Melem
title: "Melem" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["heterocyclic-compounds-with-3-rings", "nitrogen-heterocycles", "tricyclic-compounds", "amines"] topic_path: "general/heterocyclic-compounds-with-3-rings" source: "https://en.wikipedia.org/wiki/Melem" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| Name = Melem | ImageFile = File:Melem Structural Formulae.svg | ImageClass = skin-invert | IUPACName = 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 | OtherNames = 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 |Section1={{Chembox Identifiers | Abbreviations = | CASNo_Ref = | CASNo = 1502-47-2 | UNII_Ref = | UNII = WP6U3U42XL | EINECS = 216-122-4 | PubChem = 73919 | ChemSpiderID_Ref = | ChemSpiderID = 4575652 | SMILES = C1(=NC2=NC(=N)N=C3N2C(=NC(=N3)N)N1)N | StdInChI = 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) | StdInChIKey = YSRVJVDFHZYRPA-UHFFFAOYSA-N | StdInChI_Ref = | MeSHName = | ChEBI_Ref = | ChEBI = 38055 | KEGG_Ref = | KEGG = | Gmelin = 241276 | Beilstein = 27284 |Section2={{Chembox Properties | Formula = C6H6N10 | MolarMass = 218.18 g/mol | Appearance = white solid | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} In chemistry, melem is a compound with formula ; 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.
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.
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.
Thermal decomposition
When heated above 560°, melem transforms into a graphite-like C−N material.
Melemium cations
Melem accepts up to three protons yielding cations called melemium . Some salts described in the literature are melemium sulfate, • 2, melemium perchlorate, • , melemium hydrogensulfate and two melemium methylsulfonates • and • . The protons can be inserted in any of the six outer nitrogen atoms of the heptazine core, yielding many tautomers of apparently similar energies.
References
References
- Jürgens, Barbara. (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.
- Komatsu, Tamikuni. (2001-01-01). "The First Synthesis and Characterization of Cyameluric High Polymers". Macromolecular Chemistry and Physics.
- Fabian Karl Keßler (2019), ''[https://edoc.ub.uni-muenchen.de/25071/1/Kessler_Fabian_K.pdf 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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