Melem
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| Names | |
|---|---|
| IUPAC name
11-imino-2,4,6,8,10,12,13-heptazatricyclo[7.3.1.05,13]trideca-1(12),2,4,7,9-pentaene-3,7-diamine
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| Other names
2,5,8-triamino-heptazine; 2,5,8-triamino-tri-s-triazine; cyamelurotriamide; triamino-s-heptazine; 1,3,4,6,7,9,9b-Heptaazaphenalene-2,5,8-triamine
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| Identifiers | |
3D model (JSmol)
|
|
| 27284 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.014.657 |
| EC Number |
|
| 241276 | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C6H6N10 | |
| Molar mass | 218.18 g/mol |
| Appearance | white solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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In chemistry, melem is a compound with formula C
6N
10H
6; specifically, 2,5,8-triamino-heptazine or 2,5,8-triamino-tri-s-triazine, whose molecule can be described as that of heptazine with the three hydrogen atoms replaced by amino groups. It is a white crystalline solid.[1]
Preparation
Melem can be prepared by thermal decomposition of various C−N−H compounds, such as melamine C3N3(NH2)3, dicyandiamide H4C2N4, ammonium dicyanamide NH4[N(CN)2], cyanamide H2CN2, at 400 to 450 °C.[1][2]
Structure and properties
Crystal structure
Melem crystallizes in the group P21/c (No. 14), with parameters a = 739.92(1) pm, b = 865.28(3) pm, c = 1338.16(4) pm, β = 99.912(2)°, and Z = 4. The almost-planar molecules are arranged in parallel layers spaced 327 pm apart. The molecule is in the triamino form, rather than one of the possible tautomers.[1]
Thermal decomposition
When heated above 560°, melem transforms into a graphite-like C−N material.[1]
Melemium cations
Melem accepts up to three protons yielding cations called melemium [(NH2)3(C6N7Hx)]x+. Some salts described in the literature are melemium sulfate, [(NH
2)
3(C
6N
7H
2)]SO
4 • 2H
2O, melemium perchlorate, [(NH
2)
3(C
6N
7H)]ClO
4 • H
2O, melemium hydrogensulfate [(NH
2)
3(C
6N
7H
3)](HSO
4)
3 and two melemium methylsulfonates [(NH
2)
3(C
6N
7H
2)](SO
3CH
3)
2 • H
2O and [(NH
2)
3(C
6N
7H)][(NH
2)
3(C
6N
7H
2)](SO
3CH
3)
3 • H
2O. The protons can be inserted in any of the six outer nitrogen atoms of the heptazine core, yielding many tautomers of apparently similar energies.[3]
See also
- Triazine H
3C
3N
3, with a single C-N ring - Melamine (NH
2)
3(C
3N
3), triamino triazine - Melaminium [H(NH
2)
3(C
3N
3)]+
, a cation derived from melamine - Melam ((NH
2)
2(C
3N
3))
2NH, a condensation dimer of melamine - Melamium [H((NH
2)
2(C
3N
3))
2NH]+
, a cation derived from melam - Melon (NH
2)(NH(C
6N
7H)NH)
nH, a condensation oligomer of melem
References
- ^ a b c d Barbara Jürgens, Elisabeth Irran, Jürgen Senker, Peter Kroll, Helen Müller, Wolfgang Schnick (2003): "Melem (2,5,8-Triamino-tri-s-triazine), an Important Intermediate during Condensation of Melamine Rings to Graphitic Carbon Nitride: Synthesis, Structure Determination by X-ray Powder Diffractometry, Solid-State NMR, and Theoretical Studies". Journal of the American Chemical Society, volume 125, issue 34, pages 10288-10300. doi:10.1021/ja0357689
- ^ Tamikuni Komatsu (2001)> "The First Synthesis and Characterization of Cyameluric High Polymers". Macromolecular Chemistry and Physics, volume 202, issue 1, pages 19-25. doi:10.1002/1521-3935(20010101)202:1<19::AID-MACP19>3.0.CO;2-G
- ^ Fabian Karl Keßler (2019), Structure and Reactivity of s-Triazine-Based Compounds in C/N/H Chemistry. Doctoral thesis, Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München
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