Melem
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
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
Identifiers
3D model (JSmol)
27284
ChEBI
ChemSpider
ECHA InfoCard 100.014.657
EC Number
  • 216-122-4
241276
UNII
  • InChI=1S/C6H6N10/c7-1-10-4-12-2(8)14-6-15-3(9)13-5(11-1)16(4)6/h(H6,7,8,9,10,11,12,13,14,15) ☒N
    Key: YSRVJVDFHZYRPA-UHFFFAOYSA-N
  • C1(=NC2=NC(=N)N=C3N2C(=NC(=N3)N)N1)N
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).
Infobox references

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
    3    C
    3    N
    3    , with a single C-N ring
  • Melamine (NH
    2    )
    3    (C
    3    N
    3    )    , triamino triazine
  • Melaminium [H(NH
    2    )
    3    (C
    3    N
    3    )]+
    , a cation derived from melamine
  • Melam ((NH
    2    )
    2    (C
    3    N
    3    ))
    2    NH    , a condensation dimer of melamine
  • Melamium [H((NH
    2    )
    2    (C
    3    N
    3    ))
    2    NH]+
    , a cation derived from melam
  • Melon (NH
    2    )(NH(C
    6    N
    7    H)NH)
    n    H    , a condensation oligomer of melem

References

  1. 1 2 3 4 Jürgens, Barbara; Irran, Elisabeth; Senker, Jürgen; Kroll, Peter; Müller, Helen; Schnick, Wolfgang (2003-08-01). "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. 125 (34): 10288–10300. doi:10.1021/ja0357689. ISSN 0002-7863.
  2. ↑ Tamikuni Komatsu (2001)> Komatsu, Tamikuni (2001-01-01). "The First Synthesis and Characterization of Cyameluric High Polymers". Macromolecular Chemistry and Physics. 202 (1): 19–25. doi:10.1002/1521-3935(20010101)202:1<19::AID-MACP19>3.0.CO;2-G. ISSN 1022-1352.
  3. ↑ 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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