Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Dinitrogen difluoride: Difference between pages
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Saving copy of the {{chembox}} taken from revid 476955332 of page Dinitrogen_difluoride for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Dinitrogen_difluoride|oldid=476955332}} 476955332] of page [[Dinitrogen_difluoride]] with values updated to verified values.}} |
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{{chembox |
{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 438057472 |
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| Watchedfields = changed |
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| Name = ''cis''-Dinitrogen difluoride <small>(left)</small> and ''trans''-Dinitrogen difluoride <small>(right)</small> |
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| verifiedrevid = 476992203 |
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| ImageFile=Cistrans-Distickstoffdifluorid.png |
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| ImageFileL1 = (Z)-Dinitrogen-difluoride.png |
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| ImageSize=200px |
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| ImageCaptionL1 = ''cis''-dinitrogen difluoride |
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| ImageFileR1 = (E)-Dinitrogen-difluoride.png |
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| ImageCaptionR1 = ''trans''-dinitrogen difluoride |
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| ImageFileL2 = (Z)-Dinitrogen-difluoride-3D-balls.png |
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| ImageAltL2 = ''cis''-dinitrogen difluoride ball-and-stick model |
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| ImageFileR2 = (E)-Dinitrogen-difluoride-3D-balls.png |
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| ImageAltR2 = ''trans''-dinitrogen difluoride ball-and-stick model |
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| Reference = <ref name="hand"> |
| Reference = <ref name="hand"> |
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{{cite book |
{{cite book | last = Lide | first = David R. | year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| edition = 87th | volume = |
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| location = Boca Raton, FL |
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| publisher = CRC Press |
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| isbn = 0-8493-0594-2 | pages = 4–73, 5–15, 9–46}}</ref> |
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| IUPACName = ''cis''- or ''trans''-dinitrogen difluoride |
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| OtherNames = ''cis''- or ''trans''-difluorodiazene |
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|Section1={{Chembox Identifiers<!-- cis; index=1 --> |
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| ChemSpiderID1 = 10326121 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4516471 |
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| ChemSpiderID1_Comment = (''cis'') |
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| InChI = 1/F2N2/c1-3-4-2/b4-3+ |
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| ChemSpiderID2 = 4516471 |
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| InChIKey = DUQAODNTUBJRGF-ONEGZZNKBY |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2_Comment = (''trans'') |
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| InChI1 = 1S/F2N2/c1-3-4-2/b4-3- |
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| InChIKey1 = DUQAODNTUBJRGF-ONEGZZNKBY |
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| InChI1_Comment = (''cis'') |
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| SMILES1 = F\N=N\F |
| SMILES1 = F\N=N\F |
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| SMILES1_Comment = (''cis'') |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES2 = F\N=N/F |
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| StdInChI = 1S/F2N2/c1-3-4-2/b4-3+ |
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| SMILES2_Comment = (''trans'') |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI3_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DUQAODNTUBJRGF-ONEGZZNKSA-N |
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| InChI3 = 1S/F2N2/c1-3-4-2/b4-3+ |
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| CASNo_Ref = {{cascite|correct|??}} |
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| InChIKey3_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = <!-- blanked - oldvalue: 13812-43-6 --> |
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| InChIKey3 = DUQAODNTUBJRGF-ARJAWSKDSA-N |
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| CASOther= (''cis'') <br />[13776-62-0] (''trans'') |
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| InChI2 = 1/F2N2/c1-3-4-2/b4-3+ |
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| SMILES = ''cis'': F/N=N\F <br />''trans'': F\N=N\F |
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| InChIKey2 = DUQAODNTUBJRGF-ONEGZZNKBY |
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| InChI2_Comment = (''trans'') |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| CASNo1 = 13812-43-6 |
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| CASNo1_Comment = (''cis'') |
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| CASNo2 = 13776-62-0 |
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| CASNo2_Comment = (''trans'') |
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| PubChem1 = 5364290 |
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| PubChem1_Comment = (''cis'') |
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| PubChem2 = 5462838 |
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| PubChem2_Comment = (''trans'') |
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}} |
}} |
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|Section3={{Chembox Properties |
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| Appearance = |
| Appearance = Colorless gas |
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| |
| Formula = FN=NF |
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| N=2|F=2 |
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| MolarMass = 66.010 g/mol |
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| Density = 2.698 g/L |
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| MeltingPt = ''cis'': less than |
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| MeltingPtC = −195 |
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| BoilingPt = ''cis'': -105.75 °C<br />''trans'': -111.45 °C |
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| MeltingPt_notes = <br/>''trans'': {{cvt|−172|C|F}} |
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| BoilingPt = ''cis'': |
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| BoilingPtC = −105.75 |
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| BoilingPt_notes = <br/>''trans'': {{cvt|−111.45|C|F}} |
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| Dipole = ''cis'': 0.16 [[Debye|D]]<br />''trans'': 0 D |
| Dipole = ''cis'': 0.16 [[Debye|D]]<br />''trans'': 0 D |
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}} |
}} |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = ''cis'': 69.5 kJ/mol<br |
| DeltaHf = ''cis'': 69.5 kJ/mol<br/>''trans'': 82.0 kJ/mol |
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| DeltaHc = |
| DeltaHc = |
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| Entropy = |
| Entropy = |
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| HeatCapacity = }} |
| HeatCapacity = |
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}} |
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|Section9={{Chembox Related |
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| OtherAnions = [[Azide]] |
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| OtherCations = {{ubl|[[Ammonium]]|[[Diazonium compounds]]|[[Pentazenium]]|[[Tetrafluoroammonium]]}} |
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| OtherFunction_label = Binary fluoro-[[azane]]s |
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| OtherFunction = |
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| OtherCompounds = {{ubl|[[Azo compound]]s|[[Diazene]]|[[Triazene]]|[[Tetrazene]]|[[Nitrogen trifluoride]]|[[Tetrafluorohydrazine]]}} |
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}} |
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}} |
}} |
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'''Dinitrogen difluoride''' is a [[chemical compound]] with the formula {{chem2|N2F2}}. It is a gas at room temperature, and was first identified in 1952 as the [[thermal decomposition]] product of the [[fluorine azide]] ({{chem2|FN3}}). It has the structure {{chem2|F\sN\dN\sF}} and exists in both [[cis–trans isomerism|''cis'' and ''trans'' isomers]], as typical for [[diimide]]s. |
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== Isomers == |
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The ''cis'' isomer has C<sub>2v</sub> symmetry and the ''trans'' isomer has C<sub>2h</sub> symmetry. These isomers can interconvert, but the process is slow enough at low temperature that the two can separated by low-temperature [[fractionation]].{{clarify|issue=What type of fractionation (distillation, crystallization, etc.)?|date=January 2024}} The ''trans'' isomer is less [[thermodynamic stability|thermodynamically stable]]<ref>{{Cite journal |last1=Christe |first1=Karl O. |last2=Dixon |first2=David A. |last3=Grant |first3=Daniel J. |last4=Haiges |first4=Ralf |last5=Tham |first5=Fook S. |last6=Vij |first6=Ashwani |last7=Vij |first7=Vandana |last8=Wang |first8=Tsang-Hsiu |last9=Wilson |first9=William W. |date=2010-08-02 |title=Dinitrogen Difluoride Chemistry. Improved Syntheses of cis - and trans -N 2 F 2 , Synthesis and Characterization of N 2 F + Sn 2 F 9 − , Ordered Crystal Structure of N 2 F + Sb 2 F 11 − , High-Level Electronic Structure Calculations of cis -N 2 F 2 , trans -N 2 F 2 , F 2 N═N, and N 2 F + , and Mechanism of the trans−cis Isomerization of N 2 F 2 |url=https://pubs.acs.org/doi/10.1021/ic100471s |journal=Inorganic Chemistry |language=en |volume=49 |issue=15 |pages=6823–6833 |doi=10.1021/ic100471s |pmid=20465274 |issn=0020-1669}}</ref> but can be stored in glass vessels. The ''cis'' isomer attacks glass over a time scale of about 2 weeks to form [[silicon tetrafluoride]] and [[nitrous oxide]]:<ref>{{Greenwood&Earnshaw2nd}}</ref>{{page needed|date=January 2024}} |
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:{{chem2|2 N2F2 + SiO2 → SiF4 + 2 N2O}} |
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== Preparation == |
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Most preparations of dinitrogen difluoride give mixtures of the two isomers, but they can be prepared independently. |
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An aqueous method involves ''N'',''N''-difluoro[[urea]] with concentrated [[potassium hydroxide]]. This gives a 40% yield with three times more of the trans isomer.<ref name="Sykes1989">{{cite book|last=Sykes|first=A. G.|title=Advances in Inorganic Chemistry|url=https://books.google.com/books?id=qzN5pnPwuaoC&pg=PA171|accessdate=21 June 2014|date=1989-07-17|publisher=Academic Press|isbn=9780080578828|page=171}}</ref> |
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[[Difluoramine]] forms a solid unstable compound with [[potassium fluoride]] (or [[rubidium fluoride]] or [[caesium fluoride]]) which decomposes to dinitrogen difluoride.<ref name="Sykes1989"/> |
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It can also be prepared by [[photolysis]] of [[tetrafluorohydrazine]] and [[bromine]]:<ref name="IS14">{{citation|surname1=Leon M. Zaborowski|display-authors=et al|editor-surname1= Aaron Wold and John K. Ruff|series=Inorganic Syntheses|title=Chlorodifluoroamine and Difluorodiazene - B. Difluorodiazene (Dinitrogen difluoride)|volume=14|publisher=McGraw-Hill Book Company, Inc.|pages=34–39|date=1973|language=German |
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}}</ref> |
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:{{chem2|N2F4}} {{overunderset|→|''hv''|{{chem2|Br2}}}} {{chem2|N2F2 + byproducts}} |
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== Reactions == |
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The ''cis'' form of difluorodiazene will react with strong fluoride ion acceptors such as [[antimony pentafluoride]] to form the [[Linear molecular geometry|linear]]<ref name=pubs></ref> {{chem2|[N\tN\sF]+}} cation (fluorodiazonium cation<ref name=pubs>{{cite journal | url=https://pubs.acs.org/doi/10.1021/ic00110a007 | doi=10.1021/ic00110a007 | title=Gaseous Fluorodiazonium Ions. Experimental and Theoretical Study on Formation and Structure of FN2+ | year=1995 | last1=Cacace | first1=Fulvio | last2=Grandinetti | first2=Felice | last3=Pepi | first3=Federico | journal=Inorganic Chemistry | volume=34 | issue=6 | pages=1325–1332 }}</ref>) which forms a [[Salt (chemistry)|salt]] with the formula {{chem2|[N\tN\sF]+[SbF6]−}} (fluorodiazonium hexafluoroantimonate(V)). |
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:{{chem2|F\sN\dN\sF + SbF5 → [N\tN\sF]+[SbF6]−}} |
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Analogous reaction of ''cis''-difluorodiazene with [[arsenic pentafluoride]] gives white solid salt with the formula {{chem2|[N\tN\sF]+[AsF6]−}}<ref name=pubs></ref> (fluorodiazonium hexafluoroarsenate(V)). |
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:{{chem2|F\sN\dN\sF + AsF5 → [N\tN\sF]+[AsF6]−}} |
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In the solid phase, the observed {{chem2|N\tN}} and {{chem2|N\sF}} bond distances in the {{chem2|[N\tN\sF]+}} cation are 1.089(9) and 1.257(8) Å respectively, among the shortest experimentally observed N-N and N-F bonds. |
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== References == |
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{{reflist}}{{Nitrogen compounds}} |
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[[Category:Inorganic nitrogen compounds]] |
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[[Category:Nitrogen fluorides]] |
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[[Category:Nonmetal halides]] |