org/article/10.3847/1538-4357/ac779c/pdf this one], equation 31. It doesn't seem to yield a metric unit when you put in some values. [[User:Jo-Jo Eumerus|Jo-Jo Eumerus]] ([[User talk:Jo-Jo Eumerus|talk]]) 16:52, 14 September 2024 (UTC)
:Do you expect us to read and understand the entire paper up to that equation? Maybe you could help us a bit by summarising what the terms stand for, what their units are and why you think the entire equations do not yield "metric" units. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 17:06, 14 September 2024 (UTC)
:It should. All the units in the paper are SI. Script-H in the paper should be heat flux (e.g. conductive thru a 2D surface i.e. an ice sheet), which will be in Joules per second per meter^2. Make sure to write down every step carefully, using the values given in the paper, including the table of constants. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:08, 14 September 2024 (UTC)
::The problem is that the first equation after doing that insertion yields (kg^7*m^11)^(1/10) which is obviously wrong. [[User:JoJo Eumerus mobile|JoJo Eumerus mobile]] ([[User talk:Jo-Jo Eumerus|main talk]]) 18:48, 14 September 2024 (UTC)
:::Ok, I got it to work, to give delta H in meters. The one constant that seemed hidden in the paper was ''b'', but it has the same dimensions as ''b''0 (eqn A2). Also they don't give the [[Coriolis coefficient]] explicitly, but that has rad/sec (1/s) units. Apart from that, all the other constants should be in there. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 19:44, 14 September 2024 (UTC)
::::Is it the [[Coriolis coefficient]] rather than the [[rotation frequency]]? [[User:Jo-Jo Eumerus|Jo-Jo Eumerus]] ([[User talk:Jo-Jo Eumerus|talk]]) 09:02, 15 September 2024 (UTC)
:::::Yes, as defined after Eq. (10) of the paper, ''f'' represents the [[Coriolis coefficient]], which is subsequently used in Eq. (31). [[User:Nanosci|Nanosci]] ([[User talk:Nanosci|talk]]) 16:30, 15 September 2024 (UTC)

= September 15 =

== the dual of polydactyly ==

[[Polydactyly]] happens. But do people ever grow a finger with an extra joint? [[User:Tamfang|—Tamfang]] ([[User talk:Tamfang|talk]]) 05:44, 15 September 2024 (UTC)
:Googling ''finger with an extra joint'' the first hit is our very own article [[Triphalangeal thumb]]. The first page of search results only mentions an extra crease on the little finger, with no underlying extra bones. But scroll down on the results, maybe you'll get lucky! [[Special:Contributions/85.76.83.87|85.76.83.87]] ([[User talk:85.76.83.87|talk]]) 14:54, 15 September 2024 (UTC)

== Gull with injured foot ==

Take a look at [https://youtube.com/shorts/NZZ5fHKz4xE?si=F0plWRF9SYIbThAJ this video] from a YouTube channel I follow. Steven the seagull injured her (yeah, Steven turned out to be female, but the name stuck anyway) foot somehow. Accident, fight, attack by a predator - whatever happened, the webbing between her toes got split. Does anyone know if that will grow back eventually? [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 21:44, 15 September 2024 (UTC)

:From {{slink|Regeneration (biology)#Aves (birds)}}: {{tq|Owing to a limited literature on the subject, birds are believed to have very limited regenerative abilities as adults.}} I was able to find [http://www.majesticwaterfowl.org/mmissue30.htm an issue of a waterfowl newsletter] with a picture of a duck's foot webbing, apparently torn and partially regrown. Based on this, I think it's very likely to grow back ''somewhat'', but perhaps less likely to grow back ''completely''. I'm rooting for Steven though! [[User:Jlwoodwa|jlwoodwa]] ([[User talk:Jlwoodwa|talk]]) 01:52, 16 September 2024 (UTC)
::She's been getting her foot doused with antiseptic and eats a REALLY good diet for an urban gull (fresh fish, fresh meat, mealworms daily), so she's in a better position than most. [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 13:37, 16 September 2024 (UTC)
:Presumably it could only heal if the split was mechanically sealed first. If the surfaces keep moving relative to each other or they get dirty I don't see how the split can heal. [[User:Shantavira|Shantavira]]|[[User talk:Shantavira|feed me]] 08:23, 16 September 2024 (UTC)
::Reminds me of [[Paul Temple]]'s wife! [[Special:Contributions/2A00:23C5:E161:9200:D500:7967:3BC2:6E0B|2A00:23C5:E161:9200:D500:7967:3BC2:6E0B]] ([[User talk:2A00:23C5:E161:9200:D500:7967:3BC2:6E0B|talk]]) 10:04, 16 September 2024 (UTC)
::I was thinking that it might grow back from the bottom outwards. Not really sure how it works in gulls, compared to us, if we split that thin bit of flesh between thumb and forefinger. [[User:Iloveparrots|Iloveparrots]] ([[User talk:Iloveparrots|talk]]) 13:34, 16 September 2024 (UTC)
:::My experience with wildlife rehabilitation, including occasional avians and waterfowl, but not gulls, suggests to me that it will not substantially regrow. In most animals with thin membranes of this sort, post-developmental regeneration is extremely limited once the semi-vascularized tissues are torn; the cells are of differentiated types which simply are not capable of interacting in the manner necessary to reconstruct the overall structure, instead prioritizing more localized closure of the wound site. In short, Steven will probably see an uneven healing pattern around the periphery of the torn segment with some thick scarification. I wouldn't expect more than 5-10% of the gap to fill. {{pb}} That said, while webbing is obviously a helpful adaptation for gulls, tears of this sort are not uncommon and typically not life threatening (either through initial infection or dehabilitation). Considering that Steven seems to have a much more robust support network than your average gull and lives in sheltered semi-urban, semi-natural conditions, she can probably be expected to have a fair long life by gull standards. Please feel free to update me about the foot if my conjecture proves wrong: I'd be interested in the outcome. ''[[User:Snow Rise|SnowRise]][[User talk:Snow Rise| let's rap]]'' 00:22, 22 September 2024 (UTC)

= September 18 =

== Is there any physical theory, claiming that every elementary particle can turn into some other elementary particle? ==

[[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 13:05, 18 September 2024 (UTC)

:[[Quark]]s are the only known particles whose electric charges are not [[integer]] multiples of the [[elementary charge]]. Therefore, in physical theories that accept both the [[Standard Model]] and the [[law of charge conservation]], a quark cannot turn into another particle but a quark. But the types of quarks all have different masses, so all such quark–quark changes violate the [[law of conservation of mass]].  --[[User talk:Lambiam#top|Lambiam]] 17:57, 18 September 2024 (UTC)
::If you are referring to a single elementary particle, so why didn't you mention the electron, besides the quark?
::If that's because an electron colliding with a positron turns (together with the positron) into a pair of photons, then also a quark colliding with an anti-quark turns (together with the anti-qurk) into a pair of gluons.
::Anyway, in my question I allow a given elementary particle to collide with its anti-matter for becoming another elementary particle.
::More important: My question is theoretical, so it's not only about known particles, but rather about all possible particles, including those which haven't been discovered yet. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 18:21, 18 September 2024 (UTC)
:::If someone claims all swans are white, it suffices to debunk the claim by finding one purple swan. Maybe there also blue, brown or black swans, but it is not necessary to search for further counterexamples. Likewise, if some physical theory claims every elementary particle can turn into some other elementary particle, it suffices to debunk the claim by finding just one elementary particle that cannot turn into some other elementary particle. I just started with the top line of [[:File:Standard Model of Elementary Particles.svg]]. There may be many other counterexamples (like the [[Higgs boson]]), but why bother to keep searching?
:::The as of yet undiscovered bunkon and trashon, whose properties are still unknown except that they are postulated to be different elementary particles, can turn into each other. A difficulty in finding them is that their properties are unknown, so experimental physicists don't know where to look. There may be many more such pairs, which may never be discovered.  --[[User talk:Lambiam#top|Lambiam]] 10:17, 19 September 2024 (UTC)
::::By mistake, I thought you meant the quark was the only particle that couldn't turn into another particle but a quark, but now I see this was not what you meant, so I take my first sentence back.
::::However, I still emphasize that my question allows a given elementary particle to collide with its anti-matter for becoming another elementary particle.
::::Re. your senetnce: "The as of yet undiscovered...different elementary particles, can turn into each other": Is there any physical theory claiming what you've claimed in that sentence? Actually, this was my original question... [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:44, 19 September 2024 (UTC)
:::::I'm pretty sure that that sentence was a joke. Look at the names: BUNKon and TRASHon. --[[User:Khajidha]] ([[User talk:Khajidha|talk]]) ([[Special:Contributions/Khajidha|contributions]]) 11:25, 19 September 2024 (UTC)
::::::No "maybe" about black swans. They were recorded by Europeans in [[Swan River Colony|1697]], possibly earlier. [[Special:Contributions/2A00:23D0:F6F:1001:2D07:A712:8909:7D91|2A00:23D0:F6F:1001:2D07:A712:8909:7D91]] ([[User talk:2A00:23D0:F6F:1001:2D07:A712:8909:7D91|talk]]) 11:56, 19 September 2024 (UTC)
::::::All right. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:35, 19 September 2024 (UTC)
::::::: See also [[black swan]] and [[black swan theory]]. -- [[User:JackofOz|Jack of Oz]] [[User talk:JackofOz#top|[pleasantries]]] 18:37, 19 September 2024 (UTC)

::OP may have in mind something more like the particles created from particle-antiparticle annihilation, such as those in the chart at {{slink|Annihilation#Electron%E2%80%93positron_annihilation}}, as opposed to something like the weak decay of quarks.
::It seems to me that OP could mean either: 1) a single elementary particle can spontaneously become another single elementary particle (with the help of another particle that remains unchanged), in which case I think the answer may be no for any particle; or 2) for two given particles, there's an interaction in some condition where it's meaningful to say that one specified particle is in the input, and it becomes in the output the other specified particle [Edit: which may include any number of other particles in the reaction doing anything else]. Not sure (I didn't do particle), but I think (2) might be considered more or less accurate (to the extent the fuzziness of the wording necessarily allows). [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 16:10, 19 September 2024 (UTC)
:::I adopt your option 1# if it means [[Particle decay]], and I adopt your option 2# if it means [[annihilation]] (i.e. by colliding with the anti-particle).
::::
:::But contrary to the way you divided you answer: option 1# for '''all''' particles, or option 2# for '''all''' particles, I didn't exclude a third option which is: option 1# for '''some''' particles, and option 2# for the '''rest''' of the particles (without excluding particles that satisfy both 1# and 2#).
::::
:::All agree, that some particles satisfy option 1#, and that some particles satisfy option 2#.
::::
:::My question is about whether there is any physical theory claiming, that every particle (including any particle that hasn't been discovered yet), satisfies either 1# or 2# (or both). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:25, 20 September 2024 (UTC)
::::I was trying to interpret your question literally. #1 is one single particle becoming one different single particle with everything else unchanged -- this does not happen at all afaik, nor in general in theory ([[User:Lambian]] gives a simple example for quarks in their answer above). #2, the way I worded it, afaik can (and does) happen for all particles in the Standard Model.
::::What I'm trying to convey with this #1/#2 description is that it's not a particularly meaningful one, if you can claim "every elementary can turn into some other elementary particle" just by comparing one reactant to one product in a complex interaction.
::::(As maybe a sorta-ok example, consider the chemical reaction of a strong acid + base into salt + water: HCl + NaOH -> NaCl + H2O. Would you say the HCl (reactant) turns into salt? turns into water? Or does it change nothing at all because both the reactants and products are largely remain just free ions in aqueous solution? This is why I'm not sure what you're trying to ask is very meaningful.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 17:24, 20 September 2024 (UTC)
:::::I'm '''not''' asking about a single particle becoming one different single particle with everything else unchanged. Let's put it this way: Is there any physical theory claiming that all particles in the [[dark matter]] can turn into other particles? (whether by a decay or by annihilation or by any other way). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 01:30, 22 September 2024 (UTC)
::::::There can never be such a theory. Why? Dark matter is named so because it never interacts with ordinary matter, except by gravity. As soon as it interacts in any other way it's not dark matter anymore but a new kind of ordinary matter. By interaction by gravity no distinction of particles is possible, only sum and distribution of mass is measurable. So dark matter can decay all it want, no human physicists are able to prove it or disprove it. By definition of the word. It may be that some particles, that we now subsume in dark matter, are later discovered to be not dark. And then we would know the conditions where they participate in the normal decay of ordinary matter. But that can never tell us about the real dark matter, as long as there's real dark matter. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 18:20, 23 September 2024 (UTC)
:::Most particles [[Particle decay|decay]] into other particles. The only "stable" ones are [[Electron]]s, [[Proton]]s, [[Photon]]s and (to a degree [[Neutrino oscillation|(see here)]]) [[Neutrino]]s. But even these can (under the right conditions) either [[Electron capture|combine]] or [[Photoelectric effect|"destroy"]] and [[Spontaneous emission|"create"]] with each other. [[Special:Contributions/176.0.165.39|176.0.165.39]] ([[User talk:176.0.165.39|talk]]) 12:20, 20 September 2024 (UTC)
::::These [[Fundamental interaction|interaction]]s can all be depicted in a [[Feynman diagram]] as lines meeting in a vertex. The lines correspond to particles. In a Feynman diagram, a vertex is always the meeting point of three lines. A particle → particle change would correspond to a Feynman diagram in which just two lines meet in a vertex.  --[[User talk:Lambiam#top|Lambiam]] 22:47, 20 September 2024 (UTC)
:::::Or two lines merging in two vertices that are connected by two lines in the form looking like an eye. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 14:24, 23 September 2024 (UTC)
::::Yes, I know that. but you're talking about partciles of the Standard Model, while I'm asking about a theory that claims that '''all''' particles, including those which '''haven't been discovered yet''', can <s>decay</s> turn into other particles. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 01:30, 22 September 2024 (UTC)
:::::In your question and first response you talked about a particle that "can turn into some other elementary particle", and people are trying to clarify what that can mean. But now you're asking about decay: "[[Particle decay]]" is where ''only one'' particle goes in, and some other number of different particles come out, but as others have said there are stable particles that do not decay. (There are of course experimental bounds to what we currently know of this, and there are interesting subtleties in the [https://arxiv.org/pdf/1304.2821 theory for example why a photon does not decay].)
:::::There's no theory which can claim anything meaningful about all particles that have not been discovered yet. A theory predicts new particles, and the theory becoming successful may lead to building experiments to verify empirically the particles ("discover" them, although a "discovery" was equally done when the theory was written).
:::::You could imagine another type of theory that might say all particle physics theories are really at a fundamental level part of X-theory, and in X-theory everything decays into X-dust in 20 billion years, but that's not a particle theory. [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 05:48, 22 September 2024 (UTC)
::::::Re. your first paragraph: I'm sorry for not being clear in my recent response. Thanks to your comment, I will make it clearer, as I've alraedy made it in my first post.
::::::Re. your second paragraph: I mean, something like the [[supersymmetric theory]], claiming something about all particles, including those which haven't been discovered yet. So, again, I'm asking whether there's a theory that claims that all particles, including those which haven't been discovered yet, can <s>decay</s> '''turn''' into other particles, whether by a '''[[particle decay|decay]]''' or by '''annihilation''' or by any other way. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:45, 22 September 2024 (UTC)
Although the above discussion may imply that the words "hypothesis" and "theory" can be used interchangeably, a scientific hypothesis is not the same as a scientific theory.

An answer is '''No''', there is no scientific theory that just claims anything. A [[Scientific theory|scientific theory]] offers a generalized explanation of how [[Nature (philosophy)|nature]] works described in such a way that scientific tests should be able to provide [[Empirical evidence|empirical]] support for it, or [[Empirical evidence|empirical]] contradiction ("[[Falsifiability|falsify]]") of it.

The OP's question using the word "theory" to mean a claim that at best will remain unproven or speculative actually looks for a [[Hypothesis]] meaning an educated guess or thought about something that cannot satisfactorily be explained with the present scientific theories. The OP seems to be thinking aloud[https://en.wikipedia.org/w/index.php?title=Wikipedia%3AReference_desk%2FScience&diff=1246958875&oldid=1246954714] a new hypothesis. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 10:37, 22 September 2024 (UTC)
:See [[Supersymmetric theory]]. It claims something about all particles, including those which haven't been discovered yet, and it's still called a "theory". Anyway, I'm not focusing on terminology but rather on an idea: Is there any theory, or a well known hypothesis, or a well known conjecture, or whatever, claiming that all particles, including those which haven't been discovered yet, can turn into other particles, whether by a '''[[particle decay|decay]]''' or by '''annihilation''' or by any other way. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 12:45, 22 September 2024 (UTC)
::Wikipedia editors are careful about terminology. By "Supersymmetric theory" you link to the article titled [[Supersymmetry]]. Its first line clarifies that it refers not to a theory but a theoretical framework. Read further to see how it anticipates what might characterise a supersymmetry theory without specifying any one for attention. Merely calling a supposed bosonic superpartner to the electron a selectron hardly amounts to a falsifiable hypothesis and obviously says nothing about undiscovered particles. Beside our care with terminology, we are not in the business of prediction. [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 09:17, 23 September 2024 (UTC)
:::I've linked to our article [[Supersymmetric theory]], which does exist in Wikipedia, so when I used the term "supersymmetic theory" I used a term used in Wikipedia as well. Indeed, it passes to the article [[Supersymmetry]], but also this article does point out - in its second paragraph - that {{tq|"Dozens of supersymmetric theories exist"}}, whereas the first paragraph of this article - does point out that the suppersymmetry {{tq|"proposes that for every known particle, there exists a partner particle with different spin properties. There have been multiple experiments on supersymmetry that have failed to provide evidence that it exists in nature."}}
:::Anyway, my original question was not about the terminology used in Wikipedeia, but rather about the very idea, and I allow you to call it: theory, theoretical framework, hypothesis, conjecture, proposal, suggestion, idea, or whatever, but the main idea still remains, as long as I understand you and you understand me (I guess this is the case). [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:07, 23 September 2024 (UTC)
::Now you only have to define what you mean by particle. For instance in [[Standard Model]] you have the everyday particles ([[Electron]],[[Proton]]...). Nothing of that is stable in your definition. Then you have [[Quark]]. No quarks are ever single. So it is a question of the neighbouring quarks which reactions are possible. But even then there is no stability in your definition. But never is one particle turned into exactly one other particle. Even if that were possible you only have to look at a different level of abstraction and a group of particles would turn into a different group of particles. [[Special:Contributions/176.0.158.114|176.0.158.114]] ([[User talk:176.0.158.114|talk]]) 09:34, 23 September 2024 (UTC)
:::By elementary partice I mean what physicists mean by that term: quarks, leptons, gauge bosons, and also elementray particles that haven't been discovered yet, like axions. Anyway, I really meant what you suggested in yout last sentence: "a group of [elementray] particles would turn into a different group of [elementray] particles". [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 10:07, 23 September 2024 (UTC)
::::Then I can give you a definite answer. Any group of ordinary matter particles (whether known or not) can turn into another group of particles if they encounter the right conditions (even if the conditions could not be achieved in a laboratory or somewhere near Earth). For dark matter particles that can not scientifically be said. And never will be possible to say with science. If someone says something about changing about dark matter it is and never will be science. That is part of the definition of the word "dark" in "dark matter". If that definition changes nothing about the future I have written will continue to be valid. [[Special:Contributions/176.0.153.105|176.0.153.105]] ([[User talk:176.0.153.105|talk]]) 19:28, 23 September 2024 (UTC)
:::::Memorandum: My question was about '''all''' elementary particles, and by elementary partice I mean what physicists mean by that term: quarks, leptons, gauge bosons, and also elementray particles that haven't been discovered yet, like axions.
:::::To sum up: The question is whether, for every group of elementary particles, including those which haven't been discovered yet, '''there exist (what you call) "right conditions"''', under which this group can turn into another group of elementary particles. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 13:10, 24 September 2024 (UTC)
::::::Then as I said all the way before, with my "#2", then if it can be called a "particle", yes you can always make it turn into stuff.
::::::But you should understand what people here are trying to say: this becomes rather meaningless as your understanding of what a theory means, in the sense of the "discovery" of particles, is not very accurate, so when you're trying to force these incompatible notions into your question it makes it difficult to give meaningful answers. (Mine, as I said before, is not particularly meaningful.) [[User:SamuelRiv|SamuelRiv]] ([[User talk:SamuelRiv|talk]]) 13:28, 24 September 2024 (UTC)
:::::::Theories don't necessarily discuss discoveries, and a theory about elementary paricles doesn't necessarily discuss what you call "discovery" of elementary paricles, it can also say something about elementary paricles that haven't been discovered yet, e.g. gravitons, axions, electrinos, gravitinos, axinos, and the like. Anyway, my question is about all elementary particles, including those which haven't been discovered yet. Are you referring to all of them in your first sentence? [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 18:26, 24 September 2024 (UTC)

= September 21 =

== Variables in chemistry?! ==

I've seen the symbols '''M''' and '''X''' in chemistry, what do they mean? [[User talk:Hydrogen astatide|H]][[User:Hydrogen astatide|At]] 04:07, 21 September 2024 (UTC)
:Well M could represent a metal, and X could represent a [[halogen]] in a chemical formula, eg NaX could be a halide salt of sodium. X is probably F, Cl, Br or I. Theoretically it could be At, but not in any visible amount. If the symbols are in italic text they may represent a number. [[User:Graeme Bartlett|Graeme Bartlett]] ([[User talk:Graeme Bartlett|talk]]) 06:04, 21 September 2024 (UTC)

= September 22 =

== [[B-boson]] ==

Besides a link to our article [[electroweak interaction]] that mentions the [[B-boson]] without telling anything about it, we have no article about this boson. Why?

I'm eager to know some basic data about it, e.g. mass, electric charge, spin, isospin, stability, experiments trying to detect it, and likewise. But... nothing? [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 16:27, 22 September 2024 (UTC)
:<s>You'll find it at [[B meson]].</s> Sorry, although the B meson is a boson, it is not the beast that's mentioned in [[electroweak interaction]]. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 17:23, 22 September 2024 (UTC)
::What a pity. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 08:57, 23 September 2024 (UTC)
::The B-boson isn’t a well-known particle in the standard model of particle physics. Are you thinking of the [[Higgs boson]] that was discovered in 2012? [[User:Philvoids|Philvoids]] ([[User talk:Philvoids|talk]]) 08:47, 23 September 2024 (UTC)
:::No, I'm looking for basic data (e.g. mass charge spin isospin parity etc.) of the B-boson mentioned in our article [[electroweak interaction]]. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 08:57, 23 September 2024 (UTC)
::::The thing is that the B boson doesn't exist as an entity in our Universe. It "exists" before symmetry breaking, but since our world has a broken symmetry the observable bosons are the Z0 and the photon instead of the W3 and B. As the B cannot be observed, many of your questions are moot. --[[User:Wrongfilter|Wrongfilter]] ([[User talk:Wrongfilter|talk]]) 09:07, 23 September 2024 (UTC)
:::::Got it. [[User:HOTmag|HOTmag]] ([[User talk:HOTmag|talk]]) 09:31, 23 September 2024 (UTC)

= September 24 =

== Cloning the Carolina parakeet ==

In theory, would it be possible to clone the extinct [[Carolina parakeet]] by taking whatever existing DNA we have of the species and filling any gaps with DNA from the [[sun conure]] (closest living relative and very common pet) and then putting that into a sun conure egg? I have read that it's very difficult to clone birds though. [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 23:12, 24 September 2024 (UTC)
:Here's an Audubon Magazine [https://www.audubon.org/news/what-would-happen-if-we-brought-birds-back-dead write up] on the topic. It foolishly says that the Carolina parakeet, [[ivory-billed woodpecker]], and [[passenger pigeon]] could be invasive, which is nonsense; only the Carolina parakeet could conceivably be successful beyond its former range. See [[monk parakeet]] for why. [[User:Abductive|'''Abductive''']] ([[User talk:Abductive|reasoning]]) 23:55, 24 September 2024 (UTC)
::Yes, there's been a lot of talk about removing monk parakeets from areas where they are non-native. But the public tend to get extremely angry about the idea of culling parrots specifically, even to the point of taking direct action when nests are removed. I believe there was even a politician a few years ago who said something along the lines of "absolutely not" when it came to the idea of removing that species being raised by his advisors. [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 00:19, 25 September 2024 (UTC)

:Would you then get an actual Carolina parakeet, or merely a hybrid that kind of looks like it? ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 01:30, 25 September 2024 (UTC)
::Yes, I was thinking that myself. How much of the Carolina parakeet's DNA can be replaced by another (very closely related) species before it can no longer be considered a Carolina parakeet? [[Special:Contributions/146.200.126.178|146.200.126.178]] ([[User talk:146.200.126.178|talk]]) 01:42, 25 September 2024 (UTC)
:::Has the genome of any of these extinct species been mapped? I don't think the article says. But that would be a way to maybe get closer to a real clone. And I understand what they mean by invasive. If a species wasn't someplace, and then appears in that place, by definition it's invasive. That doesn't necessarily mean it will be harmful to other species in that place, but it could be. ←[[User:Baseball Bugs|Baseball Bugs]] ''[[User talk:Baseball Bugs|What's up, Doc?]]'' [[Special:Contributions/Baseball_Bugs|carrots]]→ 07:18, 25 September 2024 (UTC)

= September 25 =
== Etymology of wheldone ==
What is the etymology of wheldone? The references {{doi|10.1021/acs.orglett.0c00219}} and {{doi|10.1021/acs.jnatprod.4c00649}} only described the chemical as a fungal metabolite isolated from the coculture of Aspergillus fischeri and Xylaria flabelliformis. --[[User:Leiem|Leiem]] ([[User talk:Leiem|talk]]) 09:00, 25 September 2024 (UTC)

Pentaerythritol tetranitrate

2024-09-18T09:08:30Z

Leiem: /* Properties */ add missing template parameter

{{Short description|Explosive chemical compound}}
{{redirect|PETN|the wind power station| Taiba N'Diaye Wind Power Station}}
{{pp-extended|small=yes}}
{{Use mdy dates|date=November 2015}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 477001336
| Name =
| ImageFile =
| ImageFile1 = PETN.svg
| ImageAlt1 = Skeletal formula
| ImageFile2 = PETN-from-xtal-2006-3D-balls-B.png
| ImageAlt2 = Ball-and-stick model
| ImageFile3 = Pentaerythritol tetranitrate 05.jpg
| ImageAlt3 = Pentaerythritol tetranitrate after crystalization from acetone
| ImageSize3 = 235px
| PIN = 2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate
| SystematicName =
| OtherNames = [3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
| IUPACName =
| Section1 = {{Chembox Identifiers
| CASNo = 78-11-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 10L39TRG1Z
| PubChem = 6518
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6271
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 466659
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TZRXHJWUDPFEEY-UHFFFAOYSA-N
| SMILES = C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
| InChI = InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
}}
| Section2 = {{Chembox Properties
| C=5 | H=8 | N=4 | O=12
| Appearance = White crystalline solid<ref name=epa1>{{Cite journal|url=https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-url=https://web.archive.org/web/20240801034435/https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-date=2024-08-01 |url-status=live|title=Provisional Peer-Reviewed Toxicity Values for Pentaerythritol Tetranitrate (PETN) (CASRN 78-11-5)|date=July 2021|publisher=United States Environmental Protection Agency |journal=Provisional Peer-Reviewed Toxicity Values}}</ref>
| MolarMass = 316.137 g/mol
| Density = 1.77 g/cm3 at 20 °C
| MeltingPtC = 141.3
| BoilingPtC = 180
| BoilingPt_notes = (decomposes above {{convert|150|C|F}})
| Solubility =
}}
| Section3 = {{Chembox Explosive
| ShockSens = Medium
| FrictionSens = Medium
| DetonationV = 8400 m/s (density 1.7 g/cm3)
| REFactor = 1.66}}
| Section4 = {{Chembox Hazards
| GHSPictograms = {{GHS06}} {{GHS01}} {{GHS health hazard}}
| GHSSignalWord = '''Danger'''
| HPhrases = {{H-phrases|201|302|316|370|373|241}}
| PPhrases = {{P-phrases|210|250|261|264|301+312|372|401|501|370+380}}
| NFPA-F = 1
| NFPA-H = 2
| NFPA-R = 3
| FlashPt =
| AutoignitionPtC = 190
}}
| Section5 = {{Chembox Pharmacology
| ATCCode_prefix = C01
| ATCCode_suffix = DA05
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
}}
| Section6 =
}}

'''Pentaerythritol tetranitrate''' ('''PETN'''), also known as '''PENT''', '''pentyl''', '''PENTA''' ('''''ПЕНТА''''', primarily in Russian), '''TEN''' (tetraeritrit nitrate), '''corpent''', or '''penthrite''' (or, rarely and primarily in German, as '''''nitropenta'''''), is an [[explosive]] material. It is the [[nitrate ester]] of [[pentaerythritol]], and is structurally very similar to [[nitroglycerin]]. [[Penta-|Penta]] refers to the five [[carbon atom]]s of the [[neopentane]] skeleton. PETN is a very powerful explosive material with a [[relative effectiveness factor]] of 1.66.<ref name="urlPETN [Pentaerythritol tetranitrate]">{{cite web |url= http://www.globalsecurity.org/military/systems/munitions/explosives-nitrate-petn.htm |title=PETN (Pentaerythritol tetranitrate) |access-date=March 29, 2010}}</ref> When mixed with a [[plasticizer]], PETN forms a [[plastic explosive]].<ref>{{cite encyclopedia |title = Explosives |encyclopedia = A dictionary of military history and the art of war |last= Childs |first= John |url = https://books.google.com/books?id=nEQ7FUAdmc8C&pg=PA231 |format = [[Google Books]] extract |isbn = 978-0-631-16848-5 |year = 1994}}</ref> Along with [[RDX]] it is the main ingredient of [[Semtex]].

PETN is also used as a [[Vasodilation|vasodilator]] drug to treat certain heart conditions, such as for management of [[angina]].<ref name = newdrugs>{{cite journal |pmc = 1831125 |title = New Drugs |journal = [[Can Med Assoc J]] |year = 1959 |volume = 80 |pages = 997–998 |pmid=20325960 |issue=12}}</ref><ref name = ebadi>{{cite book |title = CRC desk reference of clinical pharmacology |page = 383 |author = Ebadi, Manuchair S. |year = 1998 |publisher = CRC Press |isbn = 978-0-8493-9683-0 |url = https://books.google.com/books?id=-EAxShTKfGAC&pg=PA383 |format = [[Google Books]] excerpt}}</ref>

==History==
Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer {{Interlanguage link|RWS (company)|lt=Rheinisch-Westfälische Sprengstoff A.G.|de|RWS (Unternehmen)}} of [[Cologne|Cologne, Germany]].<ref>Deutsches Reichspatent 81,664 (1894)</ref><ref>Thieme, Bruno [http://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541,899.PN.%2526OS%3DPN%2F0541,899%2526RS%3DPN%2F0541,899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page "Process of making nitropentaerythrit,"] {{Webarchive|url=https://web.archive.org/web/20210711151323/https://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541%2C899.PN.%2526OS%3DPN%2F0541%2C899%2526RS%3DPN%2F0541%2C899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page |date=July 11, 2021 }} U.S. patent no. 541,899 (filed: November 13, 1894; issued: July 2, 1895).</ref><ref>Krehl, Peter O. K. (2009) ''History of Shock Waves, Explosions and Impact''. Berlin, Germany: Springer-Verlag. [https://books.google.com/books?id=PmuqCHDC3pwC&pg=PA405 p. 405].</ref><ref>Urbański, Tadeusz; Ornaf, Władysław and Laverton, Sylvia (1965) ''Chemistry and Technology of Explosives'', vol. 2 (Oxford, England: Permagon Press. [https://archive.org/stream/ChemistryAndTechnologyOfExplosives-VolumeIi/ChemistryAndTechnologyOfExplosives-VolumeIi-TadeuszUrbanski#page/n183/mode/2up p. 175.]
</ref> The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military in {{nowrap|[[World War I]]}}.<ref>German Patent 265,025 (1912)</ref><ref>{{cite book|title = Die Schiess- und Sprengstoffe|author = Stettbacher, Alfred |place = Leipzig |publisher= Barth|year = 1933| page= 459| edition = 2. völlig umgearb. Aufl. }}</ref> It was also used in the [[MG FF cannon|MG FF/M autocannons]] and many other weapon systems of the [[Luftwaffe]] in World War II.{{cn|date=September 2024}}

==Properties==
PETN is practically [[solubility|insoluble]] in water (0.01 g/100 mL at 50 °C), weakly soluble in common nonpolar [[solvent]]s such as [[Aliphatic compound|aliphatic hydrocarbon]]s (like gasoline) or [[Carbon tetrachloride|tetrachloromethane]], but soluble in some other organic solvents, particularly in [[acetone]] (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and [[dimethylformamide]] (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). It is a non-planar molecule that crystallizes in the space group ''P''{{overline|4}}21''c''.<ref>{{cite journal|author=Zhurova, Elizabeth A.; Stash, Adam I.; Tsirelson, Vladimir G.; Zhurov, Vladimir V.; Bartashevich, Ekaterina V.; Potemkin, Vladimir A.; Pinkerton, A. Alan|year=2006|title=Atoms-in-Molecules Study of Intra- and Intermolecular Bonding in the Pentaerythritol Tetranitrate Crystal|journal=Journal of the American Chemical Society|volume=128|issue=45|pages=14728–14734|doi=10.1021/ja0658620}}</ref> PETN forms [[eutectic system|eutectic]] mixtures with some liquid or molten [[aromaticity|aromatic]] [[nitro compound]]s, ''e.g.'' [[trinitrotoluene]] (TNT) or [[tetryl]]. Due to steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemical [[reagent]]s; it does not [[hydrolysis|hydrolyze]] in water at room temperature or in weaker [[alkalinity|alkaline]] [[aqueous solution]]s. Water at 100 °C or above causes [[hydrolysis]] to dinitrate; presence of 0.1% [[nitric acid]] accelerates the reaction.

The [[chemical stability]] of PETN is of interest, because of the presence of PETN in aging weapons.<ref>{{Cite tech report | title = Aging of Pentaerythritol Tetranitrate (PETN) | url = https://www.osti.gov/servlets/purl/966904 | last = Foltz | first = M. F. | institution = [[Lawrence Livermore National Laboratory]] | date = July 27, 2009 | number = LLNL-TR-415057 | osti = 966904 | access-date = May 14, 2023 }}</ref> [[Neutron radiation]] degrades PETN, producing [[carbon dioxide]] and some pentaerythritol dinitrate and [[Nitrate|trinitrate]]. [[Gamma radiation]] increases the [[thermal decomposition]] sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary [[Chemical decomposition|degradation]] mechanism is the loss of [[nitrogen dioxide]]; this reaction is [[autocatalytic]].{{Citation needed|date=November 2010}} Studies were performed on [[thermal decomposition]] of PETN.<ref>German, V.N. et al. [http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf Thermal decomposition of PENT and HMX over a wide temperature range] {{Webarchive|url=https://web.archive.org/web/20200410211224/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf |date=April 10, 2020 }}. Institute of Physics of Explosion, RFNC-VNIIEF, Sarov, Russia</ref>

In the environment, PETN undergoes [[biodegradation]]. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.<ref>{{Cite journal|last1=Zhuang|first1=Li|last2=Gui|first2=Lai|last3=Gillham|first3=Robert W.|date=2012-10-01|title=Biodegradation of pentaerythritol tetranitrate (PETN) by anaerobic consortia from a contaminated site|url=http://www.sciencedirect.com/science/article/pii/S0045653512005942|journal=Chemosphere|language=en|volume=89|issue=7|pages=810–816|doi=10.1016/j.chemosphere.2012.04.062|pmid=22647196|bibcode=2012Chmsp..89..810Z|issn=0045-6535}}</ref> PETN has low [[Volatility (chemistry)|volatility]] and low solubility in water, and therefore has low [[bioavailability]] for most organisms. Its [[toxicity]] is relatively low, and its [[transdermal]] absorption also seems to be low. It poses a threat for aquatic [[organism]]s. It can be degraded to pentaerythritol by [[iron]].<ref>{{cite journal|doi=10.1021/es7029703|title=Degradation of Pentaerythritol Tetranitrate (PETN) by Granular Iron|journal=[[Environ. Sci. Technol.]]|year=2008|volume=42|pages=4534–9|pmid=18605582|issue=12|last1=Zhuang|first1=L|last2=Gui|first2=L|last3=Gillham|first3=R. W.|bibcode=2008EnST...42.4534Z}}</ref>

==Production==

Production is by the reaction of [[pentaerythritol]] with concentrated [[nitric acid]] to form a precipitate which can be recrystallized from acetone to give processable crystals.<ref name = Ullmann>{{Ullmann | doi = 10.1002/14356007.a10_143.pub2 | title = Explosives | author = Boileau, Jacques | author2 = Fauquignon, Claude | author3 = Hueber, Bernard | author4 = Meyer, Hans H. | name-list-style=amp }}</ref>

Variations of a method first published in US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) form the basis of all current commercial production.{{cn|date=September 2024}}

PETN is manufactured by numerous manufacturers as a powder, or together with [[nitrocellulose]] and [[plasticizer]] as thin plasticized sheets (e.g. [[Primasheet]] 1000 or [[Detasheet]]). PETN residues are easily detectable in hair of people handling it.<ref>Winslow, Ron. (December 29, 2009) [https://www.wsj.com/articles/SB126195987401406861 A Primer in PETN – WSJ.com]. ''The Wall Street Journal''. Retrieved 2010-02-08.</ref> The highest residue retention is on black hair; some residues remain even after washing.<ref>{{cite journal | last1 = Oxley | first1 = Jimmie C. | last2 = Smith | first2 = James L. | last3 = Kirschenbaum | first3 = Louis J. | last4 = Shinde | first4 = Kajal. P. | last5 = Marimganti | first5 = Suvarna | title = Accumulation of Explosives in Hair | journal = Journal of Forensic Sciences | volume = 50 | issue = 4 | year = 2005 | pages = 826–31 | doi = 10.1520/JFS2004545| pmid = 16078483 }}</ref><ref name="latimes.com">{{cite news| url=https://www.latimes.com/archives/la-xpm-2010-nov-24-la-na-petn-20101124-story.html |title= PETN: The explosive that airport security is targeting |last=Bennett |first=Brian |agency=Tribune Washington Bureau |date=November 24, 2010 |work=Los Angeles Times |access-date=July 19, 2015}}</ref>

==Explosive use==

[[File:Pentryt.jpg|thumbnail|Pentaerythritol tetranitrate before crystallization from acetone]]

The most common use of PETN is as an explosive with high [[brisance]]. It is a [[secondary explosive]], meaning it is more difficult to detonate than [[primary explosive]]s, so dropping or igniting it will typically not cause an explosion (at [[standard atmospheric pressure]] it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such as [[TNT]] or [[tetryl]].<ref name = Ullmann/><ref name=nyt>{{Cite news|url=https://www.nytimes.com/2009/12/28/us/28explosives.html?ref=us|title=Explosive on Flight 253 Is Among Most Powerful |newspaper=The New York Times|date=December 27, 2009|author=Chang, Kenneth }}</ref> Under certain conditions a [[deflagration to detonation transition]] can occur, just like that of [[ammonium nitrate]].

It is rarely used alone in military operations due to its lower stability, but primarily used in main charges of plastic explosives such as [[C-4 (explosive)|C4]] along with other explosives (especially [[RDX]]), [[explosive booster|booster]] and [[burst charge|bursting charges]] of small [[caliber]] [[ammunition]], in upper charges of [[detonator]]s in some [[land mine]]s and shells, as the explosive core of [[detonation cord]].<ref name="urlwww.dynonobel.com">{{cite web|url=http://www.dynonobel.com/files/2010/04/Primacord.pdf |title=Primacord Technical Information |publisher=Dyno Nobel |access-date=April 22, 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110710160725/http://www.dynonobel.com/files/2010/04/Primacord.pdf |archive-date=July 10, 2011 }}</ref><ref>{{Cite journal |title=Explosive power of Pentaerythritol Tetranitrate |date=2020 |pmc=7675531 |last1=Zhang |first1=Y. |last2=Li |first2=Q. |last3=He |first3=Y. |journal=ACS Omega |volume=5 |issue=45 |pages=28984–28991 |doi=10.1021/acsomega.0c03133 |pmid=33225129 }}</ref> PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer than [[nitroglycerin]] or [[nitrocellulose]].<ref>[http://www.britannica.com/EBchecked/topic/454067/PETN PETN (chemical compound)]. ''Encyclopædia Britannica''. Retrieved February 8, 2010.</ref>

During [[World War II]], PETN was most importantly used in [[exploding-bridgewire detonator]]s for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation, compared with [[primacord]]. PETN was used for these detonators because it was safer than primary explosives like [[lead azide]]: while it was sensitive, it would not detonate below a threshold amount of energy.<ref>{{cite book | title = A Technical History of Los Alamos During the Oppenheimer Years, 1943–1945 |author1=Lillian Hoddeson |author2=Paul W. Henriksen |author3=Roger A. Meade |author4=Catherine L. Westfall |author5=Gordon Baym |author6=Richard Hewlett |author7=Alison Kerr |author8=Robert Penneman |author9=Leslie Redman |author10=Robert Seidel | year = 2004 | pages = 164–173 |publisher=Cambridge University Press | url = https://books.google.com/books?id=KoTve97yYB8C&pg=PA164 | format = [[Google Books]] excerpt | isbn = 978-0-521-54117-6}}</ref> Exploding bridgewires containing PETN remain used in current nuclear weapons. In spark detonators, PETN is used to avoid the need for primary explosives; the energy needed for a successful direct initiation of PETN by an [[electric spark]] ranges between 10–60 mJ.

Its basic explosion characteristics are:
* Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1 kg of PETN has the energy of 1.24 kg TNT.
* [[Detonation velocity]]: 8350 m/s (1.73 g/cm3), 7910 m/s (1.62 g/cm3), 7420 m/s (1.5 g/cm3), 8500 m/s (pressed in a steel tube)
* Volume of gases produced: 790 dm3/kg (other value: 768 dm3/kg)
* Explosion temperature: 4230 °C
* [[Oxygen balance]]: −6.31 atom -g/kg
* [[Melting point]]: 141.3 °C (pure), 140–141 °C (technical)
* [[Trauzl lead block test]]: 523 cm3 (other values: 500 cm3 when sealed with sand, or 560 cm3 when sealed with water)
* Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9 mm for PETN at 1 g/cm3, smaller for higher densities (other value: 1.5 mm)

===In mixtures===
PETN is used in a number of compositions. It is a major ingredient of the [[Semtex]] [[plastic explosive]]. It is also used as a component of [[pentolite]], a 50/50 blend with TNT. The XTX8003 extrudable explosive, used in the [[W68]] and [[W76]] nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, a [[silicone rubber]].<ref>{{cite tech report |last1=Shepodd | first1=T | last2=Behrens | first2=R | last3=Anex | first3=D | last4=Miller | first4=D | last5=Anderson | first5=K |date=1997-07-01 |title= Degradation chemistry of PETN and its homologues |institution= Sandia National Laboratory |number= SAND-97-8684C | osti=650196 | url=https://www.osti.gov/servlets/purl/650196 | access-date= May 14, 2023}}</ref> It is often [[phlegmatized]] by addition of 5–40% of [[wax]], or by polymers (producing [[polymer-bonded explosive]]s); in this form it is used in some cannon shells up to [[30 mm caliber]], though it is unsuitable for higher calibers.  It is also used as a component of some gun [[propellant]]s and [[solid rocket propellant]]s. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot be [[casting|cast]] as it explosively decomposes slightly above its melting point,{{citation needed|date=September 2016}}{{clarify|date=September 2016}} but it can be mixed with other explosives to form castable mixtures.

PETN can be initiated by a [[laser]].<ref>{{cite journal | last1 = Tarzhanov | first1 = V. I. | last2 = Zinchenko | first2 = A. D. | last3 = Sdobnov | first3 = V. I. | last4 = Tokarev | first4 = B. B. | last5 = Pogrebov | first5 = A. I. | last6 = Volkova | first6 = A. A. | title = Laser initiation of PETN | journal = Combustion, Explosion, and Shock Waves | volume = 32 | issue = 4 | page = 454 | year = 1996 | doi = 10.1007/BF01998499| s2cid = 98083192 }}</ref> A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a [[Q-switching|Q-switched]] [[ruby laser]] can initiate detonation of a PETN surface coated with a 100 nm thick aluminium layer in less than half of a microsecond.{{Citation needed|date=November 2010}}

PETN has been replaced in many applications by [[RDX]], which is thermally more stable and has a longer [[shelf life]].<ref>US Army – Encyclopedia of Explosives and Related Items, vol.8</ref> PETN can be used in some [[ram accelerator]] types.<ref>[http://fluid.ippt.gov.pl/ictam04/CD_ICTAM04/FM3/12843/FM3_12843.pdf Simulation of ram accelerator with PETN layer], Arkadiusz Kobiera and Piotr Wolanski, XXI ICTAM, August 15–21, 2004, Warsaw, Poland</ref> Replacement of the central carbon atom with [[silicon]] produces Si-PETN, which is extremely sensitive.<ref>{{cite journal|url=http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|title=Explanation of the Colossal Detonation Sensitivity of Silicon Pentaerythritol Tetranitrate (Si-PETN) Explosive|author=Wei-Guang Liu|journal=J. Am. Chem. Soc.|year=2009|volume=131|pages=7490–1|doi=10.1021/ja809725p|pmid=19489634|issue=22|display-authors=etal|access-date=January 3, 2010|archive-date=March 21, 2018|archive-url=https://web.archive.org/web/20180321192503/http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|url-status=dead}}</ref><ref>[http://comporgchem.com/blog/?p=258 Computational Organic Chemistry » Si-PETN sensitivity explained]. Comporgchem.com (July 20, 2009). Retrieved 2010-02-08.</ref>

===Terrorist use===
{{Main|Shoe Bomber|2009 Christmas Day bomb plot|2010 cargo plane bomb plot}}

Ten kilograms of PETN was used in the [[1980 Paris synagogue bombing]].

In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at the [[1983 Beirut barracks bombings|Beirut barracks]].

In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of {{convert|24|kg|lb}} of PETN by terrorist [[Johannes Weinrich]].<ref>{{cite news|url=http://www.spiegel.de/panorama/0,1518,56218,00.html |title=Article detailing attack on Maison de France in Berlin (German) |work=Der Spiegel |date=December 13, 1999 |access-date=November 4, 2010}}</ref>

In 1999, [[Alfred Heinz Reumayr]] used PETN as the main charge for his fourteen [[improvised explosive device]]s that he constructed in a thwarted attempt to damage the [[Trans-Alaska Pipeline System]].

In 2001, [[al-Qaeda]] member [[Richard Reid (shoe bomber)|Richard Reid]], the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow up [[2001 American Airlines Flight 63 bombing attempt|American Airlines Flight 63]] from Paris to Miami.<ref name="latimes.com"/><ref name="urlBBC News|AMERICAS|Shoe bomb suspect did not act alone">{{cite news|url = http://news.bbc.co.uk/2/hi/americas/1783237.stm|title = 'Shoe bomb suspect 'did not act alone'|date = January 25, 2002|work = BBC News|access-date = April 22, 2009}}</ref> He had intended to use the solid [[triacetone triperoxide]] (TATP) as a detonator.<ref name=nyt/>

In 2009, PETN was used in an attempt by [[al-Qaeda in the Arabian Peninsula]] to murder the Saudi Arabian Deputy Minister of Interior Prince [[Muhammad bin Nayef]], by Saudi [[suicide bomber]] [[Abdullah Hassan Al Aseery|Abdullah Hassan al Asiri]]. The target survived and the bomber died in the blast. The PETN was hidden in the bomber's [[rectum]], which security experts described as a novel technique.<ref>{{cite web|url=http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|title=Saudi suicide bomber hid IED in his anal cavity|date=September 9, 2009|work=Homeland Security Newswire|access-date=December 28, 2009|archive-url=https://web.archive.org/web/20091231030044/http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|archive-date=December 31, 2009|url-status=dead}}</ref><ref>{{cite web|url=https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-url=https://ghostarchive.org/archive/20221210/https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-date=December 10, 2022 |url-status=live|author=England, Andrew |title= Bomb clues point to Yemeni terrorists |work=Financial Times |date=November 1, 2010 |url-access=subscription}}</ref><ref>{{cite news |url=https://www.cbsnews.com/news/saudi-bombmaker-key-suspect-in-yemen-plot/ |title=Saudi Bombmaker Key Suspect in Yemen Plot |publisher=CBS News |date=November 1, 2010 |access-date=November 2, 2010 |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102214722/http://www.cbsnews.com/stories/2010/11/01/world/main7010288.shtml |url-status=live }}</ref>

On 25 December 2009, PETN was found in the underwear of [[Umar Farouk Abdulmutallab]], the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.<ref>
{{cite news
| url = http://www.foxnews.com/story/0,2933,581307,00.html
| title = Al Qaeda Claims Responsibility for Attempted Bombing of U.S. Plane
| date = December 28, 2009
| publisher = FOX News Network
| access-date = December 29, 2009}}</ref> According to US law enforcement officials,<ref>{{cite news|url=http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-date=2022-10-09 |url-status=live |title=Criminal Complaint |access-date=November 4, 2010 |work=[[The Huffington Post]]}}</ref> he had attempted to blow up [[Northwest Airlines Flight 253]] while approaching Detroit from Amsterdam.<ref name="urlABC News|AMERICAS|Investigators: Northwest Bomb Plot Planned by Al-Qaeda in Yemen">{{cite web|url = https://abcnews.go.com/Blotter/northwest-bomb-plot-planned-al-qaeda-yemen/story?id=9426085&page=1|title = Investigators: Northwest Bomb Plot Planned by al Qaeda in Yemen|date = December 26, 2009|publisher = ABC News|access-date = December 26, 2009}}</ref> Abdulmutallab had tried, unsuccessfully, to detonate approximately {{convert|80|g}} of PETN sewn into his underwear by adding liquid from a syringe;<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/28/AR2009122800582.html Explosive in Detroit terror case could have blown hole in airplane, sources say] ''The Washington Post''. Retrieved February 8, 2010.</ref> however, only a small fire resulted.<ref name=nyt/>

In the al-Qaeda in the Arabian Peninsula October [[2010 cargo plane bomb plot]], two PETN-filled printer cartridges were found at [[East Midlands Airport]] and in [[Dubai]] on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computer [[Toner cartridge|printer cartridges]] filled with PETN.<ref name="scientificamerican1">{{cite web|last=Greenemeier |first=Larry |url=http://www.scientificamerican.com/article.cfm?id=aircraft-cargo-bomb-security |title=Exposing the Weakest Link: As Airline Passenger Security Tightens, Bombers Target Cargo Holds |work=Scientific American |access-date=November 3, 2010}}</ref><ref name="nytimes4">{{cite news| url=https://www.nytimes.com/2010/11/02/world/02terror.html?src=twrhp | work=The New York Times | first1=Scott | last1=Shane | first2=Robert F. | last2=Worth | title=Early Parcels Sent to U.S. Were Eyed as Dry Run | date=November 1, 2010}}</ref> The bomb found in England contained {{convert|400|g}} of PETN, and the one found in Dubai contained {{convert|300|g}} of PETN.<ref name="nytimes4"/> Hans Michels, professor of [[safety engineering]] at [[University College London]], told a newspaper that {{convert|6|g}} of PETN—"around 50 times less than was used—would be enough to blast a hole in a metal plate twice the thickness of an aircraft's skin".<ref>{{cite news |url=http://indiatoday.intoday.in/site/Story/118746/World/parcel-bombs-could-rip-50-planes-in-half.html |title=Parcel bombs could rip 50 planes in half |work=[[India Today]] |access-date=November 3, 2010}}</ref> In contrast, according to an experiment conducted by a BBC documentary team designed to simulate Abdulmutallab's Christmas Day bombing, using a Boeing 747 plane, even 80 grams of PETN was not sufficient to materially damage the fuselage.<ref>{{cite web |url=http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |title='Underwear Bomber' Could not have Blown Up Plane |publisher=[[Discovery Channel|Discovery]] |date=March 10, 2010 |access-date=November 16, 2010 |archive-date=October 13, 2010 |archive-url=https://web.archive.org/web/20101013011037/http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |url-status=dead }}</ref>

On 12 July 2017, 150 grams of PETN was found in the Assembly of Uttar Pradesh,<ref>{{Cite web|url=https://indianexpress.com/article/what-is/what-is-petn-explsoive-uttar-pradesh-assembly-yogi-adityanath-4750049/|title = What is PETN explosive device found in Uttar Pradesh Assembly?|date = July 15, 2017}}</ref><ref>{{Cite web|url=http://www.firstpost.com/india/highly-explosive-petn-found-in-uttar-pradesh-assembly-yogi-adityanath-chairs-high-level-meet-demands-nia-probe-3812119.html|title = Highly explosive PETN found in Uttar Pradesh Assembly: Yogi Adityanath demands NIA probe|date = July 14, 2017}}</ref> India's most populous state.<ref>{{cite web |title=Population and decadal change by residence : 2011 (PERSONS) |url=http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-date=2022-10-09 |url-status=live |publisher=Office of the Registrar General & Census Commissioner, India |page=2}}</ref><ref>{{cite web |title=Statistical Year Book 2015 |url=https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-url=https://ghostarchive.org/archive/20221009/https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-date=2022-10-09 |url-status=live |website=telangana.gov.in |publisher=Directorate of Economics and Statistics, Government of Telangana |access-date=4 March 2019}}</ref>

===Detection===
In the wake of terrorist PETN bomb plots, an article in ''[[Scientific American]]'' noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.<ref name="scientificamerican1"/> The ''[[Los Angeles Times]]'' noted in November 2010 that PETN's low [[vapor pressure]] makes it difficult for bomb-sniffing dogs to detect.<ref name="latimes.com"/>

Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves<ref>Committee on the Review of Existing and Potential Standoff Explosives Detection Techniques, National Research Council (2004) [http://www.nap.edu/openbook.php?record_id=10998&page=1 Existing and Potential Standoff Explosives Detection Techniques], National Academies Press, Washington, D.C. p. 77.</ref> and terahertz,<ref>{{cite book|doi=10.1117/12.2197442|chapter=Discrimination and identification of RDX/PETN explosives by chemometrics applied to terahertz time-domain spectral imaging|title=Millimetre Wave and Terahertz Sensors and Technology VIII|volume=9651|pages=965109|year=2015|last1=Bou-Sleiman|first1=J.|last2=Perraud|first2=J.-B.|last3=Bousquet|first3=B.|last4=Guillet|first4=J.-P.|last5=Palka|first5=N.|last6=Mounaix|first6=P.|s2cid=137950290|editor1-last=Salmon|editor1-first=Neil A|editor2-last=Jacobs|editor2-first=Eddie L}}</ref> some of which have been implemented in public screening applications, primarily for air travel. PETN is one of the explosive chemicals typically of interest in that area, and it belongs to a family of common [[Nitro compound|nitrate-based explosive chemicals]] which can often be detected by the same tests.

One detection system in use at airports involves analysis of swab samples obtained from passengers and their baggage. Whole-body imaging scanners that use radio-frequency [[electromagnetic wave]]s, low-intensity [[X-rays]], or T-rays of terahertz frequency that can detect objects hidden under clothing are not widely used because of cost, concerns about the resulting traveler delays, and privacy concerns.<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/27/AR2009122702021.html "Equipment to detect explosives is available"]. ''[[The Washington Post]]''. Retrieved February 8, 2010.</ref>

Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.<ref name="spiegel1"/> [[Qatar Airways]] said the PETN bomb "could not be detected by x-ray screening or trained [[sniffer dog]]s".<ref name="autogenerated1">{{cite news|url=https://www.bbc.co.uk/news/11658452 |title=Q&A: Air freight bomb plot |work=[[BBC News]] |date=October 30, 2010 |access-date=November 3, 2010}}</ref> The [[Federal Criminal Police Office (Germany)|Bundeskriminalamt]] received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.<ref name="spiegel1">{{cite news |url=http://www.spiegel.de/international/world/0,1518,726746,00.html |title=Foiled Parcel Plot: World Scrambles to Tighten Air Cargo Security |work=[[Der Spiegel]] |access-date=November 2, 2010}}</ref><ref name="aljazeera1">{{cite web |url=http://english.aljazeera.net/news/middleeast/2010/10/20101031144429122829.html |title=Passenger jets carried Dubai bomb |publisher=[[Al Jazeera Media Network|Al Jazeera]] |date=October 31, 2010}}</ref> New airport security procedures followed in the U.S., largely to protect against PETN.<ref name="latimes.com"/>

==Medical use==
Like [[nitroglycerin]] (glyceryl trinitrate) and other [[nitrate (pharmacology)|nitrate]]s, PETN is also used medically as a [[vasodilator]] in the treatment of [[heart disease|heart conditions]].<ref name = newdrugs/><ref name=ebadi/> These drugs work by releasing the signaling gas [[nitric oxide]] in the body. The heart medicine ''Lentonitrat'' is nearly pure PETN.<ref>{{cite journal|title = The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate.|author = Russek H. I.| journal =American Journal of the Medical Sciences| volume = 252| issue = 1| pages = 9–20|year = 1966| pmid = 4957459|doi = 10.1097/00000441-196607000-00002|s2cid = 30975527}}</ref>

Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using [[gas chromatography-mass spectrometry]].<ref>Baselt, R. (2008) ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA. pp. 1201–1203. {{ISBN|0962652369}}.</ref>

==See also==
* [[Erythritol tetranitrate]]
* [[RE factor]]

==References==
{{Reflist|30em}}

==Further reading==
{{Commons category|Pentaerythritol tetranitrate}}
* {{cite book|author = Cooper, Paul|title = Explosives Engineering|publisher = Wiley-VCH|location = Weinheim|year = 1997|isbn = 978-0-471-18636-6}}

{{Antianginals (nitrates)}}
{{Nitric oxide signaling}}

{{DEFAULTSORT:Pentaerythritol Tetranitrate}}
[[Category:Antianginals]]
[[Category:Explosive chemicals]]
[[Category:German inventions]]
[[Category:Nitrate esters]]

Pentaerythritol tetranitrate

2024-09-18T09:07:58Z

Leiem: /* Properties */ add crystallographic properties

{{Short description|Explosive chemical compound}}
{{redirect|PETN|the wind power station| Taiba N'Diaye Wind Power Station}}
{{pp-extended|small=yes}}
{{Use mdy dates|date=November 2015}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 477001336
| Name =
| ImageFile =
| ImageFile1 = PETN.svg
| ImageAlt1 = Skeletal formula
| ImageFile2 = PETN-from-xtal-2006-3D-balls-B.png
| ImageAlt2 = Ball-and-stick model
| ImageFile3 = Pentaerythritol tetranitrate 05.jpg
| ImageAlt3 = Pentaerythritol tetranitrate after crystalization from acetone
| ImageSize3 = 235px
| PIN = 2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate
| SystematicName =
| OtherNames = [3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
| IUPACName =
| Section1 = {{Chembox Identifiers
| CASNo = 78-11-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 10L39TRG1Z
| PubChem = 6518
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6271
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 466659
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TZRXHJWUDPFEEY-UHFFFAOYSA-N
| SMILES = C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
| InChI = InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
}}
| Section2 = {{Chembox Properties
| C=5 | H=8 | N=4 | O=12
| Appearance = White crystalline solid<ref name=epa1>{{Cite journal|url=https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-url=https://web.archive.org/web/20240801034435/https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf |archive-date=2024-08-01 |url-status=live|title=Provisional Peer-Reviewed Toxicity Values for Pentaerythritol Tetranitrate (PETN) (CASRN 78-11-5)|date=July 2021|publisher=United States Environmental Protection Agency |journal=Provisional Peer-Reviewed Toxicity Values}}</ref>
| MolarMass = 316.137 g/mol
| Density = 1.77 g/cm3 at 20 °C
| MeltingPtC = 141.3
| BoilingPtC = 180
| BoilingPt_notes = (decomposes above {{convert|150|C|F}})
| Solubility =
}}
| Section3 = {{Chembox Explosive
| ShockSens = Medium
| FrictionSens = Medium
| DetonationV = 8400 m/s (density 1.7 g/cm3)
| REFactor = 1.66}}
| Section4 = {{Chembox Hazards
| GHSPictograms = {{GHS06}} {{GHS01}} {{GHS health hazard}}
| GHSSignalWord = '''Danger'''
| HPhrases = {{H-phrases|201|302|316|370|373|241}}
| PPhrases = {{P-phrases|210|250|261|264|301+312|372|401|501|370+380}}
| NFPA-F = 1
| NFPA-H = 2
| NFPA-R = 3
| FlashPt =
| AutoignitionPtC = 190
}}
| Section5 = {{Chembox Pharmacology
| ATCCode_prefix = C01
| ATCCode_suffix = DA05
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| Pregnancy_category =
| Pregnancy_AU =
}}
| Section6 =
}}

'''Pentaerythritol tetranitrate''' ('''PETN'''), also known as '''PENT''', '''pentyl''', '''PENTA''' ('''''ПЕНТА''''', primarily in Russian), '''TEN''' (tetraeritrit nitrate), '''corpent''', or '''penthrite''' (or, rarely and primarily in German, as '''''nitropenta'''''), is an [[explosive]] material. It is the [[nitrate ester]] of [[pentaerythritol]], and is structurally very similar to [[nitroglycerin]]. [[Penta-|Penta]] refers to the five [[carbon atom]]s of the [[neopentane]] skeleton. PETN is a very powerful explosive material with a [[relative effectiveness factor]] of 1.66.<ref name="urlPETN [Pentaerythritol tetranitrate]">{{cite web |url= http://www.globalsecurity.org/military/systems/munitions/explosives-nitrate-petn.htm |title=PETN (Pentaerythritol tetranitrate) |access-date=March 29, 2010}}</ref> When mixed with a [[plasticizer]], PETN forms a [[plastic explosive]].<ref>{{cite encyclopedia |title = Explosives |encyclopedia = A dictionary of military history and the art of war |last= Childs |first= John |url = https://books.google.com/books?id=nEQ7FUAdmc8C&pg=PA231 |format = [[Google Books]] extract |isbn = 978-0-631-16848-5 |year = 1994}}</ref> Along with [[RDX]] it is the main ingredient of [[Semtex]].

PETN is also used as a [[Vasodilation|vasodilator]] drug to treat certain heart conditions, such as for management of [[angina]].<ref name = newdrugs>{{cite journal |pmc = 1831125 |title = New Drugs |journal = [[Can Med Assoc J]] |year = 1959 |volume = 80 |pages = 997–998 |pmid=20325960 |issue=12}}</ref><ref name = ebadi>{{cite book |title = CRC desk reference of clinical pharmacology |page = 383 |author = Ebadi, Manuchair S. |year = 1998 |publisher = CRC Press |isbn = 978-0-8493-9683-0 |url = https://books.google.com/books?id=-EAxShTKfGAC&pg=PA383 |format = [[Google Books]] excerpt}}</ref>

==History==
Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer {{Interlanguage link|RWS (company)|lt=Rheinisch-Westfälische Sprengstoff A.G.|de|RWS (Unternehmen)}} of [[Cologne|Cologne, Germany]].<ref>Deutsches Reichspatent 81,664 (1894)</ref><ref>Thieme, Bruno [http://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541,899.PN.%2526OS%3DPN%2F0541,899%2526RS%3DPN%2F0541,899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page "Process of making nitropentaerythrit,"] {{Webarchive|url=https://web.archive.org/web/20210711151323/https://pdfpiw.uspto.gov/.piw?Docid=00541899&homeurl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526d%3DPALL%2526p%3D1%2526u%3D%25252Fnetahtml%25252FPTO%25252Fsrchnum.htm%2526r%3D1%2526f%3DG%2526l%3D50%2526s1%3D0541%2C899.PN.%2526OS%3DPN%2F0541%2C899%2526RS%3DPN%2F0541%2C899&PageNum=&Rtype=&SectionNum=&idkey=NONE&Input=View+first+page |date=July 11, 2021 }} U.S. patent no. 541,899 (filed: November 13, 1894; issued: July 2, 1895).</ref><ref>Krehl, Peter O. K. (2009) ''History of Shock Waves, Explosions and Impact''. Berlin, Germany: Springer-Verlag. [https://books.google.com/books?id=PmuqCHDC3pwC&pg=PA405 p. 405].</ref><ref>Urbański, Tadeusz; Ornaf, Władysław and Laverton, Sylvia (1965) ''Chemistry and Technology of Explosives'', vol. 2 (Oxford, England: Permagon Press. [https://archive.org/stream/ChemistryAndTechnologyOfExplosives-VolumeIi/ChemistryAndTechnologyOfExplosives-VolumeIi-TadeuszUrbanski#page/n183/mode/2up p. 175.]
</ref> The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military in {{nowrap|[[World War I]]}}.<ref>German Patent 265,025 (1912)</ref><ref>{{cite book|title = Die Schiess- und Sprengstoffe|author = Stettbacher, Alfred |place = Leipzig |publisher= Barth|year = 1933| page= 459| edition = 2. völlig umgearb. Aufl. }}</ref> It was also used in the [[MG FF cannon|MG FF/M autocannons]] and many other weapon systems of the [[Luftwaffe]] in World War II.{{cn|date=September 2024}}

==Properties==
PETN is practically [[solubility|insoluble]] in water (0.01 g/100 mL at 50 °C), weakly soluble in common nonpolar [[solvent]]s such as [[Aliphatic compound|aliphatic hydrocarbon]]s (like gasoline) or [[Carbon tetrachloride|tetrachloromethane]], but soluble in some other organic solvents, particularly in [[acetone]] (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and [[dimethylformamide]] (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). It is a non-planar molecule that crystallizes in the space group ''P''{{overline|4}}21''c''.<ref>{{cite journal|author=Zhurova, Elizabeth A.; Stash, Adam I.; Tsirelson, Vladimir G.; Zhurov, Vladimir V.; Bartashevich, Ekaterina V.; Potemkin, Vladimir A.; Pinkerton, A. Alan|year=2006|title=Atoms-in-Molecules Study of Intra- and Intermolecular Bonding in the Pentaerythritol Tetranitrate Crystal. Journal of the American Chemical Society|volume=128|issue=45|pages=14728–14734|doi=10.1021/ja0658620}}</ref> PETN forms [[eutectic system|eutectic]] mixtures with some liquid or molten [[aromaticity|aromatic]] [[nitro compound]]s, ''e.g.'' [[trinitrotoluene]] (TNT) or [[tetryl]]. Due to steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemical [[reagent]]s; it does not [[hydrolysis|hydrolyze]] in water at room temperature or in weaker [[alkalinity|alkaline]] [[aqueous solution]]s. Water at 100 °C or above causes [[hydrolysis]] to dinitrate; presence of 0.1% [[nitric acid]] accelerates the reaction.

The [[chemical stability]] of PETN is of interest, because of the presence of PETN in aging weapons.<ref>{{Cite tech report | title = Aging of Pentaerythritol Tetranitrate (PETN) | url = https://www.osti.gov/servlets/purl/966904 | last = Foltz | first = M. F. | institution = [[Lawrence Livermore National Laboratory]] | date = July 27, 2009 | number = LLNL-TR-415057 | osti = 966904 | access-date = May 14, 2023 }}</ref> [[Neutron radiation]] degrades PETN, producing [[carbon dioxide]] and some pentaerythritol dinitrate and [[Nitrate|trinitrate]]. [[Gamma radiation]] increases the [[thermal decomposition]] sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary [[Chemical decomposition|degradation]] mechanism is the loss of [[nitrogen dioxide]]; this reaction is [[autocatalytic]].{{Citation needed|date=November 2010}} Studies were performed on [[thermal decomposition]] of PETN.<ref>German, V.N. et al. [http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf Thermal decomposition of PENT and HMX over a wide temperature range] {{Webarchive|url=https://web.archive.org/web/20200410211224/http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/German-258.pdf |date=April 10, 2020 }}. Institute of Physics of Explosion, RFNC-VNIIEF, Sarov, Russia</ref>

In the environment, PETN undergoes [[biodegradation]]. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.<ref>{{Cite journal|last1=Zhuang|first1=Li|last2=Gui|first2=Lai|last3=Gillham|first3=Robert W.|date=2012-10-01|title=Biodegradation of pentaerythritol tetranitrate (PETN) by anaerobic consortia from a contaminated site|url=http://www.sciencedirect.com/science/article/pii/S0045653512005942|journal=Chemosphere|language=en|volume=89|issue=7|pages=810–816|doi=10.1016/j.chemosphere.2012.04.062|pmid=22647196|bibcode=2012Chmsp..89..810Z|issn=0045-6535}}</ref> PETN has low [[Volatility (chemistry)|volatility]] and low solubility in water, and therefore has low [[bioavailability]] for most organisms. Its [[toxicity]] is relatively low, and its [[transdermal]] absorption also seems to be low. It poses a threat for aquatic [[organism]]s. It can be degraded to pentaerythritol by [[iron]].<ref>{{cite journal|doi=10.1021/es7029703|title=Degradation of Pentaerythritol Tetranitrate (PETN) by Granular Iron|journal=[[Environ. Sci. Technol.]]|year=2008|volume=42|pages=4534–9|pmid=18605582|issue=12|last1=Zhuang|first1=L|last2=Gui|first2=L|last3=Gillham|first3=R. W.|bibcode=2008EnST...42.4534Z}}</ref>

==Production==

Production is by the reaction of [[pentaerythritol]] with concentrated [[nitric acid]] to form a precipitate which can be recrystallized from acetone to give processable crystals.<ref name = Ullmann>{{Ullmann | doi = 10.1002/14356007.a10_143.pub2 | title = Explosives | author = Boileau, Jacques | author2 = Fauquignon, Claude | author3 = Hueber, Bernard | author4 = Meyer, Hans H. | name-list-style=amp }}</ref>

Variations of a method first published in US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) form the basis of all current commercial production.{{cn|date=September 2024}}

PETN is manufactured by numerous manufacturers as a powder, or together with [[nitrocellulose]] and [[plasticizer]] as thin plasticized sheets (e.g. [[Primasheet]] 1000 or [[Detasheet]]). PETN residues are easily detectable in hair of people handling it.<ref>Winslow, Ron. (December 29, 2009) [https://www.wsj.com/articles/SB126195987401406861 A Primer in PETN – WSJ.com]. ''The Wall Street Journal''. Retrieved 2010-02-08.</ref> The highest residue retention is on black hair; some residues remain even after washing.<ref>{{cite journal | last1 = Oxley | first1 = Jimmie C. | last2 = Smith | first2 = James L. | last3 = Kirschenbaum | first3 = Louis J. | last4 = Shinde | first4 = Kajal. P. | last5 = Marimganti | first5 = Suvarna | title = Accumulation of Explosives in Hair | journal = Journal of Forensic Sciences | volume = 50 | issue = 4 | year = 2005 | pages = 826–31 | doi = 10.1520/JFS2004545| pmid = 16078483 }}</ref><ref name="latimes.com">{{cite news| url=https://www.latimes.com/archives/la-xpm-2010-nov-24-la-na-petn-20101124-story.html |title= PETN: The explosive that airport security is targeting |last=Bennett |first=Brian |agency=Tribune Washington Bureau |date=November 24, 2010 |work=Los Angeles Times |access-date=July 19, 2015}}</ref>

==Explosive use==

[[File:Pentryt.jpg|thumbnail|Pentaerythritol tetranitrate before crystallization from acetone]]

The most common use of PETN is as an explosive with high [[brisance]]. It is a [[secondary explosive]], meaning it is more difficult to detonate than [[primary explosive]]s, so dropping or igniting it will typically not cause an explosion (at [[standard atmospheric pressure]] it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such as [[TNT]] or [[tetryl]].<ref name = Ullmann/><ref name=nyt>{{Cite news|url=https://www.nytimes.com/2009/12/28/us/28explosives.html?ref=us|title=Explosive on Flight 253 Is Among Most Powerful |newspaper=The New York Times|date=December 27, 2009|author=Chang, Kenneth }}</ref> Under certain conditions a [[deflagration to detonation transition]] can occur, just like that of [[ammonium nitrate]].

It is rarely used alone in military operations due to its lower stability, but primarily used in main charges of plastic explosives such as [[C-4 (explosive)|C4]] along with other explosives (especially [[RDX]]), [[explosive booster|booster]] and [[burst charge|bursting charges]] of small [[caliber]] [[ammunition]], in upper charges of [[detonator]]s in some [[land mine]]s and shells, as the explosive core of [[detonation cord]].<ref name="urlwww.dynonobel.com">{{cite web|url=http://www.dynonobel.com/files/2010/04/Primacord.pdf |title=Primacord Technical Information |publisher=Dyno Nobel |access-date=April 22, 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110710160725/http://www.dynonobel.com/files/2010/04/Primacord.pdf |archive-date=July 10, 2011 }}</ref><ref>{{Cite journal |title=Explosive power of Pentaerythritol Tetranitrate |date=2020 |pmc=7675531 |last1=Zhang |first1=Y. |last2=Li |first2=Q. |last3=He |first3=Y. |journal=ACS Omega |volume=5 |issue=45 |pages=28984–28991 |doi=10.1021/acsomega.0c03133 |pmid=33225129 }}</ref> PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer than [[nitroglycerin]] or [[nitrocellulose]].<ref>[http://www.britannica.com/EBchecked/topic/454067/PETN PETN (chemical compound)]. ''Encyclopædia Britannica''. Retrieved February 8, 2010.</ref>

During [[World War II]], PETN was most importantly used in [[exploding-bridgewire detonator]]s for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation, compared with [[primacord]]. PETN was used for these detonators because it was safer than primary explosives like [[lead azide]]: while it was sensitive, it would not detonate below a threshold amount of energy.<ref>{{cite book | title = A Technical History of Los Alamos During the Oppenheimer Years, 1943–1945 |author1=Lillian Hoddeson |author2=Paul W. Henriksen |author3=Roger A. Meade |author4=Catherine L. Westfall |author5=Gordon Baym |author6=Richard Hewlett |author7=Alison Kerr |author8=Robert Penneman |author9=Leslie Redman |author10=Robert Seidel | year = 2004 | pages = 164–173 |publisher=Cambridge University Press | url = https://books.google.com/books?id=KoTve97yYB8C&pg=PA164 | format = [[Google Books]] excerpt | isbn = 978-0-521-54117-6}}</ref> Exploding bridgewires containing PETN remain used in current nuclear weapons. In spark detonators, PETN is used to avoid the need for primary explosives; the energy needed for a successful direct initiation of PETN by an [[electric spark]] ranges between 10–60 mJ.

Its basic explosion characteristics are:
* Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1 kg of PETN has the energy of 1.24 kg TNT.
* [[Detonation velocity]]: 8350 m/s (1.73 g/cm3), 7910 m/s (1.62 g/cm3), 7420 m/s (1.5 g/cm3), 8500 m/s (pressed in a steel tube)
* Volume of gases produced: 790 dm3/kg (other value: 768 dm3/kg)
* Explosion temperature: 4230 °C
* [[Oxygen balance]]: −6.31 atom -g/kg
* [[Melting point]]: 141.3 °C (pure), 140–141 °C (technical)
* [[Trauzl lead block test]]: 523 cm3 (other values: 500 cm3 when sealed with sand, or 560 cm3 when sealed with water)
* Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9 mm for PETN at 1 g/cm3, smaller for higher densities (other value: 1.5 mm)

===In mixtures===
PETN is used in a number of compositions. It is a major ingredient of the [[Semtex]] [[plastic explosive]]. It is also used as a component of [[pentolite]], a 50/50 blend with TNT. The XTX8003 extrudable explosive, used in the [[W68]] and [[W76]] nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, a [[silicone rubber]].<ref>{{cite tech report |last1=Shepodd | first1=T | last2=Behrens | first2=R | last3=Anex | first3=D | last4=Miller | first4=D | last5=Anderson | first5=K |date=1997-07-01 |title= Degradation chemistry of PETN and its homologues |institution= Sandia National Laboratory |number= SAND-97-8684C | osti=650196 | url=https://www.osti.gov/servlets/purl/650196 | access-date= May 14, 2023}}</ref> It is often [[phlegmatized]] by addition of 5–40% of [[wax]], or by polymers (producing [[polymer-bonded explosive]]s); in this form it is used in some cannon shells up to [[30 mm caliber]], though it is unsuitable for higher calibers.  It is also used as a component of some gun [[propellant]]s and [[solid rocket propellant]]s. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot be [[casting|cast]] as it explosively decomposes slightly above its melting point,{{citation needed|date=September 2016}}{{clarify|date=September 2016}} but it can be mixed with other explosives to form castable mixtures.

PETN can be initiated by a [[laser]].<ref>{{cite journal | last1 = Tarzhanov | first1 = V. I. | last2 = Zinchenko | first2 = A. D. | last3 = Sdobnov | first3 = V. I. | last4 = Tokarev | first4 = B. B. | last5 = Pogrebov | first5 = A. I. | last6 = Volkova | first6 = A. A. | title = Laser initiation of PETN | journal = Combustion, Explosion, and Shock Waves | volume = 32 | issue = 4 | page = 454 | year = 1996 | doi = 10.1007/BF01998499| s2cid = 98083192 }}</ref> A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a [[Q-switching|Q-switched]] [[ruby laser]] can initiate detonation of a PETN surface coated with a 100 nm thick aluminium layer in less than half of a microsecond.{{Citation needed|date=November 2010}}

PETN has been replaced in many applications by [[RDX]], which is thermally more stable and has a longer [[shelf life]].<ref>US Army – Encyclopedia of Explosives and Related Items, vol.8</ref> PETN can be used in some [[ram accelerator]] types.<ref>[http://fluid.ippt.gov.pl/ictam04/CD_ICTAM04/FM3/12843/FM3_12843.pdf Simulation of ram accelerator with PETN layer], Arkadiusz Kobiera and Piotr Wolanski, XXI ICTAM, August 15–21, 2004, Warsaw, Poland</ref> Replacement of the central carbon atom with [[silicon]] produces Si-PETN, which is extremely sensitive.<ref>{{cite journal|url=http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|title=Explanation of the Colossal Detonation Sensitivity of Silicon Pentaerythritol Tetranitrate (Si-PETN) Explosive|author=Wei-Guang Liu|journal=J. Am. Chem. Soc.|year=2009|volume=131|pages=7490–1|doi=10.1021/ja809725p|pmid=19489634|issue=22|display-authors=etal|access-date=January 3, 2010|archive-date=March 21, 2018|archive-url=https://web.archive.org/web/20180321192503/http://www.wag.caltech.edu/publications/sup/pdf/806.pdf|url-status=dead}}</ref><ref>[http://comporgchem.com/blog/?p=258 Computational Organic Chemistry » Si-PETN sensitivity explained]. Comporgchem.com (July 20, 2009). Retrieved 2010-02-08.</ref>

===Terrorist use===
{{Main|Shoe Bomber|2009 Christmas Day bomb plot|2010 cargo plane bomb plot}}

Ten kilograms of PETN was used in the [[1980 Paris synagogue bombing]].

In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at the [[1983 Beirut barracks bombings|Beirut barracks]].

In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of {{convert|24|kg|lb}} of PETN by terrorist [[Johannes Weinrich]].<ref>{{cite news|url=http://www.spiegel.de/panorama/0,1518,56218,00.html |title=Article detailing attack on Maison de France in Berlin (German) |work=Der Spiegel |date=December 13, 1999 |access-date=November 4, 2010}}</ref>

In 1999, [[Alfred Heinz Reumayr]] used PETN as the main charge for his fourteen [[improvised explosive device]]s that he constructed in a thwarted attempt to damage the [[Trans-Alaska Pipeline System]].

In 2001, [[al-Qaeda]] member [[Richard Reid (shoe bomber)|Richard Reid]], the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow up [[2001 American Airlines Flight 63 bombing attempt|American Airlines Flight 63]] from Paris to Miami.<ref name="latimes.com"/><ref name="urlBBC News|AMERICAS|Shoe bomb suspect did not act alone">{{cite news|url = http://news.bbc.co.uk/2/hi/americas/1783237.stm|title = 'Shoe bomb suspect 'did not act alone'|date = January 25, 2002|work = BBC News|access-date = April 22, 2009}}</ref> He had intended to use the solid [[triacetone triperoxide]] (TATP) as a detonator.<ref name=nyt/>

In 2009, PETN was used in an attempt by [[al-Qaeda in the Arabian Peninsula]] to murder the Saudi Arabian Deputy Minister of Interior Prince [[Muhammad bin Nayef]], by Saudi [[suicide bomber]] [[Abdullah Hassan Al Aseery|Abdullah Hassan al Asiri]]. The target survived and the bomber died in the blast. The PETN was hidden in the bomber's [[rectum]], which security experts described as a novel technique.<ref>{{cite web|url=http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|title=Saudi suicide bomber hid IED in his anal cavity|date=September 9, 2009|work=Homeland Security Newswire|access-date=December 28, 2009|archive-url=https://web.archive.org/web/20091231030044/http://homelandsecuritynewswire.com/saudi-suicide-bomber-hid-ied-his-anal-cavity|archive-date=December 31, 2009|url-status=dead}}</ref><ref>{{cite web|url=https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-url=https://ghostarchive.org/archive/20221210/https://www.ft.com/content/c2a28a88-e606-11df-9cdd-00144feabdc0 |archive-date=December 10, 2022 |url-status=live|author=England, Andrew |title= Bomb clues point to Yemeni terrorists |work=Financial Times |date=November 1, 2010 |url-access=subscription}}</ref><ref>{{cite news |url=https://www.cbsnews.com/news/saudi-bombmaker-key-suspect-in-yemen-plot/ |title=Saudi Bombmaker Key Suspect in Yemen Plot |publisher=CBS News |date=November 1, 2010 |access-date=November 2, 2010 |archive-date=November 2, 2012 |archive-url=https://web.archive.org/web/20121102214722/http://www.cbsnews.com/stories/2010/11/01/world/main7010288.shtml |url-status=live }}</ref>

On 25 December 2009, PETN was found in the underwear of [[Umar Farouk Abdulmutallab]], the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.<ref>
{{cite news
| url = http://www.foxnews.com/story/0,2933,581307,00.html
| title = Al Qaeda Claims Responsibility for Attempted Bombing of U.S. Plane
| date = December 28, 2009
| publisher = FOX News Network
| access-date = December 29, 2009}}</ref> According to US law enforcement officials,<ref>{{cite news|url=http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://big.assets.huffingtonpost.com/AbdumutallabCharges.pdf |archive-date=2022-10-09 |url-status=live |title=Criminal Complaint |access-date=November 4, 2010 |work=[[The Huffington Post]]}}</ref> he had attempted to blow up [[Northwest Airlines Flight 253]] while approaching Detroit from Amsterdam.<ref name="urlABC News|AMERICAS|Investigators: Northwest Bomb Plot Planned by Al-Qaeda in Yemen">{{cite web|url = https://abcnews.go.com/Blotter/northwest-bomb-plot-planned-al-qaeda-yemen/story?id=9426085&page=1|title = Investigators: Northwest Bomb Plot Planned by al Qaeda in Yemen|date = December 26, 2009|publisher = ABC News|access-date = December 26, 2009}}</ref> Abdulmutallab had tried, unsuccessfully, to detonate approximately {{convert|80|g}} of PETN sewn into his underwear by adding liquid from a syringe;<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/28/AR2009122800582.html Explosive in Detroit terror case could have blown hole in airplane, sources say] ''The Washington Post''. Retrieved February 8, 2010.</ref> however, only a small fire resulted.<ref name=nyt/>

In the al-Qaeda in the Arabian Peninsula October [[2010 cargo plane bomb plot]], two PETN-filled printer cartridges were found at [[East Midlands Airport]] and in [[Dubai]] on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computer [[Toner cartridge|printer cartridges]] filled with PETN.<ref name="scientificamerican1">{{cite web|last=Greenemeier |first=Larry |url=http://www.scientificamerican.com/article.cfm?id=aircraft-cargo-bomb-security |title=Exposing the Weakest Link: As Airline Passenger Security Tightens, Bombers Target Cargo Holds |work=Scientific American |access-date=November 3, 2010}}</ref><ref name="nytimes4">{{cite news| url=https://www.nytimes.com/2010/11/02/world/02terror.html?src=twrhp | work=The New York Times | first1=Scott | last1=Shane | first2=Robert F. | last2=Worth | title=Early Parcels Sent to U.S. Were Eyed as Dry Run | date=November 1, 2010}}</ref> The bomb found in England contained {{convert|400|g}} of PETN, and the one found in Dubai contained {{convert|300|g}} of PETN.<ref name="nytimes4"/> Hans Michels, professor of [[safety engineering]] at [[University College London]], told a newspaper that {{convert|6|g}} of PETN—"around 50 times less than was used—would be enough to blast a hole in a metal plate twice the thickness of an aircraft's skin".<ref>{{cite news |url=http://indiatoday.intoday.in/site/Story/118746/World/parcel-bombs-could-rip-50-planes-in-half.html |title=Parcel bombs could rip 50 planes in half |work=[[India Today]] |access-date=November 3, 2010}}</ref> In contrast, according to an experiment conducted by a BBC documentary team designed to simulate Abdulmutallab's Christmas Day bombing, using a Boeing 747 plane, even 80 grams of PETN was not sufficient to materially damage the fuselage.<ref>{{cite web |url=http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |title='Underwear Bomber' Could not have Blown Up Plane |publisher=[[Discovery Channel|Discovery]] |date=March 10, 2010 |access-date=November 16, 2010 |archive-date=October 13, 2010 |archive-url=https://web.archive.org/web/20101013011037/http://news.discovery.com/tech/underwear-bomber-explosion-plane-test.html |url-status=dead }}</ref>

On 12 July 2017, 150 grams of PETN was found in the Assembly of Uttar Pradesh,<ref>{{Cite web|url=https://indianexpress.com/article/what-is/what-is-petn-explsoive-uttar-pradesh-assembly-yogi-adityanath-4750049/|title = What is PETN explosive device found in Uttar Pradesh Assembly?|date = July 15, 2017}}</ref><ref>{{Cite web|url=http://www.firstpost.com/india/highly-explosive-petn-found-in-uttar-pradesh-assembly-yogi-adityanath-chairs-high-level-meet-demands-nia-probe-3812119.html|title = Highly explosive PETN found in Uttar Pradesh Assembly: Yogi Adityanath demands NIA probe|date = July 14, 2017}}</ref> India's most populous state.<ref>{{cite web |title=Population and decadal change by residence : 2011 (PERSONS) |url=http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-url=https://ghostarchive.org/archive/20221009/http://www.censusindia.gov.in/2011census/PCA/PCA_Highlights/pca_highlights_file/India/Chapter-1.pdf |archive-date=2022-10-09 |url-status=live |publisher=Office of the Registrar General & Census Commissioner, India |page=2}}</ref><ref>{{cite web |title=Statistical Year Book 2015 |url=https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-url=https://ghostarchive.org/archive/20221009/https://www.telangana.gov.in/PDFDocuments/Statistical%20Year%20Book%202015.pdf |archive-date=2022-10-09 |url-status=live |website=telangana.gov.in |publisher=Directorate of Economics and Statistics, Government of Telangana |access-date=4 March 2019}}</ref>

===Detection===
In the wake of terrorist PETN bomb plots, an article in ''[[Scientific American]]'' noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.<ref name="scientificamerican1"/> The ''[[Los Angeles Times]]'' noted in November 2010 that PETN's low [[vapor pressure]] makes it difficult for bomb-sniffing dogs to detect.<ref name="latimes.com"/>

Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves<ref>Committee on the Review of Existing and Potential Standoff Explosives Detection Techniques, National Research Council (2004) [http://www.nap.edu/openbook.php?record_id=10998&page=1 Existing and Potential Standoff Explosives Detection Techniques], National Academies Press, Washington, D.C. p. 77.</ref> and terahertz,<ref>{{cite book|doi=10.1117/12.2197442|chapter=Discrimination and identification of RDX/PETN explosives by chemometrics applied to terahertz time-domain spectral imaging|title=Millimetre Wave and Terahertz Sensors and Technology VIII|volume=9651|pages=965109|year=2015|last1=Bou-Sleiman|first1=J.|last2=Perraud|first2=J.-B.|last3=Bousquet|first3=B.|last4=Guillet|first4=J.-P.|last5=Palka|first5=N.|last6=Mounaix|first6=P.|s2cid=137950290|editor1-last=Salmon|editor1-first=Neil A|editor2-last=Jacobs|editor2-first=Eddie L}}</ref> some of which have been implemented in public screening applications, primarily for air travel. PETN is one of the explosive chemicals typically of interest in that area, and it belongs to a family of common [[Nitro compound|nitrate-based explosive chemicals]] which can often be detected by the same tests.

One detection system in use at airports involves analysis of swab samples obtained from passengers and their baggage. Whole-body imaging scanners that use radio-frequency [[electromagnetic wave]]s, low-intensity [[X-rays]], or T-rays of terahertz frequency that can detect objects hidden under clothing are not widely used because of cost, concerns about the resulting traveler delays, and privacy concerns.<ref>[https://www.washingtonpost.com/wp-dyn/content/article/2009/12/27/AR2009122702021.html "Equipment to detect explosives is available"]. ''[[The Washington Post]]''. Retrieved February 8, 2010.</ref>

Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.<ref name="spiegel1"/> [[Qatar Airways]] said the PETN bomb "could not be detected by x-ray screening or trained [[sniffer dog]]s".<ref name="autogenerated1">{{cite news|url=https://www.bbc.co.uk/news/11658452 |title=Q&A: Air freight bomb plot |work=[[BBC News]] |date=October 30, 2010 |access-date=November 3, 2010}}</ref> The [[Federal Criminal Police Office (Germany)|Bundeskriminalamt]] received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.<ref name="spiegel1">{{cite news |url=http://www.spiegel.de/international/world/0,1518,726746,00.html |title=Foiled Parcel Plot: World Scrambles to Tighten Air Cargo Security |work=[[Der Spiegel]] |access-date=November 2, 2010}}</ref><ref name="aljazeera1">{{cite web |url=http://english.aljazeera.net/news/middleeast/2010/10/20101031144429122829.html |title=Passenger jets carried Dubai bomb |publisher=[[Al Jazeera Media Network|Al Jazeera]] |date=October 31, 2010}}</ref> New airport security procedures followed in the U.S., largely to protect against PETN.<ref name="latimes.com"/>

==Medical use==
Like [[nitroglycerin]] (glyceryl trinitrate) and other [[nitrate (pharmacology)|nitrate]]s, PETN is also used medically as a [[vasodilator]] in the treatment of [[heart disease|heart conditions]].<ref name = newdrugs/><ref name=ebadi/> These drugs work by releasing the signaling gas [[nitric oxide]] in the body. The heart medicine ''Lentonitrat'' is nearly pure PETN.<ref>{{cite journal|title = The therapeutic role of coronary vasodilators: glyceryl trinitrate, isosorbide dinitrate, and pentaerythritol tetranitrate.|author = Russek H. I.| journal =American Journal of the Medical Sciences| volume = 252| issue = 1| pages = 9–20|year = 1966| pmid = 4957459|doi = 10.1097/00000441-196607000-00002|s2cid = 30975527}}</ref>

Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using [[gas chromatography-mass spectrometry]].<ref>Baselt, R. (2008) ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA. pp. 1201–1203. {{ISBN|0962652369}}.</ref>

==See also==
* [[Erythritol tetranitrate]]
* [[RE factor]]

==References==
{{Reflist|30em}}

==Further reading==
{{Commons category|Pentaerythritol tetranitrate}}
* {{cite book|author = Cooper, Paul|title = Explosives Engineering|publisher = Wiley-VCH|location = Weinheim|year = 1997|isbn = 978-0-471-18636-6}}

{{Antianginals (nitrates)}}
{{Nitric oxide signaling}}

{{DEFAULTSORT:Pentaerythritol Tetranitrate}}
[[Category:Antianginals]]
[[Category:Explosive chemicals]]
[[Category:German inventions]]
[[Category:Nitrate esters]]

2,6-Dichloro-4-nitroaniline

2024-09-13T07:53:39Z

Leiem: CAS No. checked

{{Chembox
| ImageFile = Dichloran.svg
| ImageSize = 110
| ImageAlt =
| IUPACName =
| OtherNames = Amino-2,6-dichloro-4-nitrobenzene
|Section1={{Chembox Identifiers
| CASNo = 99-30-9
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment =
| CASNo1 =
| CASNo1_Comment =
| PubChem =
| SMILES = }}
|Section2={{Chembox Properties
| C = 6|H=4|N=2|O=2|Cl=2
| MolarMass =
| Appearance = yellow solid<ref>{{cite journal |doi=10.1039/J19710002181 |title=Crystal structure of 2,6-dichloro-4-nitroaniline |date=1971 |last1=Hughes |first1=David L. |last2=Trotter |first2=James |journal=Journal of the Chemical Society A: Inorganic, Physical, Theoretical |page=2181 }}</ref>
| Density = 1.624 g/Cm3
| MeltingPtC = 191
| MeltingPt_notes =
| BoilingPtC = 130
| BoilingPt_notes = 2 torr
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''2,6-Dichloro-4-nitroaniline''' is an [[organic compound]] with the formula {{chem2|O2NC6H2Cl2NH2}}. It is the most widely discussed isomer of dichloronitroaniline. It is mainly used as a precursor to [[azo dye]]s.<ref>{{cite book |doi=10.1002/14356007.o03_o08 |chapter=Azo Dyes, 4. Cationic Dyes |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Raue |first1=Roderich |last2=Kunde |first2=Klaus |last3=Engel |first3=Aloys |isbn=978-3-527-30385-4 }}</ref>
==References==
{{Reflist}}

[[Category:Anilines]]

3,4-Dichloroaniline

2024-09-12T09:31:44Z

Leiem:

{{Chembox
| ImageFile = 3,4-Dichloranilin.svg
| ImageSize = 110
| ImageAlt =
| IUPACName =
| OtherNames = 1-amino-3,4-dichlorobenzene
|Section1={{Chembox Identifiers
| CASNo = 95-76-1
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 16767
| ChEMBL = 1319813
| ChemSpiderID = 13860720
| EC_number = 202-448-4
| Gmelin = 602350
| KEGG = C02791
| PubChem = 7257
| UNII = 20KR9WJ4NS
| UNNumber = 3442 1590
| StdInChI=1S/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2
| StdInChIKey = SDYWXFYBZPNOFX-UHFFFAOYSA-N
2.1.4 SMILES
C1=CC(=C(C=C1N)Cl)Cl
}}
|Section2={{Chembox Properties
| Cl=2|C=6|H=5|N=1
| Appearance =
| Density = 1.57
| LogP = 2.69
| MeltingPtC = 66-71
| MeltingPt_notes =
| BoilingPtC = 272
| BoilingPt_notes =
| Solubility = 92 mg/l at 20 °C
}}
|Section3={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=3,4-Dichloroaniline |url=https://pubchem.ncbi.nlm.nih.gov/compound/7257#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|311|317|318|331|410}}
| PPhrases = {{P-phrases|261|262|264|264+265|270|271|272|273|280|301+316|302+352|304+340|305+354+338|316|317|321|330|333+317|361+364|362+364|391|403+233|405|501}}
| MainHazards =
| NFPA-H = 3
| NFPA-I = 0
| NFPA-F = 1
| FlashPtC = 166
| AutoignitionPtC = 269
}}
}}

'''3,4-Dichloroaniline''' is an [[organic compound]] with the formula C6H3Cl2(NH2). It is one of several isomers of [[dichloroaniline]]. It is a white solid although commercial samples often appear gray. It is a precursor to dyes, agricultural chemicals, and drugs including the [[antimalarial]] [[chlorproguanil]] and the herbicides [[propanil]], [[linuron]], [[DCMU]], and [[diuron]].

==Preparation==
It is produced by [[hydrogenation]] of [[1,2-Dichloro-4-nitrobenzene|3,4-dichloronitrobenzene]].<ref name=Ullmann>{{cite encyclopedia|author1=P. F. Vogt |author2=J. J. Gerulis|title=Amines, Aromatic|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_037|isbn=9783527303854 }}</ref>

==Safety and environmental aspects==
Being a precursor to some herbicides, the toxicity and fate of dichloroaniline is of interest. One pathway for the biodegradation of dichloroaniline is oxidation to the [[catechol]] derivatives.<ref>{{cite journal |doi=10.1016/0045-6535(90)90054-w |title=A review of the fate and toxicity of 3,4-dichloroaniline in aquatic environments |date=1990 |last1=Crossland |first1=N.O. |journal=Chemosphere |volume=21 |issue=12 |pages=1489–1497 |bibcode=1990Chmsp..21.1489C }}</ref>

==References==
{{Reflist}}

{{DEFAULTSORT:Dichloroaniline, 3,4-}}
[[Category:Anilines]]

2,3-Dichloroaniline

2024-09-12T02:32:20Z

Leiem: typo

{{Chembox
| ImageFile = 2,3-Dichloranilin.svg
| ImageSize =
| ImageAlt =
| IUPACName =
| OtherNames = 1-amino-2,3-dichlorobenzene
|Section1={{Chembox Identifiers
| CASNo = 608-27-5
| CASNo_Comment =
| CASNo1 =
| CASNo1_Comment =
| PubChem =
| SMILES = }}
|Section2={{Chembox Properties
| Cl=2|C=6|H=5|N=1
| MolarMass =
| Appearance = colorless oil
| Density = 1.383 g/cm3
| MeltingPtC = 24
| MeltingPt_notes =
| BoilingPtC = 252
| BoilingPt_notes =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}

'''2,3-Dichloroaniline''' is an [[organic compound]] with the formula C6H3Cl2(NH2). It is one of several isomers of [[dichloroaniline]]. It is a colorless oil although commercial samples often appear colored. It is produced by [[hydrogenation]] of [[1,2-Dichloro-3-nitrobenzene|2,3-dichloronitrobenzene]].<ref name=Ullmann>{{cite encyclopedia|author1=P. F. Vogt |author2=J. J. Gerulis|title=Amines, Aromatic|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_037|isbn=9783527303854 }}</ref>

==Safety and environmental aspects==
Its 72-h [[EC50]] is 6.75 mg/L.<ref>{{cite journal |doi= 10.1016/j.chemosphere.2011.05.023|title= Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs|date= 2011|last1= Aruoja|first1= Villem|last2= Sihtmäe|first2= Mariliis|last3= Dubourguier|first3= Henri-Charles|last4= Kahru|first4= Anne|journal= Chemosphere|volume= 84|issue= 10|pages= 1310–1320|pmid= 21664645|bibcode= 2011Chmsp..84.1310A}}</ref> Biodegradation of 2,3-dichloroaniline proceeds via initial ring hydroxylation.<ref>{{cite journal |doi=10.1021/acs.est.4c02173 |title=Compound-Specific Carbon, Nitrogen, and Hydrogen Isotope Analysis to Characterize Aerobic Biodegradation of 2,3-Dichloroaniline by a Mixed Enrichment Culture |date=2024 |last1=Suchana |first1=Shamsunnahar |last2=Araujo |first2=Sofia Pimentel |last3=Lomheim |first3=Line |last4=Mack |first4=E. Erin |last5=Spain |first5=Jim C. |last6=Edwards |first6=Elizabeth |last7=Passeport |first7=Elodie |journal=Environmental Science & Technology |volume=58 |issue=27 |pages=12042–12050 |pmid=38934904 |bibcode=2024EnST...5812042S }}</ref>

==References==
{{Reflist}}

{{DEFAULTSORT:Dichloroaniline, 3,4-}}
[[Category:Anilines]]

Pacific Blue (dye)

2024-09-07T02:01:44Z

Leiem: CAS RN

{{Chembox
| Name = Pacific Blue
| ImageFile = Pacific blue.svg
| ImageSize = 200px
| PIN = 6,8-Difluoro-7-hydroxy-2-oxo-2''H''-1-benzopyran-3-carboxylic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 215868-31-8
| CASNo_Ref = {{Cascite|correct|CAS}}
| Beilstein =
| ChEBI_Ref =
| ChEMBL = 104101
| ChEBI = 63236
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 13906206
| PubChem = 18942321
| InChI = 1S/C10H4F2O5/c11-5-2-3-1-4(9(14)15)10(16)17-8(3)6(12)7(5)13/h1-2,13H,(H,14,15)
| InChIKey = VYNDHICBIRRPFP-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DLBFLQKQABVKGT-UHFFFAOYSA-L
| SMILES = OC(=O)c1cc2cc(F)c(O)c(F)c2oc1=O
}}
| Section2 = {{Chembox Properties
| C=10|H=4|F=2|O=5
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 410367079
}}

'''Pacific Blue''', or systematically 3-carboxy-6,8-difluoro-7-hydroxycoumarin, is a [[fluorophore]] used in [[cell biology]].<ref>{{Cite journal |last=Lee |first=Wei-Chuan |date=1998 |title=Synthesis of Novel Fluorinated Coumarins: Excellent UV-Light Excitable Fluorescent Dyes |journal=Bioorganic & Medicinal Chemistry Letters |volume=8 |issue=1 |pages=3107–3110 |doi=10.1016/s0960-894x(98)00578-2 |pmid=9873685 }}</ref>
Its [[Excitation spectrum|excitation]] maximum lies at 401 nm, while its [[Emission spectrum|emission]] maximum is at 452 nm.<ref>{{Cite web |url=http://www.bdbiosciences.com/us/applications/s/spectrumguidepage |publisher=BD Biosciences |title=Absorption and Emission Spectra — Pacific Blue™ }}</ref> In contrast to the less acidic 7-hydroxy-3-carboxycoumarin (pKa=7.0), the high acidity of the phenol of Pacific Blue (pKa=3.7) causes its fluorescence to remain very high at neutral pH.

Pacific Blue is a member of the group of Pacific dyes, which includes Pacific Orange, Pacific Green, and Pacific Blue. These fluorescent dyes all have an absorption maximum between 400 and 410 nm, but with different emission spectra: this allows simultaneous excitation with one laser, producing emission at maxima of 551nm, 500 nm and 455 nm, respectively<ref name=":02">{{Cite web |url=http://www.thermofisher.com/cz/en/home/life-science/cell-analysis/fluorophores/pacific-blue-dye.html# |title=Pacific Blue dye |publisher=ThermoFisher Scientific }}</ref> (note: absorption and emission maxima may vary depending on the manufacturer).

In flow cytometry Pacific Blue (as well as other Pacific dyes) absorbs near 405 nm, disallowing simultaneous use with other fluorophores which share similar excitation and/or emission spectra, such as Brilliant Violet 421 (BV421) or V450.<ref>{{Cite web |url=https://www.bdbiosciences.com/en-ca/products/reagents/flow-cytometry-reagents/research-reagents/single-color-antibodies-ruo/violet-proliferation-dye-450.562158 |publisher=BD Biosciences |title=Violet Proliferation Dye 450}}</ref>

== Usage ==
For purposes of [[immunohistochemistry]] or targeted staining in general, reactive forms of Pacific Blue are used to label targeting [[Antibody|antibodies]]. Derivatives of Pacific Blue have been used to study small molecule-protein interactions using fluorescence resonance energy transfer (FRET).<ref>{{Cite journal |last=Lee |first=Molly M. |date=2016 |title=Quantification of Small Molecule–Protein Interactions using FRET between Tryptophan and the Pacific Blue Fluorophore |journal=ACS Omega |volume=6 |issue=1 |pages=1266–1276 |doi=10.1021/acsomega.6b00356 |pmid=28058293 |pmc=5204206 }}</ref> Pacific Blue has also been used to study interactions of the anticancer drug paclitaxel (Taxol) with tubulin in living cells.<ref>{{Cite journal |last=Lee |first=Molly M. |date=2017 |title=Synthesis of a Fluorescent Analogue of Paclitaxel that Selectively Binds Microtubules and Sensitively Detects Efflux by P-Glycoprotein |journal=Angewandte Chemie International Edition |volume=56 |issue=1 |pages=6927–6931 |doi=10.1002/anie.201703298 |pmid=28485901 |pmc=5679005 }}</ref> Reactive forms in use include Pacific Blue succinimidyl [[ester]] and Pacific Blue C5-[[Maleimide]].<ref name=":02" />

== References ==

{{reflist}}

[[Category:Staining dyes]]
[[Category:Fluorone dyes]]
[[Category:Coumarins]]

Malonic acid

2024-09-06T02:27:17Z

Leiem: /* Preparation of carbon suboxide */ remove one excess "["

{{Distinguish|malic acid|maleic acid}}
{{short description|Carboxylic acid with chemical formula CH2(COOH)2 }}
{{Chembox
| ImageFile = Malonsäure.svg
| ImageAlt = Skeletal formula of malonic acid
| ImageFile1 = Malonic acid molecule ball from xtal.png
| ImageAlt1 = Ball-and-stick model of the malonic acid molecule
| PIN = Propanedioic acid<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=746 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = Methanedicarboxylic acid
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 141-82-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9KX7ZMG0MK
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30794
| PubChem = 867
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 7942
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02175
| SMILES = O=C(O)CC(O)=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 844
| SMILES2 = C(C(=O)O)C(=O)O
| InChI = 1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
| InChIKey = OFOBLEOULBTSOW-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OFOBLEOULBTSOW-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=3 | H=4 | O=4
| MeltingPtC = 135 to 137
| MeltingPt_notes = (decomposes)
| Density = 1.619 g/cm3
| Solubility = 763 g/L
| BoilingPt = decomposes
| pKa = pKa1 = 2.83<ref name="Williams">[http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf pKa Data Compiled by R. Williams (pdf; 77 kB)] {{webarchive|url=https://web.archive.org/web/20100602043012/http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf |date=2010-06-02 }}</ref> pKa2 = 5.69<ref name="Williams" />
| MagSus = -46.3·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| ExternalSDS = [https://beta-static.fishersci.com/content/dam/fishersci/en_US/documents/programs/education/regulatory-documents/sds/chemicals/chemicals-m/S25416.pdf External MSDS]
}}
|Section4={{Chembox Related
| OtherAnions = [[Malonate]]
| OtherFunction_label = [[carboxylic acid]]s
| OtherFunction = [[Oxalic acid]] [[Propionic acid]] [[Succinic acid]] [[Fumaric acid]]
| OtherCompounds = [[Malondialdehyde]] [[Dimethyl malonate]]
}}
}}

'''Malonic acid''' is a [[dicarboxylic acid]] with structure CH2(COOH)2. The [[ion]]ized form of malonic acid, as well as its [[ester]]s and [[salt (chemistry)|salt]]s, are known as '''malonates'''. For example, [[diethyl malonate]] is malonic acid's [[Ethyl group|diethyl]] [[ester]]. The name originates from the [[Greek language|Greek]] word μᾶλον (''malon'') meaning 'apple'.

==History==
Malonic acid<ref name=EB1911>{{cite EB1911 |wstitle=Malonic Acid|volume=17 |page=495}}</ref> is a naturally occurring substance found in many fruits and vegetables.<ref name="gsc">{{cite web |url=http://www.thegoodscentscompany.com/data/rw1030881.html |title=Propanedioic acid |website=The Good Scents Company |access-date=2020-10-07 }}</ref> There is a suggestion that [[citrus]] fruits produced in [[organic farming]] contain higher levels of malonic acid than fruits produced in conventional agriculture.<ref>{{Cite journal| vauthors = Ha CN, Ngoc ND, Ngoc CP, Trung DD, Quang BN |date=2012|url=https://www.researchgate.net/publication/216429503|journal=Acta Horticulturae|volume=933|issue=933|pages=601–606|doi=10.17660/actahortic.2012.933.78|issn=0567-7572|hdl=10400.1/2790|title=Organic Acids Concentration in Citrus Juice from Conventional Versus Organic Farming|hdl-access=free}}</ref>

Malonic acid was first prepared in 1858 by the French chemist [[Victor Dessaignes]] via the oxidation of [[malic acid]].<ref name=EB1911/><ref>{{cite journal| vauthors = Dessaignes V |year=1858| url= http://gallica.bnf.fr/ark:/12148/bpt6k3004t/f76.image.langEN |title=Note sur un acide obtenu par l'oxydation de l'acide malique"] (Note on an acid obtained by oxidation of malic acid)| journal=Comptes rendus| volume=47|pages= 76–79}}</ref>

==Structure and preparation==
The structure has been determined by X-ray [[crystallography]]<ref>{{cite journal |doi=10.1016/S0022-2860(99)00293-8 |title=An experimental charge density study of aliphatic dicarboxylic acids |year=2000 | vauthors = Gopalan RS, Kumaradhas P, Kulkarni GU, Rao CN |journal=Journal of Molecular Structure |volume=521 |issue=1–3 |pages=97–106 |bibcode=2000JMoSt.521...97S }}</ref> and extensive property data including for condensed phase thermochemistry are available from the [[National Institute of Standards and Technology]].<ref>{{cite web|url=https://webbook.nist.gov/cgi/inchi/InChI%3D1S/C3H4O4/c4-2(5)1-3(6)7/h1H2%2C(H%2C4%2C5)(H%2C6%2C7) |title=Propanedioic acid |author=NIST Chemistry WebBook}}</ref>
A classical preparation of malonic acid starts from [[chloroacetic acid]]:<ref>{{OrgSynth|title=Malonic acid| vauthors = Weiner N |collvol=2|collvolpages=376|prep=cv2p0376}}</ref>

[[Image:Synthesis of malonic acid.png|thumb|center|650px|Preparation of malonic acid from [[chloroacetic acid]].]]

[[Sodium carbonate]] generates the sodium [[salt (chemistry)|salt]], which is then reacted with [[sodium cyanide]] to provide the sodium salt of [[cyanoacetic acid]] via a [[nucleophilic substitution]]. The [[nitrile]] group can be [[hydrolysis|hydrolyzed]] with [[sodium hydroxide]] to sodium malonate, and acidification affords malonic acid. Industrially, however, malonic acid is produced by hydrolysis of [[dimethyl malonate]] or [[diethyl malonate]].<ref>{{cite patent |country=US |number=2373011 |status=patent |gdate=1945-04-03 |fdate=1942-09-22 | inventor = Britton EC, Ezra M |title=Production of malonic acid |assign1=Dow Chemical Co |class=}}</ref> It has also been produced through [[fermentation]] of [[glucose]].<ref>{{cite patent | title = Recombinant host cells for the production of malonate. | country = US | number = 20200172941| inventor = Dietrich JA | assign1 = Lygos Inc }}</ref>

==Reactions==
Malonic acid reacts as a typical carboxylic acid forming [[amide]], ester, and [[acyl chloride|chloride]] derivatives.<ref>{{cite book |doi=10.1002/0471740039.vec1571 |chapter=Malonic Acid and Derivatives |title=Van Nostrand's Encyclopedia of Chemistry |year=2005 |isbn=0471740039 | veditors = Pollak P, Romeder G |last1=Pollak |first1=Peter |last2=Romeder |first2=Gérard }}</ref> [[Malonic anhydride]] can be used as an intermediate to mono-ester or amide derivatives, while [[malonyl chloride]] is most useful to obtain diesters or diamides.
In a well-known reaction, malonic acid [[condensation reaction|condenses]] with [[urea]] to form [[barbituric acid]]. Malonic acid may also be condensed with [[acetone]] to form [[Meldrum's acid]], a versatile intermediate in further transformations. The esters of malonic acid are also used as a −CH2COOH [[synthon]] in the [[malonic ester synthesis]].

===Briggs–Rauscher reaction===
Malonic acid is a key component in the [[Briggs–Rauscher reaction]], the classic example of an [[Chemical oscillator|oscillating chemical reaction]].<ref>{{cite journal | vauthors = Csepei LI, Bolla C |title=The Effect of Salicylic Acid on the Briggs-Rauscher Oscillating Reaction |url= http://chem.ubbcluj.ro/~studiachemia/issues/chemia2006_2015/Chemia2011_1.pdf |journal=Studia UBB Chemia|volume=1|pages=285–300}}</ref>

===Knoevenagel condensation===
Malonic acid is used to prepare a,b-unsaturated carboxylic acids by condensation and decarboxylation. [[Cinnamic acid]]s are prepared in this way:
:{{chem2|CH2(CO2H)2 + ArCHO -> ArCH\dCHCO2H + H2O + CO2}}
In this, the so-called [[Knoevenagel condensation]], malonic acid condenses with the [[carbonyl]] group of an [[aldehyde]] or [[ketone]], followed by a [[decarboxylation]].
[[Image:KnoevenagelGeneral.png|thumb|center|400px|Z=COOH (malonic acid) or Z=COOR' (malonate ester)]]
When malonic acid is condensed in hot pyridine, the condensation is accompanied by [[decarboxylation]], the so-called [[Doebner modification]].<ref>{{OrgSynth |first1= Peter J. |last1= Jessup |first2= C. Bruce |last2= Petty |first3= Jan |last3= Roos |first4= Larry E. |last4= Overman |author-link4= Larry E. Overman | title = 1-''N''-Acylamino-1,3-dienes from 2,4-Pentadienoic Acids by the Curtius Rearrangement: benzyl ''trans''-1,3-butadiene-1-carbamate | volume = 59 | page = 1 | year = 1979 | doi = 10.15227/orgsyn.059.0001}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.024.0092 |title=Sorbic Acid |journal=Organic Syntheses |date=1944 |volume=24 |page=92|first1=C. F. H. |last1=Allen|first2=J. |last2=VanAllan }}</ref><ref>{{cite journal| vauthors = Doebner O |title=Ueber die der Sorbinsäure homologen, ungesättigten Säuren mit zwei Doppelbindungen|journal=Berichte der Deutschen Chemischen Gesellschaft |year=1902|volume=35|pages=1136–36|doi=10.1002/cber.190203501187 |url = https://zenodo.org/record/1426042}}</ref>
[[Image:Doebner modification.png|center|thumb|600px|The Doebner modification of the Knoevenagel condensation.]]{{clear}}

===Preparation of carbon suboxide===
Malonic acid does not readily form an [[acid anhydride|anhydride]], dehydration gives [[carbon suboxide]] instead:
:{{chem2|CH2(CO2H)2 -> O\dC\dC\dC\dO + 2 H2O}}
The transformation is achieved by warming a dry mixture of [[phosphorus pentoxide]] ({{Chem2|P4O10}}) and malonic acid.<ref>{{cite journal|author-link=Otto Diels|vauthors=Diels O, Wolf B|year=1906|title=Ueber das Kohlensuboxyd. I|url=https://zenodo.org/record/1426170|journal=[[Chemische Berichte|Chem. Ber.]]|volume=39|pages=689–697|doi=10.1002/cber.190603901103}}</ref> It reacts in a similar way to [[malonic anhydride]], forming malonates.<ref>{{cite journal|vauthors=Perks HM, Liebman JF|year=2000|title=Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides|journal=Structural Chemistry|volume=11|issue=4|pages=265–269|doi=10.1023/A:1009270411806|s2cid=92816468 }}</ref>

==Applications==
Malonic acid is a precursor to specialty [[polyester]]s. It can be converted into [[1,3-propanediol]] for use in polyesters and polymers (whose usefulness is unclear though). It can also be a component in [[Alkyd|alkyd resins]], which are used in a number of coatings applications for protecting against damage caused by UV light, oxidation, and corrosion. One application of malonic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process.<ref>{{cite book | vauthors = Facke T, Subramanian R, Dvorchak M, Feng S | chapter = Diethylmalonate blocked isocyanate as crosslinkers for low temperature cure powder coatings. | title = Proceedings of 31st International Waterborene, High-Solids and Powder Coating Symposium | date = February 2004 }}</ref> The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.<ref>{{cite report | vauthors = James S | title = Global Automotive Coatings Market. 2015 Grand View Research Market Report }}</ref>

It is used in a number of manufacturing processes as a high value specialty chemical including the [[Electronics manufacturing services|electronics]] industry, flavors and fragrances industry,<ref name=gsc/> specialty solvents, polymer crosslinking, and pharmaceutical industry. In 2004, annual global production of malonic acid and related diesters was over 20,000 metric tons.<ref>{{Cite web|url = http://www.inchem.org/documents/sids/sids/malonates.pdf|title = Malonic acid diesters|website = Inchem|publisher = UNEP Publications|access-date = 2015-12-11|archive-date = 2017-11-18|archive-url = https://web.archive.org/web/20171118040007/http://www.inchem.org/documents/sids/sids/malonates.pdf|url-status = dead}}</ref> Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications.

In 2004, malonic acid was listed by the US Department of Energy as one of the top 30 chemicals to be produced from biomass.<ref>{{cite report | vauthors = Werpy TA, Holladay JE, White JF | veditors = Werpy TA, Petersen G |date=August 2004 |title=Top Value Added Chemicals From Biomass. Volume I: Results of Screening for Potential Candidates from Sugars and Synthesis Gas |url=https://www.pnnl.gov/main/publications/external/technical_reports/PNNL-14808.pdf |publisher=US Department of Energy |doi=10.2172/926125 |doi-access=free |osti=926125 |osti-access=free }}</ref>

In food and drug applications, malonic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.<ref name=gsc />

Malonic acid is used as a building block chemical to produce numerous valuable compounds,<ref>Hildbrand, S.; Pollak, P. Malonic Acid & Derivatives. March 15, 2001. Ullmann's Encyclopedia of Industrial Chemistry</ref> including the flavor and fragrance compounds gamma-nonalactone, [[cinnamic acid]], and the pharmaceutical compound [[valproate]].

Malonic acid (up to 37.5% w/w) has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts.<ref>{{cite patent | inventor = Netravali AN, Dastidar TG | assign1 = Cornell University | title = Crosslinked native and waxy starch resin compositions and processes for their manufacture. | country = US | number = 9790350 }}</ref><ref name="pmid22944425">{{cite journal | vauthors = Ghosh Dastidar T, Netravali AN | title = 'Green' crosslinking of native starches with malonic acid and their properties | journal = Carbohydrate Polymers | volume = 90 | issue = 4 | pages = 1620–8 | date = November 2012 | pmid = 22944425 | doi = 10.1016/j.carbpol.2012.07.041 }}</ref> Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments.<ref>{{cite report | title = Biodegradable Polymers: Chemical Economics Handbook | date = June 2021 | url = https://ihsmarkit.com/products/biodegradable-polymers-chemical-economics-handbook.html | publisher = IHS Markit }}</ref>

[[Eastman Chemical Company|Eastman]] Kodak company and others use malonic acid and derivatives as a surgical adhesive.<ref>{{cite patent | inventor = Hawkins G, Fassett D | title = Surgical Adhesive Compositions | country = US | number = 3591676 }}</ref>

== Pathology ==
If elevated malonic acid levels are accompanied by elevated [[methylmalonic acid]] levels, this may indicate the metabolic disease [[combined malonic and methylmalonic aciduria]] (CMAMMA). By calculating the malonic acid to methylmalonic acid ratio in blood plasma, CMAMMA can be distinguished from classic [[methylmalonic acidemia]].<ref>{{cite journal | vauthors = de Sain-van der Velden MG, van der Ham M, Jans JJ, Visser G, Prinsen HC, Verhoeven-Duif NM, van Gassen KL, van Hasselt PM | display-authors = 6 | title = A New Approach for Fast Metabolic Diagnostics in CMAMMA | journal = JIMD Reports | volume = 30 | pages = 15–22 | date = 2016 | pmid = 26915364 | pmc = 5110436 | doi = 10.1007/8904_2016_531 | isbn = 978-3-662-53681-0 | veditors = Morava E, Baumgartner M, Patterson M, Rahman S | publisher = Springer | place = Berlin, Heidelberg }}</ref>

==Biochemistry==
Malonic acid is the precursor in [[Fatty acid synthesis#Mitochondrial fatty acid synthesis|mitochondrial fatty acid synthesis]] (mtFASII), in which it is converted to [[malonyl-CoA]] by [[ACSF3|acyl-CoA synthetase family member 3]] (ACSF3).<ref>{{Cite journal |last1=Witkowski |first1=Andrzej |last2=Thweatt |first2=Jennifer |last3=Smith |first3=Stuart |date=2011 |title=Mammalian ACSF3 Protein Is a Malonyl-CoA Synthetase That Supplies the Chain Extender Units for Mitochondrial Fatty Acid Synthesis |journal=Journal of Biological Chemistry |language=en |volume=286 |issue=39 |pages=33729–33736 |doi=10.1074/jbc.M111.291591 |doi-access=free |pmc=3190830 |pmid=21846720}}</ref><ref>{{Cite journal |last1=Bowman |first1=Caitlyn E. |last2=Rodriguez |first2=Susana |last3=Selen Alpergin |first3=Ebru S. |last4=Acoba |first4=Michelle G. |last5=Zhao |first5=Liang |last6=Hartung |first6=Thomas |last7=Claypool |first7=Steven M. |last8=Watkins |first8=Paul A. |last9=Wolfgang |first9=Michael J. |date=2017 |title=The Mammalian Malonyl-CoA Synthetase ACSF3 Is Required for Mitochondrial Protein Malonylation and Metabolic Efficiency |journal=Cell Chemical Biology |language=en |volume=24 |issue=6 |pages=673–684.e4 |doi=10.1016/j.chembiol.2017.04.009 |pmc=5482780 |pmid=28479296}}</ref>

Additionally, the [[coenzyme A]] derivative of malonate, malonyl-CoA, is an important precursor in [[Cytosol|cytosolic]] fatty acid biosynthesis along with [[acetyl CoA]]. Malonyl CoA is formed there from acetyl CoA by the action of [[acetyl-CoA carboxylase]], and the malonate is transferred to an [[acyl carrier protein]] to be added to a fatty acid chain.

Malonic acid is the classic example of a [[Competitive inhibition|competitive inhibitor]] of the [[enzyme]] [[succinate dehydrogenase]] (complex II), in the [[oxidative phosphorylation|respiratory electron transport chain]].<ref name="pardee_potter">{{cite journal | vauthors = Pardee AB, Potter VR | title = Malonate inhibition of oxidations in the Krebs tricarboxylic acid cycle | journal = The Journal of Biological Chemistry | volume = 178 | issue = 1 | pages = 241–250 | date = March 1949 | pmid = 18112108 | doi = 10.1016/S0021-9258(18)56954-4 | doi-access = free }}</ref> It binds to the [[active site]] of the enzyme without reacting, competing with the usual substrate [[Succinic acid|succinate]] but lacking the −CH2CH2− group required for dehydrogenation. This observation was used to deduce the structure of the active site in succinate dehydrogenase. Inhibition of this enzyme decreases cellular respiration.<ref>{{cite journal | vauthors = Potter VR, Dubois KP | title = Studies on the Mechanism of Hydrogen Transport in Animal Tissues : VI. Inhibitor Studies with Succinic Dehydrogenase | journal = The Journal of General Physiology | volume = 26 | issue = 4 | pages = 391–404 | date = March 1943 | pmid = 19873352 | pmc = 2142566 | doi = 10.1085/jgp.26.4.391 }}</ref><ref>{{cite journal |doi=10.1016/0926-6569(64)90182-8 |title=Studies on succinate dehydrogenase |year=1964 | vauthors = Dervartanian DV, Veeger C |journal=Biochimica et Biophysica Acta (BBA) - Specialized Section on Enzymological Subjects |volume=92 |issue=2 |pages=233–247 }}</ref> Since malonic acid is a natural component of many foods, it is present in mammals including humans.<ref>{{cite web |url=https://hmdb.ca/metabolites/HMDB0000691 |title=Metabocard for Malonic acid |website= Human Metabolome Database |access-date=2020-10-06 |date=2020-03-13 }}</ref>

==Related Chemicals==
The fluorinated version of malonic acide is [[difluoromalonic acid]].[https://pubchem.ncbi.nlm.nih.gov/compound/Difluoromalonic-acid]

[[Image:Malonate.png|thumb|Chemical structure of the malonate [[dianion]].]]
Malonic acid is [[Acid#Polyprotic_acids|diprotic]]; that is, it can donate two [[Hydron (chemistry)|protons]] per molecule. Its first [[Dissociation_constant#Acid–base_reactions|<math chem>pK_a</math>]] is 2.8 and the second is 5.7.<ref name=Williams /> Thus the '''malonate''' [[ion]] can be {{chem2|auto=yes|HOOCCH2COO(-)}} or {{chem2|auto=yes|CH2(COO)2(2-)}}. Malonate or '''propanedioate''' [[chemical compound|compounds]] include [[salt (chemistry)|salts]] and [[ester]]s of malonic acid, such as
*[[Diethyl malonate]]
*[[Dimethyl malonate]]
*[[Disodium malonate]]
*[[Malonyl-CoA]]

== References ==
{{reflist}}

== External links ==
*[http://www.aim.env.uea.ac.uk/aim/accent2/inputpage.php Calculator: Water and solute activities in aqueous malonic acid]

{{Navbox linear saturated dicarboxylic acids}}

{{Authority control}}

[[Category:Dicarboxylic acids]]

Ferrous tungstate

2024-08-27T02:26:34Z

Leiem: expand article according to the reference

{{Chembox
| Name = Ferrous tungstate
| OtherNames = [[Iron(II) tungstate]]
| IUPACNames = {{Unbulleted list|Iron(2+) dioxido(dioxo)tungsten [ACD/IUPAC Name]|Tungsten, diolatodioxo-, iron(2+) salt (1:1)
[ACD/Index Name]}}
| Section1 = {{Chembox Identifiers
| CASNo = 20405-35-0
| PubChem=22178528
| ChemSpiderID = 11214118
| DTXSID = DTXSID00623278
| StdInChI=1S/Fe.4O.W/q+2;;;2*-1;
| StdInChIKey = SSWAPIFTNSBXIS-UHFFFAOYSA-N
| SMILES = [O-][W](=O)(=O)[O-].[Fe+2]
}}
| Section2 = {{Chembox Properties
|Formula = FeWO₄
|MolarMass = 303.68 g/mol
}}
| Section3 =
}}

'''Ferrous tungstate''' ({{chem2|FeWO4}}) is an [[inorganic compound]]. It can be synthesized from [[iron(III) chloride]] and [[sodium tungstate]] under hydrothermal conditions, where the presence of L-[[cysteine]] reduces Fe3+ to Fe2+.<ref>{{Cite journal |last1=Zhang |first1=Jian |last2=Zhang |first2=Yan |last3=Yan |first3=Jing-Yi |last4=Li |first4=Shi-Kuo |last5=Wang |first5=Hai-Sheng |last6=Huang |first6=Fang-Zhi |last7=Shen |first7=Yu-Hua |last8=Xie |first8=An-Jian |title=A novel synthesis of star-like FeWO4 nanocrystals via a biomolecule-assisted route |url=https://link.springer.com/article/10.1007/s11051-012-0796-6 |url-access=limited |journal=[[Springer]] |date=2012 |volume=14 |issue=4 |doi=10.1007/s11051-012-0796-6 |language=English}}</ref>

== References ==
<references />

[[Category:Tungstates]]
[[Category:Iron(II) compounds]]

1-Iodohexane

2024-08-08T08:50:30Z

Leiem: /* Synthesis */ Add 1 ref

{{Chembox

| Name = 1-Iodorohexane
| ImageFile = Hexyl iodide.svg
| ImageCaption = 
| IUPACName =
| OtherNames = Hexyl iodide

| Section1 = {{Chembox Identifiers
| CASNo = 638-45-9
| CASNo_Ref = {{Cascite|correct|CAS}}
| PubChem = 12527
| ChemSpiderID = 12010
| EINECS = 211-339-0
| UNII =
| DTXSID = DTXSID2049341
| StdInChI = 1S/C6H13I/c1-2-3-4-5-6-7/h2-6H2,1H3
| StdInChIKey = ANOOTOPTCJRUPK-UHFFFAOYSA-N
| SMILES = CCCCCCI
}}
| Section2 = {{Chembox Properties
|C=6| H=13 | I=1
| Appearance = yellowish liquid
| Density = 1.437 g/cm3
| Solubility = practically insoluble
| MeltingPtC = -75
| BoilingPtC = 181
}}
| Section4 = {{Chembox Structure
| CrystalStruct =
}}
| Section7 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases =
| PPhrases =
}}
| Section6 = {{Chembox Related
| OtherCompounds =
}}
}}
'''1-Iodohexane''' is a chemical compound from the group of aliphatic saturated halogenated hydrocarbons. The chemical formula is {{chem2|CH3(CH2)5I}}.<ref>{{cite web |title=Hexane, 1-iodo- |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=638-45-9 |publisher=[[NIST]] |access-date=8 August 2024}}</ref><ref>{{cite book |last1=Barnes |first1=Ian |last2=Rudzinski |first2=Krzysztof J. |title=Environmental Simulation Chambers: Application to Atmospheric Chemical Processes |date=13 January 2006 |publisher=[[Springer Science & Business Media]] |isbn=978-1-4020-4231-7 |page=202 |url=https://www.google.ru/books/edition/Environmental_Simulation_Chambers_Applic/H5NvQHm4RV4C?hl=en&gbpv=1&dq=1-Iodohexane&pg=PA202&printsec=frontcover |access-date=8 August 2024 |language=en}}</ref>

==Synthesis==
1-Iodohexane can be obtained by reacting [[1-bromohexane]] with [[potassium iodide]].

The compound can also be prepared by reacting [[1-hexanol]], [[iodine]] and [[triphenylphosphine]].<ref>Alberto Hernán-Gómez, Mònica Rodríguez, Teodor Parella, Miquel Costas. Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non-Activated Aliphatic C−H Bonds via Metallocarbene Intermediates. ''Angew Chem Int Ed'', 2019. 58 (39): 13904-13911. {{doi|10.1002/anie.201905986}}.</ref>

==Physical properties==
1-iodohexane is a flammable, difficult to ignite, light-sensitive, colorless to yellowish liquid that is practically insoluble in water.<ref>{{cite book |title=Marine enzymes and specialized metabolism - Part B |date=22 June 2018 |publisher=[[Academic Press]] |isbn=978-0-12-815046-7 |page=212 |url=https://www.google.ru/books/edition/Marine_enzymes_and_specialized_metabolis/m11gDwAAQBAJ?hl=en&gbpv=1&dq=1-Iodohexane&pg=PA212&printsec=frontcover |access-date=8 August 2024 |language=en}}</ref> Copper is added to the compound as a stabilizer.<ref>{{cite web |title=1-Iodohexane |url=https://www.sigmaaldrich.com/RU/en/product/aldrich/238287 |publisher=[[Sigma Aldrich]] |access-date=8 August 2024}}</ref>

==Uses==
The compound is used as an [[alkylating agent]] in [[organic synthesis]].<ref>{{cite web |title=1-Iodohexane {{!}} CAS 638-45-9 {{!}} SCBT - Santa Cruz Biotechnology |url=https://www.scbt.com/p/1-iodohexane-638-45-9 |publisher=[[scbt.com]] |access-date=8 August 2024 |language=en}}</ref> Also, it is used as an intermediate in the production of other chemical compounds such as [[tetradecane]].

==See also==
* [[1-Bromohexane]]
* [[1-Chlorohexane]]
* [[1-Fluorohexane]]

==References==
{{reflist}}

[[Category:Iodoalkanes]]
[[Category:Alkylating agents]]

Paramenthane hydroperoxide

2024-08-02T03:45:41Z

Leiem: The original CAS RN is the isomer mixture of PMHP

{{Chembox
| Name = Paramenthane hydroperoxide
| ImageFile = 5-Methyl-2-(1-methylethyl)cyclohexyl hydroperoxide.svg
| ImageSize = 150px
| IUPACName = 2-hydroperoxy-4-methyl-1-propan-2-ylcyclohexane
| OtherNames = Menthyl hydroperoxide
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 39811-34-2
| PubChem = 117329
| EC_number = 247-987-6
| ChemSpiderID = 104850
| StdInChI=1S/C10H20O2/c1-7(2)9-5-4-8(3)6-10(9)12-11/h7-11H,4-6H2,1-3H3
| StdInChIKey = OZTWDFWAMMUDHQ-UHFFFAOYSA-N
| SMILES = CC1CCC(C(C1)OO)C(C)C
}}
|Section2={{Chembox Properties
| C=10 | H=20 | O=2
| Appearance = Light yellow liquid (50% solution)
| Odor = Distinct
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://www.lyondellbasell.com/techlit/techlit/mch/msds/GlidoxTM300.pdf.pdf MSDS]
| MainHazards = Oxidizing, flammable, causes severe burns, explosive decomposition possible above 60°C<ref name="lyondellbasell">[http://www.lyondellbasell.com/techlit/techlit/mch/msds/GlidoxTM300.pdf.pdf Lyondellbasell MSDS]</ref>
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|242|314|373}}
| PPhrases = {{P-phrases|210|220|234|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|314|321|363|370+378|403+235|405|411|420|501}}
}}
}}
'''Paramenthane hydroperoxide''' ('''PMHP''') is an [[organic peroxide]] with a distinctive odor. It is used on an industrial scale as a [[polymerization]] initiator for [[emulsion polymerization]]s. It is usually sold in a light yellow liquid [[Solution (chemistry)|solution]]s of about 50% strength.<ref>SASOL (2009). "EC-safety data sheet: paramenthane hydroperoxide (PMHP)," ''Product MSDS'', p. 1.</ref>

== References ==
{{reflist}}

[[Category:Organic peroxides]]
[[Category:Monoterpenes]]

{{organic-compound-stub}}

Paramenthane hydroperoxide

2024-08-02T03:42:32Z

Leiem: Wrong structure

{{Chembox
| Name = Paramenthane hydroperoxide
| ImageFile = 5-Methyl-2-(1-methylethyl)cyclohexyl hydroperoxide.svg
| ImageSize = 150px
| IUPACName = 2-hydroperoxy-4-methyl-1-propan-2-ylcyclohexane
| OtherNames = Menthyl hydroperoxide
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 26762-92-5
| PubChem = 117329
| EC_number = 247-987-6
| ChemSpiderID = 104850
| StdInChI=1S/C10H20O2/c1-7(2)9-5-4-8(3)6-10(9)12-11/h7-11H,4-6H2,1-3H3
| StdInChIKey = OZTWDFWAMMUDHQ-UHFFFAOYSA-N
| SMILES = CC1CCC(C(C1)OO)C(C)C
}}
|Section2={{Chembox Properties
| C=10 | H=20 | O=2
| Appearance = Light yellow liquid (50% solution)
| Odor = Distinct
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://www.lyondellbasell.com/techlit/techlit/mch/msds/GlidoxTM300.pdf.pdf MSDS]
| MainHazards = Oxidizing, flammable, causes severe burns, explosive decomposition possible above 60°C<ref name="lyondellbasell">[http://www.lyondellbasell.com/techlit/techlit/mch/msds/GlidoxTM300.pdf.pdf Lyondellbasell MSDS]</ref>
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|242|314|373}}
| PPhrases = {{P-phrases|210|220|234|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|314|321|363|370+378|403+235|405|411|420|501}}
}}
}}
'''Paramenthane hydroperoxide''' ('''PMHP''') is an [[organic peroxide]] with a distinctive odor. It is used on an industrial scale as a [[polymerization]] initiator for [[emulsion polymerization]]s. It is usually sold in a light yellow liquid [[Solution (chemistry)|solution]]s of about 50% strength.<ref>SASOL (2009). "EC-safety data sheet: paramenthane hydroperoxide (PMHP)," ''Product MSDS'', p. 1.</ref>

== References ==
{{reflist}}

[[Category:Organic peroxides]]
[[Category:Monoterpenes]]

{{organic-compound-stub}}

Diiodine tetroxide

2024-08-01T02:39:52Z

Leiem: CAS RN

{{Chembox
| IUPACName = iodosyl iodate
|Section1={{Chembox Identifiers
| PubChem = 54579881
| StdInChI=1S/I2O4/c3-1-6-2(4)5
| StdInChIKey = XHTWXUOEQMOFEJ-UHFFFAOYSA-N
| SMILES = O=IOI(=O)=O
| CASNo = 1024652-24-1
| CASNo_Ref = {{cascite|correct|CAS}}
}}
|Section2={{Chembox Properties
| Density = 2.57
}}
|Section8={{Chembox Related
}}
}}

'''Diiodine tetraoxide''', I2O4, is a chemical compound of [[oxygen]] and [[iodine]]. It belongs to the group of [[Iodine oxide|iodine oxides]].

==Synthesis==

The oxide is formed by the reaction of hot concentrated sulfuric acid on iodic acid for several days.<ref name=hwic>{{cite book |title=Holleman-Wiberg inorganic chemistry |date=2001 |publisher=Academic |location=San Diego, Calif. London |isbn=0123526515|pages=465–466}}</ref>
:{{chem2|3HIO3 -> I2O4 + HIO4 + H2O}}

It is formed from diiodine pentoxide and iodine in concentrated [[sulfuric acid]] or [[bis(iodosyl) sulphate]] (IO)2SO4 added to water :<ref name="fjell">{{cite journal |last1=Fjellvåg |first1=Helmer |last2=Kjekshus |first2=Arne |last3=Persson |first3=Ingmar |last4=Figgis |first4=Brian N. |last5=Liaaen-Jensen |first5=Synnøve |last6=Balzarini |first6=Jan |last7=Fransson |first7=Bengt |last8=Ragnarsson |first8=Ulf |last9=Francis |first9=George W. |title=The Crystal Structure of I2O4 and its Relations to Other Iodine--Oxygen-Containing Compounds. |journal=Acta Chemica Scandinavica |date=1994 |volume=48 |pages=815–822 |doi=10.3891/acta.chem.scand.48-0815}}</ref>

:{{Chem2|4(IO)2SO4 + 4H2O -> I2O4 + I2 + 4H2SO4}}

==Physical properties==

Diiodine tetraoxide is a yellow, granular powder. At temperatures above 85 °C it decomposes to [[diiodine pentoxide]] and iodine:<ref name=hwic/>

:{{chem2|5I2O4 -> 4I2O5 + I2}}

This process is even faster at 135 °C. It dissolves in hot water to form [[iodate]] and [[iodide]].<ref name=hwic/> Structurally, the compound is an '''iodyl iodite''' O2I-OIO (iodine(V,III) oxide)<ref name=hwic/> with bent IVO2 units (I–O distances 1.80 and 1.85 Å; ∠OIO angle 97°) and bent IIIIO2 units (IO distances 1.93 Å, OIO angle 95.8°). Both units are linked via I—O—I bridges to form polymeric zigzag chains (I2O4)x.<ref name=hwic/>

Diiodine tetraoxide has a [[monoclinic]] crystal structure with the [[space group]] ''P''21/''c'' (space group number 14). Unit cell dimensions are a = 8.483 b = 6.696 c = 8.333 Å and β = 124.69°. Unit cell volume = 389.15 Å3. Z = 4. Density is 2.57 Mg/m3<ref name="fjell"/><ref>{{cite journal |last1=Wu |first1=Zhongqing |last2=Kalia |first2=Rajiv K. |last3=Nakano |first3=Aiichiro |last4=Vashishta |first4=Priya |title=First-principles calculations of the structural and dynamic properties, and the equation of state of crystalline iodine oxides I2O4, I2O5, and I2O6 |journal=The Journal of Chemical Physics |date=28 May 2011 |volume=134 |issue=20 |doi=10.1063/1.3590278}}</ref>

==Reactions==
Diiodine tetroxide oxidises hydrochloric acid :<ref>{{cite book |title=Advances in Inorganic Chemistry and Radiochemistry |date=1 January 1963 |publisher=Academic Press |isbn=978-0-08-057854-5 |page=77-78 |url=https://books.google.com/books?id=pRXIwIV-hB8C |language=en}}</ref>

:{{chem2|I2O4 + 8H+ + 8Cl− -> 2ICl + 4H2O + 3Cl2}}

==References==

<ref>{{cite book |isbn=978-1482208689 |page=S.4-67|title=CRC Handbook of Chemistry and Physics|publisher=CRC Press |year=2014|editor=William M. Haynes}}</ref>
<references/>

[[Category:Iodine compounds]]

Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate

2024-07-30T18:07:31Z

Leiem: added Category:Cyanoacetate esters using HotCat

{{Short description|Organic compound used in sunscreen}}

{{Chemical infobox
| Name = Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate
| ImageFile = [[File:Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate.png|frameless]]
| OtherNames = {{Unbulleted list|Mexoryl 400|Colipa No. S 87|C-1701 B_C_3|C-1701 Merocyanine}}
| IUPACName =
| IUPACNames = {{Unbulleted list|2-ethoxyethyl (2Z)-2-cyano-2-[3-(3-methoxypropylamino) cyclohex-2-en-1-ylidene]acetate|2-ethoxyethyl 2-cyano-2-[(1Z)-3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene]acetate}}
| Section1 = {{Chembox Identifiers
| Identifiers_ref =

| index_label =
| index1_label =
| indexlist_caption =
| index_comment =
| index1_comment =

| CASNo = 1419401-88-9
| CASNo_Comment =
| CASNo1 =
| CASNo1_Comment =
| CASNoOther =

| ChEBI =
| ChEBI_Comment =
| ChEBI1 =
| ChEBI1_Comment =
| ChEBIOther =

| ChEMBL =
| ChEMBL_Comment =
| ChEMBL1 =
| ChEMBL1_Comment =
| ChEMBLOther =

| ChemSpiderID =
| ChemSpiderID_Comment =
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| ChemSpiderID1_Comment =
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| DrugBank =
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| IUPHAR_ligand =
| IUPHAR_ligand_Comment =
| IUPHAR_ligand1 =
| IUPHAR_ligand1_Comment =
| IUPHAR_ligand_Other =

| KEGG =
| KEGG_Comment =
| KEGG1 =
| KEGG1_Comment =
| KEGGOther =

| PubChem = 71226339
| PubChem_Comment =
| PubChem1 =
| PubChem1_Comment =
| PubChemOther =

| SMILES = CCOCCOC(=O)C(=C1CCCC(=C1)NCCCOC)C#N
| SMILES_Comment =
| SMILES1 =
| SMILES1_Comment =
| SMILESOther =
| Jmol =
| Jmol1 =

| StdInChI =
| StdInChI_Comment =
| StdInChIKey =

| InChI = 1S/C17H26N2O4/c1-3-22-10-11-23-17(20)16(13-18)14-6-4-7-15(12-14)19-8-5-9-21-2/h12,19H,3-11H2,1-2H3/b16-14-
| InChI_Comment =
| InChIKey = NPNDSRGIZUPLNP-PEZBUJJGSA-N
| InChI1 =
| InChI1_Comment =
| InChIKey1 =
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| UNII =
| UNII_Comment =
| UNII1 =
| UNII1_Comment =
| UNIIOther =

| DTXSID = DTXSID901019869
| DTXSIDOther =

| 3DMet =

| EC_number = 700-860-3
| EC_number_Comment =
| EINECS =

| RTECS =
| RTECSOther =

| Abbreviations =
| Beilstein =
| Gmelin =
| MeSHName =
| UNNumber =
}}
| Section2 = {{Chembox Properties
| Properties_ref =
| Formula =
| Formula_ref =
| Formula_Comment =
| C=17 | H=26 | N=2 | O=4
| Formula_Charge =
| MolarMass =
| MolarMassRound =
| MolarMass_ref =
| MolarMass_notes =
| Appearance = Yellow solid in the form of powder or small chunks
| Odor = | Odour =
| Density =
| MeltingPt =
| MeltingPtC = 85-120
| MeltingPtF =
| MeltingPtK =
| MeltingPt_ref =
| MeltingPt_notes =
| BoilingPt =
| BoilingPtC = 306-315
| BoilingPtF =
| BoilingPtK =
| BoilingPt_ref =
| BoilingPt_notes =
| CriticalTP =
| SublimationConditions =
| Solubility =
| SolubilityProduct =
| SolubilityProductAs =
| SolubleOther =
| Solvent =
| Solubility1 = 13% w/w
| Solvent1 = Ethanol
| Solubility2 =
| Solvent2 =
| Solubility3 =
| Solvent3 =
| Solubility4 =
| Solvent4 =
| Solubility5 =
| Solvent5 =
| Solubility6 =
| Solvent6 =
| CMC =
| HLB =
| LogP = 1.7
| VaporPressure =
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa = 13.3
| pKb =
| ConjugateAcid =
| ConjugateBase =
| IsoelectricPt =
| ElectricalResistivity =
| LambdaMax = 385
| Absorbance =
| BandGap =
| ElectronMobility =
| SpecRotation =
| MagSus =
| ThermalConductivity =
| RefractIndex =
| Viscosity =
| CriticalRelativeHumidity =
| Dipole =
| OrbitalHybridisation =
| SpecificSurfaceArea =
| PoreVolume =
| AveragePoreSize =
}}
}}
'''Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate''' ([[International Nomenclature of Cosmetic Ingredients|INCI]]) is an [[organic compound]] used in [[sunscreen]]s to absorb [[UVA radiation]]. It is marketed as Mexoryl 400 by [[L'Oréal]]. MCE has an absorption maximum of 385 nm, which is in the long-wave UVA range ([[UVA radiation|UVA1]], 360−400 nm).<ref name=":0">{{cite web |title=Scientific Committee on Consumer Safety |url=https://health.ec.europa.eu/system/files/2021-08/sccs_o_227_0.pdf |website=europa.eu |access-date=28 July 2024}}</ref><ref>{{Cite journal |last1=Marionnet |first1=Claire |last2=de Dormael |first2=Romain |last3=Marat |first3=Xavier |last4=Roudot |first4=Angélina |last5=Gizard |first5=Julie |last6=Planel |first6=Emilie |last7=Tornier |first7=Carine |last8=Golebiewski |first8=Christelle |last9=Bastien |first9=Philippe |last10=Candau |first10=Didier |last11=Bernerd |first11=Françoise |date=January 2022 |title=Sunscreens with the New MCE Filter Cover the Whole UV Spectrum: Improved UVA1 Photoprotection In Vitro and in a Randomized Controlled Trial |url=https://doi.org/10.1016/j.xjidi.2021.100070 |journal=[[JID Innovations]] |volume=2 |issue=1 |pages= |doi=10.1016/j.xjidi.2021.100070 |issn=2667-0267 |pmc=8762479 |pmid=35072138}}</ref><ref>{{Cite journal |last1=Aguilera |first1=José |last2=Gracia-Cazaña |first2=Tamara |last3=Gilaberte |first3=Yolanda |date=2023-10-01 |title=New developments in sunscreens |url=https://doi.org/10.1007/s43630-023-00453-x |journal=Photochemical & Photobiological Sciences |language=en |volume=22 |issue=10 |pages=2473–2482 |doi=10.1007/s43630-023-00453-x |pmid=37543534 |issn=1474-9092}}</ref><ref>{{Cite journal |last1=Bernerd |first1=Françoise |last2=Passeron |first2=Thierry |last3=Castiel |first3=Isabelle |last4=Marionnet |first4=Claire |date=January 2022 |title=The Damaging Effects of Long UVA (UVA1) Rays: A Major Challenge to Preserve Skin Health and Integrity |journal=International Journal of Molecular Sciences |language=en |volume=23 |issue=15 |pages=8243 |doi=10.3390/ijms23158243 |doi-access=free |issn=1422-0067 |pmc=9368482 |pmid=35897826}}</ref><ref>{{Cite web |last=PubChem |title=2-ethoxyethyl (2Z)-2-cyano-2-[3-(3-methoxypropylamino)cyclohex-2-en-1-ylidene]acetate |url=https://pubchem.ncbi.nlm.nih.gov/compound/71226339 |access-date=2024-07-30 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> Like Mexoryl SX ([[Ecamsule]]) and Mexoryl XL ([[Drometrizole trisiloxane]]), it is used exclusively in products manufactured by L'Oréal.<ref>{{Cite web |date=2022-05-24 |title=L'Oréal Breaks the Ultra-long UVA Code with UVMune 400 |url=https://www.cosmeticsandtoiletries.com/formulas-products/sun-care/news/22249181/loreal-loral-breaks-the-ultralong-uva-code-with-uvmune-400 |access-date=2024-07-28 |website=Cosmetics & Toiletries |language=en-us}}</ref> MCE was developed by L'Oréal and [[BASF]].<ref>{{Cite web |date=2024-06-10 |title=La Roche-Posay UVMune 400: Science and Review |url=https://labmuffin.com/la-roche-posay-uvmune-400-science-and-review/ |access-date=2024-07-28 |website=Lab Muffin Beauty Science |language=en-US}}</ref>

In 2019, MCE was approved for use up to a maximum concentration of 3% as a UV filter in cosmetics in the [[European Union|EU]].<ref name=":0" /> It is not currently recognised or approved by the [[Food and Drug Administration|FDA]].

== Properties ==
MCE is a yellow solid in the form of powder or small chunks.<ref name=":0" /> At 25°C, it is soluble in [[phenoxyethanol]], dimethyl capramide, [[ethoxydiglycol]], dimethyl isosorbide, and alcohol ([[ethanol]]), which are ingredients used in cosmetics.<ref name=":0" /><ref>{{Cite web |last=PubChem |title=Phenoxyethanol |url=https://pubchem.ncbi.nlm.nih.gov/compound/31236 |access-date=2024-07-29 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite web |last=PubChem |title=N,N-Dimethyldecanamide |url=https://pubchem.ncbi.nlm.nih.gov/compound/26690 |access-date=2024-07-29 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite web |last=PubChem |title=Diethylene Glycol Monoethyl Ether |url=https://pubchem.ncbi.nlm.nih.gov/compound/8146 |access-date=2024-07-29 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite web |last=PubChem |title=Dimethyl isosorbide |url=https://pubchem.ncbi.nlm.nih.gov/compound/62990 |access-date=2024-07-29 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref><ref>{{Cite journal |last=Lachenmeier |first=Dirk W |date=2008-11-13 |title=Safety evaluation of topical applications of ethanol on the skin and inside the oral cavity |journal=Journal of Occupational Medicine and Toxicology |language=en |volume=3 |issue=1 |pages=26 |doi=10.1186/1745-6673-3-26 |doi-access=free |issn=1745-6673 |pmc=2596158 |pmid=19014531}}</ref>

It is considered a [[Cyclic compound|cyclic]] [[merocyanine]].<ref>{{Cite journal |last=Winkler |first=Barbara |last2=Hoeffken |first2=Hans Wolfgang |last3=Eichin |first3=Kai |last4=Houy |first4=Wolfgang |date=2014-03-05 |title=A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure |url=https://www.sciencedirect.com/science/article/pii/S0040403914001592 |journal=Tetrahedron Letters |volume=55 |issue=10 |pages=1749–1751 |doi=10.1016/j.tetlet.2014.01.113 |issn=0040-4039}}</ref>

== References ==
<references />

[[Category:Sunscreening agents]]
[[Category:Cyanoacetate esters]]

{{Organic-compound-stub}}

Ethyl cyanohydroxyiminoacetate

2024-07-30T18:07:23Z

Leiem: −Category:Nitriles; ±Category:Carboxylate esters→Category:Cyanoacetate esters using HotCat

{{Chembox

| ImageFile = Ethyl cyanohydroxyiminoacetate.svg
| ImageSize = 150px
| ImageAlt =

| PIN = Ethyl (''2Z'')-2-cyano-2-(hydroxyimino)acetate
| OtherNames = Oxyma

| Section1 = {{Chembox Identifiers
| CASNo = 3849-21-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2PHR89MH6P
| PubChem = 6399475
| SMILES =CCOC(=O)/C(=N\O)/C#N
}}
| Section2 = {{Chembox Properties
| Formula = C5H6N2O3
| MolarMass = 142,11 g·[[Mole (unit)|mol]]−1
| Appearance = white powder
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Ethyl cyanohydroxyiminoacetate''' (oxyma) is the [[oxime]] of [[ethyl cyanoacetate]] and finds use as an additive for [[carbodiimide]]s, such as [[dicyclohexylcarbodiimide]] (DCC) in peptide synthesis. It acts as a neutralizing reagent for the [[basicity]] or [[nucleophilicity]] of the DCC due to its pronounced acidity ([[Acid dissociation constant|pKa]] 4.60) and suppresses base catalyzed [[side reaction]]s, in particular [[racemization]].<ref name="Albericio">{{citation|surname1=Subirós-Funosas, R.|author2= Prohens, R.|author3= Barbas, R.|author4= El-Faham, A.|author5= Albericio, F.|periodical=Chem. Eur. J.|title=Oxyma: An efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion|volume=15|issue=37|pages=9394–9403|date= 2009|doi=10.1002/chem.200900614|pmid=19575348}}</ref>

== Production ==
Ethyl cyanohydroxyiminoacetate is obtained in the reaction of [[ethyl cyanoacetate]] and [[nitrous acid]] (from [[sodium nitrite]] and [[acetic acid]]) in 87% [[Yield (chemistry)|yield]].<ref name="Conrad" >{{citation|author1=Conrad, M.|author2=Schulze, A.|periodical=[[Chem. Ber.]]|title=Über Nitroso-cyanessigsäure-Derivate|volume=42|issue=1|pages=735–742|date= 1909|language=German|doi=10.1002/cber.190904201117|url=https://zenodo.org/record/1426329}}</ref>

[[File:Hydroxyiminocyanessigsäureethylester Synthese.svg|400px|center|Synthese von Hydroxyiminocyanessigsäureethylester]]

Because of the rapid hydrolysis of the ester, the reaction should be carried out at pH 4.5, in buffered [[phosphoric acid]] the product can even be obtained in virtually quantitative yield.<ref name="e-EROS" >{{cite encyclopedia|author1=Albericio, F.|author2=Subirós-Funosas, R.|chapter=Ethyl 2-Cyano-2-(hydroxyimino)acetate|date= 2012|doi=10.1002/047084289X.rn01377|title=Encyclopedia of Reagents for Organic Synthesis|isbn=978-0471936237}}</ref>

The compound can be purified by [[Recrystallization (chemistry)|recrystallization]] from [[ethanol]]<ref name="e-EROS" /> or [[ethyl acetate]].<ref>{{Cite patent|country = US|number =5166394 |title=Coupling reagent for peptide synthesis |pubdate =1992-11-2 |fdate =1991-5-21 |invent1 = Breipohl, G.|invent2= König, W. | assign =Hoechst AG}}</ref>

Compared with the [[benzotriazole]] derivatives 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) (which are widely used as peptide-linking reagents but are explosive), ethyl cyanohydroxyiminoacetate exhibits a markedly slowed thermal [[decomposition]] on heating.<ref name="Albericio" />

== Properties ==
Ethyl cyanohydroxyiminoacetate is a white solid which is soluble in many solvents common in the synthesis of peptides, such as [[dichloromethane]] or [[dimethylformamide]] (DMF). In crystalline form, the compound is present as an [[oxime]], whereas it exists as a salt or in a strongly basic solution predominantly as a [[tautomer]]ic nitrosoisomer in anionic form.<ref name="Aldrichimica" />

== Applications ==
Owing to the simple preparative accessibility, the uncritical behavior at temperatures below 80 °C and in particular because of the high yields and the low [[racemization]] of the peptides obtained, ethyl cyanohydroxyiminoacetate has now become widely used as an additive in peptide syntheses.<ref name="Albericio" /><ref name="Aldrichimica" >{{citation|author1=Subirós-Funosas, R.|author2= Khattab, S.N.|author3= Nieto-Rodriguez, L.|author4=El-Faham, A.|author5= Albericio, F.|periodical=Aldrichimica Acta|title=Advances in acylation methodologies enabled by Oxyma-based reagents|volume=46|issue=1|pages=21–41|date= 2013|url=http://www.sigmaaldrich.com/ifb/acta/v46/acta-vol46-2013.html#22}}</ref><ref>{{cite web|title=Coupling Reagents Bachem|trans-title=|website=Bachem.com|publisher=Global Marketing, Bachem Group|url=https://www.bachem.com/fileadmin/user_upload/pdf/Monographs/Coupling_Reagents.pdf|format=PDF; 1,9 MB|accessdate=2016-10-10|archiveurl=|archivedate=|last=|date=2015|language=|pages=|quote=}}</ref>

Ethyl cyanohydroxyiminoacetate can be used as a coupling additive in the conventional peptide linking in solution, as in automated Merrifield synthesis on a ''[[solid-phase peptide synthesis]]'', together with coupling reagents such as carbodiimides (for example [[dicyclohexylcarbodiimide]] (DCC)), [[diisopropylcarbodiimide]] (DIC)<ref>{{citation|author1=El-Faham, A.|author2=Al Marhoon, Z.|author3=Abdel-Megeed, A.|author4= Albericio, F.|periodical=Molecules|title=OxymaPure/DIC: An Efficient Reagent for the Synthesis of a Novel Series of 4-[2-(2-Acetylaminophenyl)-2-oxo-acetylamino] Benzoyl Amino Acid Ester Derivatives|volume=18|issue=12|pages=14747–14759|date= 2013|doi=10.3390/molecules181214747|pmid=24288002|pmc=6269765|doi-access=free}}</ref> or the water-soluble [[1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide|1-ethyl-3-(3-dimethylaminopropyl)carbodiimide]] (EDCI)).<ref name="OrgSynth">{{OrgSynth|prep=v90p0306 |author1=Subirós-Funosas, R.| author2=El-Faham, A. | author3 = Albericio, F. |title=Low-epimerization Peptide Bond Formation with Oxyma Pure: Preparation of Z-L-Phg-Val-OMe |year=2013 |volume=90 |pages=306–315 |doi=10.15227/orgsyn.090.0306 }}</ref>

[[File:Dipeptidsynthese mit Oxyma.svg|500px|center|Dipeptidsynthese mit Oxyma]]

For example, the stepwise liquid-phase synthesis of the [[dipeptide]] Z-''L''-Phg-''L''-Val-OMe yields the ''LL''-product with 81-84% which is free from racemic DL dipeptide, using From N-protected Z-''L''-α-[[phenylglycine]] (with the [[benzyloxycarbonyl group]], Z group) and L-valine methyl ester with the coupling reagent DIC and the additive ethyl cyanohydroxyiminoacetate.<ref name="OrgSynth" />

More recently, a variety of derivatives of ethyl cyanohydroxyiminoacetate (Oxyma) have been developed as acylation reagents,<ref>{{citation|author1=El-Faham, A.|author2=Albericio, F.|periodical=Chem. Rev.|title=Peptide coupling reagents, more than a letter soup|volume=111|issue=11|pages=6557–6602|date= 2011|doi=10.1021/cr100048w|pmid=21866984}}</ref> such as Fmoc-oxyma for the transfer of the fluorenylmethoxycarbonyl protective group<ref>{{citation|author1=Khattab, S.N.|author2=Subirós-Funosas, R.|author3=El-Faham, A. |author4 =Albericio, F.|periodical=Eur. J. Org. Chem.|title=Oxime Carbonates: Novel Reagents for the Introduction of Fmoc and Alloc Protecting Groups, Free of Side Reactions|volume=2010|issue=17|pages=3275–3280|date= 2010|doi=10.1002/ejoc.201000028}}</ref>

[[File:Synthese von Fmoc-Oxyma.svg|500px|center|Fmoc-Oxyma-Synthese]]

or the coupling reagent [[Peptide synthesis#/Triazoles|COMU]] which is readily soluble as a dimethylmorpholine-uronium salt and which, like Oxyma, is superior to the standard additive HOBt for the suppression of racemization and acylation efficiency and is comparable to HOAt without presenting an explosion risk such as the benzotriazoles.<ref name="Aldrichimica" />

With water-soluble derivatives of ethyl cyanohydroxyiminoacetate (glyceroacetonide-oxyma) as additive and DIC as coupling reagent even in weakly basic aqueous solutions the linking of protected amino acids to oligopeptides is possible with a yield of 95% and a diastereomeric excess of> 99% using the model substances Z-''L''-Phg-OH and ''L''-H-Pro-NH2.<ref>{{citation|author1=Wang, Q.|author2=Wang, Y.|author3=Kurosu, M.|periodical=Org. Lett.|title=A new Oxyma derivative for nonracemizable amide-forming reactions in water|volume=14|issue=13|pages=3372–3375|date=2012|doi=10.1021/ol3013556|pmid=22697488|pmc=3431018}}</ref>

[[File:Dipeptidsynthese mit Glyceroacetonid-Oxyma.svg|500px|center|Dipeptidsynthese mit Glyceroacetonid-Oxyma]]

In the coupling of amino acids, frequently occurring secondary reactions largely suppressed, which would be the formation of symmetrical [[acid anhydrides]], racemization and [[epimerization]] and the cyclization to [[oxazolinones]] or - especially for dipeptides - to 2,5-[[diketopiperazine]]s.

== References ==
{{Reflist}}

[[Category:Oximes]]
[[Category:Cyanoacetate esters]]
[[Category:Reagents for biochemistry]]
[[Category:Reagents for organic chemistry]]
[[Category:Ethyl esters]]

Category:Cyanoacetate esters

2024-07-30T18:06:10Z

Leiem: added Category:Carboxylate esters using HotCat

[[Category:Nitriles]]
[[Category:Carboxylate esters]]

Ethyl cyanoacetate

2024-07-30T18:06:07Z

Leiem: −Category:Nitriles; ±Category:Carboxylate esters→Category:Cyanoacetate esters using HotCat

{{Chembox

| ImageFile = Ethyl cyanoacetate.svg
| ImageSize = 200px
| ImageAlt =

| PIN = Ethyl cyanoacetate
| OtherNames =

| Section1 = {{Chembox Identifiers
| CASNo = 105-56-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X9N006U0F8
| PubChem = 7764
| UNNumber = 3276 2666
| EC_number = 203-309-0
| ChemSpiderID = 13856579
| StdInChI = 1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
| StdInChIKey = ZIUSEGSNTOUIPT-UHFFFAOYSA-N
| SMILES = CCOC(=O)CC#N
}}
| Section2 = {{Chembox Properties
| C=5 | H=7 | N=1 | O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
| MagSus = -67.3·10−6 cm3/mol
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|319|332}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|322|330|337+313|363|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H=1
| NFPA-F=1
| NFPA-R=1
}}
}}

'''Ethyl cyanoacetate''' is an [[organic compound]] that contains a [[carboxylate ester]] and a [[nitrile]]. It is a colourless<ref>{{RömppOnline|ID=RD-03-03030|Name=Cyanessigsäureester|Datum=2016-06-15}}</ref> liquid with a pleasant odor. This material is useful as a starting material for synthesis due to its variety of functional groups and chemical reactivity.<ref>{{cite book |doi=10.1002/047084289X.re055|chapter=Ethyl Cyanoacetate|title=Encyclopedia of Reagents for Organic Synthesis|year=2001|last1=Freeman|first1=Fillmore|isbn=0471936235}}</ref>

==Production==
Ethyl cyanoacetate may be prepared in various ways:
*[[Kolbe nitrile synthesis]] using [[ethyl chloroacetate]] and [[sodium cyanide]].<ref name="Org. Synth.">{{OrgSynth|Kurzcode=cv1p0254 |author=J. K. H. Inglis |title=Ethyl Cyanoacetate |Jahrgang=1928 |Volume=8 |Seiten=74 |ColVol=1 |ColVolSeiten=254 |doi=10.15227/orgsyn.008.0074 }}</ref>
*[[Fischer esterification]] of [[cyanoacetic acid]] with [[ethanol]] in the presence of a strong [[mineral acids]] (e.g. concentrated [[sulfuric acid]]). The cyanoacetic acid can be prepared via Kolbe nitrile synthesis using sodium chloroacetate and sodium cyanide.<ref name="Org. Synth."/>
*Reaction of the sodium cyanoacetate with [[ethyl bromide]] in an aqueous–organic two-phase system in the presence of a [[phase transfer catalyst]].<ref>{{cite patent |country=EP |number=1028105 |status= application |pubdate= 2000-08-16 |invent1= Hanselmann, Paul |invent2= Hildebrand, Stefan |assign1= Lonza AG |title= Process for the preparation of cyanoacetic esters }}</ref>
*[[Oxidation]] of 3-ethoxypropionitrile, an [[ether]], with oxygen under pressure in the presence of [[cobalt(II) acetate]] tetrahydrate as catalyst and [[N-hydroxyphthalimide|''N''-hydroxyphthalimide]] as a radical generator.<ref>{{cite patent |country=EP |number=1208081 |status= patent |gdate= 2004-04-14 |invent1= Hanselmann, Paul |invent2= Hildebrand, Stefan |assign1= Lonza AG |title= Method for producing cyanoacetic acid esters }}</ref>

==Properties==

===Physical properties===
[[File:Vapour pressure cyano acetic acid ethyl ester.svg|thumb|right|Vapour pressure of ethyl cyanoacetate]]

The vapor pressure follows the [[Antoine equation]] log10(P) = A−(B/(T+C)) (P in bar, T in K) with A = 7.46724, B = 3693.663 and C = 16.138 in the temperature range from 341 to 479 K<ref name="Stull">{{cite journal |last= Stull |first= D.R. |title= Vapor Pressure of Pure Substances Organic Compounds |journal= Ind. Eng. Chem. |volume= 39 |issue= 4 |year= 1947 |pages= 517–540 |doi= 10.1021/ie50448a022 }}</ref> Two [[Polymorphism (materials science)|polymorphic forms]] occur.<ref name="Khodzhaeva">Khodzhaeva, M.G.; Bugakov, Yu.V.; Ismailov, T.S.: ''Heat capacity and thermodynamic functions of ethyl cyanoacetate'' in Khim.-Farm. Zhur. 21 (1987) 760-762, [[DOI:10.1007/BF00872889]].</ref>{{full citation needed|date=June 2016}} Below −111 °C, the crystal form II is dominant.<ref name="Khodzhaeva"/> Above this temperature, the crystal form I is formed which melts at −22 °C.<ref name="GESTIS">{{GESTIS|ZVG=38010|CAS=105-56-6 |Date=3 March 2011}}</ref> The [[heat capacity]] at 25 °C is 220.22 J K−1 mol−1.<ref name="Khodzhaeva"/>

=== Chemical properties ===
With its three different reactive centers—nitrile, ester, acidic [[Methylene bridge|methylene]] site—ethyl cyanoacetate is a versatile synthetic building block for a variety of functional and pharmacologically active substances. It contains an acidic methylene group, flanked by both the nitrile and [[carbonyl]], and so can be used in condensation reactions like the [[Knoevenagel condensation]] or the [[Michael addition]]. This reactivity is similar to that of [[ester]]s of [[malonic acid]]. As an example of reactivity at the nitrile, [[diethyl malonate]] is obtained from cyanoacetic acid ethyl ester by reaction with ethanol in the presence of [[strong acids]].<ref name="Org. Synth." /> Heating in the presence of [[sodium ethoxide]] forms the [[Dimer (chemistry)|dimeric]] 3-amino-2-cyano-2-pentendiaciddiethylester.<ref>{{cite journal |first1= V. A. |last1= Dorokhov |first2= S. V. |last2= Baranin |first3= A. |last3= Dib |first4= V. S. |last4= Bogdanov |title= 'Codimers' of ''N''-(pyrid-2-yl) amides and ethyl cyanoacetate |journal= Russ. Chem. Bull. |volume= 41 |issue= 2 |pages= 287–291 |year= 1992 |doi= 10.1007/bf00869516 |s2cid= 95912295 }}</ref>

==Use==
Due to its [[Functionality (chemistry)|functionality]] cyanoacetate reacts:
*At the [[nitrile group]] in various ways:
**Hydrogenation leads to the β-amino acid [[Beta-Alanine|β-alanine]]
**Nucleophilic attack at the carbon, as a step in the synthesis of many heterocycles (see below) and other products
**As a safe cyanide-donor reagent<ref>{{cite journal |title= Ethyl Cyanoacetate: A New Cyanating Agent for the Palladium-Catalyzed Cyanation of Aryl Halides |first1= Shuyan |last1= Zheng |first2= Chunhui |last2= Yu |first3= Zhengwu |last3= Shen |journal= Org. Lett. |year= 2012 |volume= 14 |issue= 14 |pages= 3644–3647 |doi= 10.1021/ol3014914 |pmid= 22783893 }}</ref>
*Nucleophilic attack at the [[ester group]], as part of acyl substitution: reaction with ammonia leads to cyanoacetamide, which can be converted by dehydration with PCl5 or POCl3 to malononitrile.<ref>Mary Eagleson: ''Concise encyclopedia chemistry'', Walter de Gruyter, Berlin - New York 1994, {{ISBN|3-11-011451-8}}.</ref>
*Via the acidic [[methylene group]] as a nucleophile

Ethyl cyanoacetate is a building block for the synthesis of [[Heterocyclic compound|heterocycles]] which are used for example as drugs:
* [[Allopurinol]], used for the treatment of chronic gout, can be synthesized starting with a Knoevenagel condensation with [[triethyl orthoformate]]; the condensation product is cyclized with hydrazine to give a substituted pyrazole and subsequently with formamide to allopurinol, a substituted pyrazolo-pyrimidine.<ref>[[Axel Kleemann]], Jürgen Engel: "Pharmazeutische Wirkstoffe", 2. Aufl., Georg Thieme, Stuttgart - New York 1982, {{ISBN|3-13-558402-X}}.</ref>
* The purine derivatives [[theophylline]], [[caffeine]] and [[uric acid]] are synthetically accessible from ethyl cyanoacetate and [[dimethylurea|''N,N'''-dimethylurea]].<ref>Beyer-Walter: "Lehrbuch der Organischen Chemie", 24. Aufl., S. Hirzel, Stuttgart - Leipzig 2004.</ref>
* The [[pteridine]] derivative [[folic acid]] is assigned to the [[vitamin B complex]]; ethyl cyanoacetate and [[guanidine]] can be used as starting material in a multi-stage [[convergent synthesis]].
* The [[pyrrole]] [[ethosuximide]] is used to treat [[epilepsy]], it can be obtained from ethyl cyanoacetate and [[butanone]] in a multistep synthesis.
* The [[pyrimidine]] derivative [[trimethoprim]] is used as co-trimoxazole in fixed combination with [[sulfamethoxazole]] used as [[bacteriostatic agent]] and is synthesized from ethyl cyanoacetate and [[3,4,5-trimethoxybenzaldehyde]] or its benzyl chloride.
Also many other functional heterocycles are in good yields accessible from ethyl cyanoacetate, such as 3-substituted coumarin derivatives.<ref>{{cite journal |first1= A. A. |last1= Avetisyan |first2= É. V. |last2= Vanyan |first3= M. T. |last3= Dangyan |journal = Chem. Heterocycl. Compounds |title= Synthesis of functionally substituted coumarins |volume= 15 |issue= 9 |pages= 959–960 |year= 1980 |doi= 10.1007/BF00473834 |s2cid= 102024617 }}</ref>

Non-cyclic products from this starting material include:
* The [[anticonvulsant]] [[valproic acid]]
* [[Ethyl cyanoacrylate]], used as superglue, via reaction with [[formaldehyde]]

Ethyl cyanoacetate is also used to prepare 3,3-diphenylpropan-1-amine, which is the precursor used in the synthesis of [[Prenylamine]] & [[Droprenilamine]].

==Safety==
Ethylcyanoacetate has an [[LD50]] of 2820 mg/kg (oral, rat).<ref name=Ullm>Harald Strittmatter, Stefan Hildbrand and Peter Pollak "Malonic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. {{doi| 10.1002/14356007.a16_063.pub2}}</ref>

==References==
{{reflist}}

[[Category:Cyanoacetate esters]]

Category:Cyanoacetate esters

2024-07-30T18:06:00Z

Leiem: added Category:Nitriles using HotCat

[[Category:Nitriles]]

Octocrylene

2024-07-30T18:05:47Z

Leiem: removed Category:Carboxylate esters; added Category:Cyanoacetate esters using HotCat

{{Short description|Organic compound}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402511143
| Name = Octocrylene
| ImageFile = Octocrylene Structural Formula V1.svg
| ImageSize = 220
| ImageAlt = Structural formula of octocrylene
| ImageFile1 = Octocrylene 3D spacefill.png
| ImageSize1 = 220
| ImageAlt1 = Space-filling model of octocrylene
| PIN = 2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
| OtherNames = Octocrylene Octocrilene Uvinul N-539
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21165
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201147
| PubChem = 22571
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5A68WGF6WM
| InChI = 1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
| InChIKey = FMJSMJQBSVNSBF-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FMJSMJQBSVNSBF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6197-30-4
| SMILES = N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
}}
|Section2={{Chembox Properties
| Formula = C24H27NO2
| MolarMass = 361.48 g/mol
| Density = 1.05 g/cm3
| MeltingPtC = 14
| BoilingPtC = 218
| BoilingPt_notes = at 1.5 mmHg
}}
}}

'''Octocrylene''' is an [[organic compound]] used as an ingredient in [[sunscreen]]s and cosmetics. It is an [[ester]] formed by the [[Knoevenagel condensation]] of 2-ethylhexyl cyanoacetate with [[benzophenone]]. It is a viscous, oily liquid that is clear and colorless.

The extended [[Conjugated system|conjugation]] of the [[acrylate]] portion of the molecule absorbs UVB and short-wave UVA ([[ultraviolet]]) rays with wavelengths from 280 to 320 nm,<ref>{{Cite web|url=http://www.smartskincare.com/skinprotection/sunblocks/sunblock_octocylene.html|title=Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent|website=www.smartskincare.com}}</ref> protecting the skin from [[direct DNA damage]]. The ethylhexanol portion is a [[fatty alcohol]], adding [[emollient]] and oil-like (water resistant) properties.

==Safety==
Octocrylene can penetrate into the skin where it acts as a [[photosensitizer]], resulting in an increased production of free radicals under illumination.<ref name="Hanson">{{cite journal |author1=Hanson Kerry M. |author2=Gratton Enrico |author3=Bardeen Christopher J. |title=Sunscreen enhancement of UV-induced reactive oxygen species in the skin |doi=10.1016/j.freeradbiomed.2006.06.011| journal=Free Radical Biology and Medicine |volume=41 |issue=8 |pages=1205–1212 |year=2006 |pmid=17015167 |s2cid=13999532 |url=http://www.escholarship.org/uc/item/9f14s2dd }}</ref> It may also pass through the skin, into the blood stream, eventually being metabolized and excreted in urine in form of its metabolites.<ref>{{cite journal |last1=Bury |first1=Daniel |last2=Belov |first2=Vladimir N. |last3=Qi |first3=Yulin |last4=Hayen |first4=Heiko |last5=Volmer |first5=Dietrich A. |last6=Brüning |first6=Thomas |last7=Koch |first7=Holger M. |title=Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS |journal=Analytical Chemistry |date=2018 |volume=90 |issue=1 |pages=944–951 |doi=10.1021/acs.analchem.7b03996|pmid=29188988 |hdl=21.11116/0000-0000-3212-3 |hdl-access=free }}</ref><ref>{{cite journal |last1=Bury |first1=Daniel |last2=Modick-Biermann |first2=Hendrik |last3=Leibold |first3=Edgar |last4=Brüning |first4=Thomas |last5=Koch |first5=Holger M. |title=Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure |journal=Archives of Toxicology |date=2019 |volume=93 |issue=5 |pages=1227–1238 |doi=10.1007/s00204-019-02408-7|pmid=30739143 |s2cid=59622082 }}</ref> Octocrylene can convert to [[benzophenone]] through a retro-[[aldol condensation]].<ref>{{cite journal |last1=Downs |first1=C. A. |last2=DiNardo |first2=Joseph C. |last3=Stien |first3=Didier |last4=Rodrigues |first4=Alice M. S. |last5=Lebaron |first5=Philippe |title=Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products |journal=Chemical Research in Toxicology |date=7 March 2021 |volume=34 |issue=4 |pages=1046–1054 |doi=10.1021/acs.chemrestox.0c00461|pmid=33682414 |doi-access=free }}</ref> The reaction occurs slowly over time, yielding significant concentration of benzophenone in all commercial cosmetics tested formulated with octocrylene.

In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and trigger mitochondrial dysfunction.<ref>{{cite journal |last1=Stien |first1=Didier |last2=Clergeaud |first2=Fanny |last3=Rodrigues |first3=Alice M.S. |last4=Lebaron |first4=Karine |last5=Pillot |first5=Rémi |last6=Romans |first6=Pascal |last7=Fagervold |first7=Sonja |last8=Lebaron |first8=Philippe |title=Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction |journal=Analytical Chemistry |date=2019 |volume=91 |issue=1 |pages=990–995 |doi=10.1021/acs.analchem.8b04187|pmid=30516955 |s2cid=54567139 |url=https://hal.sorbonne-universite.fr/hal-01973836/file/Manuscript%20File.pdf }}</ref>

===Regulation===
[[Palau]] has banned the sale and use of three reef-toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018.<ref>{{cite web |last1=Republic of Palau |title=RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw |url=https://www.palaugov.pw/documents/rppl-no-10-30-the-responsible-tourism-education-act-of-2018/ |website=PalauGov.pw Your guide to finding and using Palau National Government services |access-date=16 October 2019}}</ref> The [[United States Virgin Islands]] has also banned the use of sunscreens containing octocrylene, requiring that all visitors use "non-nano mineral sunscreen" containing zinc oxide and titanium dioxide.<ref>{{cite web |title=Sustainable Travel in USVI |url=https://www.visitusvi.com/travel-information/sustainable |website=United States Virgin Islands |access-date=17 February 2024 |archive-url=https://web.archive.org/web/20240114080831/https://www.visitusvi.com/travel-information/sustainable |archive-date=14 January 2024 |language=en |quote=Avoid sunscreens that contain the “Toxic 3 Os” of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States Virgin Islands. Wear rashguards, hats and use only non-nano mineral sunscreen containing zinc oxide and titanium dioxide, the only sunscreen ingredients deemed safe and effective by the FDA.}}</ref>

==See also==

*[[Sunscreen controversy]]

==References==
{{reflist}}

{{Sunscreening agents}}

[[Category:Cyanoacetate esters]]
[[Category:Household chemicals]]
[[Category:Sunscreening agents]]
[[Category:2-Ethylhexyl esters]]

3,4,8-Trimethoxyphenanthrene-2,5-diol

2024-07-29T03:00:17Z

Leiem: CASRN

{{Chembox
| ImageFile = 3,4,8-trimethoxyphenanthrene-2,5-diol.svg
| ImageAlt = Chemical structure of 3,4,8-trimethoxyphenanthrene-2,5-diol
| PIN = 3,4,8-Trimethoxyphenanthrene-2,5-diol
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 1239257-99-8
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEMBL = 1085553
| PubChem = 46871897
| SMILES = COc3c(OC)c1c2c(O)ccc(OC)c2ccc1cc3O
| StdInChI=1S/C17H16O5/c1-20-13-7-6-11(18)15-10(13)5-4-9-8-12(19)16(21-2)17(22-3)14(9)15/h4-8,18-19H,1-3H3
| StdInChIKey = RWWKZMYUOWSSPW-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=17 | H=16 | O=5
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''3,4,8-Trimethoxyphenanthrene-2,5-diol''' is one of the 17 [[phenanthrenes]] found in the extract of the stems of the orchid ''[[Dendrobium nobile]]''.<ref>Hwang JS, Lee SA, Hong SS, Han XH, Lee C, Kang SJ, Lee D, Kim Y, Hong JT, Lee MK, Hwang BY,."Phenanthrenes from Dendrobium nobile and their inhibition of the LPS-induced production of nitric oxide in macrophage RAW 264.7 cells. ''Bioorg Med Chem Lett''. 2010 Jun 15;20(12):3785-7, {{doi|10.1016/j.bmcl.2010.04.054}}</ref>

== References ==
{{Reflist}}



{{Phenanthrenes}}

{{DEFAULTSORT:Trimethoxyphenanthrene-2,5-diol, 3,4,8-}}
[[Category:Phenanthrenoids]]
[[Category:Methoxy compounds]]

{{aromatic-stub}}

Tetrakis(acetonitrile)copper(I) tetrafluoroborate

2024-07-27T07:02:48Z

Leiem: added Category:Tetrafluoroborates using HotCat

{{Chembox

| ImageFile = Tetrakis_acetonitril_copper_tetrafluoroborate.svg
| ImageSize = 200px
| ImageAlt =

| IUPACName =
| OtherNames =

| Section1 = {{Chembox Identifiers
| CASNo = 15418-29-8
| PubChem = 10990673
| SMILES =
}}
| Section2 = {{Chembox Properties
| Formula = C8H12BCuF4N4
| MolarMass = 314.56 g·[[mol]]−1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Tetrakis(acetonitrile)copper(I) tetrafluoroborate''' is a [[complex compound]] of [[copper]] with [[acetonitrile]] as the ligand and [[tetrafluoroborate]] as the counterion.

== Preparation ==
Tetrakis(acetonitrile)copper(I) tetrafluoroborate can be prepared starting from [[nitrosyl tetrafluoroborate]], which is obtained from [[dinitrogen tetroxide]] and [[tetrafluoroboric acid]]. The nitrosyl salt is then reacted with metallic [[copper]] in [[acetonitrile]], initially producing a green-blue copper(II) complex. This complex is reduced to the copper(I) complex by further reaction with metallic copper. By boiling with additional copper powder until decolorization, the copper(I) complex is obtained.<ref>{{citation|author=B. J. Hathaway, D. G. Holah, J. D. Postlethwaite |date=1961 |doi=10.1039/jr9610003215 |pages=3215 |periodical=Journal of the Chemical Society (Resumed) |title=630. The preparation and properties of some tetrakis(methylcyanide)copper(I) complexes}}</ref>

== Properties ==
Tetrakis(acetonitrile)copper(I) tetrafluoroborate forms colorless crystals in the orthorhombic crystal system in the space group Pna21 with the [[lattice parameters]] ''a'' = 23.882 Å; ''b'' = 8.3285 Å; ''c'' = 20.338 Å, and twelve [[unit cell]]s. The compound is isomorphous with [[tetrakis(acetonitrile)copper(I) perchlorate]] and [[tetrakis(acetonitrile)silver(I) perchlorate]].<ref>{{citation|author=P. G. Jones, O. Crespo |date=1998-01-15 |doi=10.1107/S0108270197013322 |issue=1 |pages=18–20 |periodical=Acta Crystallographica Section C Crystal Structure Communications |title=Tetrakis(acetonitrile- N )copper(I) Tetrafluoroborate |volume=54}}</ref>

== Use ==
Tetrakis(acetonitrile)copper(I) tetrafluoroborate can be reacted with [[methoxyisobutyl isonitrile]] to produce [[tetrakis(methoxyisobutyl isonitrile)copper(I) tetrafluoroborate|Tetrakis(methoxyisobutyl isonitrile)copper(I) tetrafluoroborate]].<ref>{{citation|author=Te-Wei Lee, Chang-Shinn Su, Gann Ting |date=February 1996 |doi=10.1016/0969-8043(95)00249-9 |issue=2 |pages=207–210 |periodical=Applied Radiation and Isotopes |title=Synthesis, reactivity and 99mTc labelling of 2-alkoxyisobutylisonitrile |volume=47}}</ref> This compound is used to produce [[Technetium (99mTc) sestamibi|technetium(99mTc)-sestamibi]].<ref>{{citation|author=M. E. Wilson, J. C. Hung, R. J. Gibbons |date=July 1993 |doi=10.1097/00006231-199307000-00005 |issue=1 |pages=544–549 |periodical=Nuclear Medicine Communications |title=An alternative method for rapid preparation of 99Tcm-sestamibi: |volume=14}}</ref>

== See also ==
* [[Tetrakis(acetonitrile)copper(I) hexafluorophosphate]]

==References==
{{reflist}}

[[Category:Copper complexes]]
[[Category:Tetrafluoroborates]]