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Names | |
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Preferred IUPAC name Methanetetracarbonitrile | |
Other names carbon tetracyanide; 2,2-dicyanomalononitrile | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C(CN)4 | |
Molar mass | 116.083 g·mol−1 |
Appearance | white crystals |
Structure | |
trigonal | |
R3c | |
a = 9.062, c = 11.625 | |
Lattice volume (V) | 137.8 Å3 |
Formula units (Z) | 6 |
tetrahedron | |
Thermochemistry [1] | |
Std enthalpy of formation (ΔfH⦵298) | −146.2 kcal/mol |
−616.4 kcal/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tetracyanomethane or carbon tetracyanide is an organic compound with the chemical formula C(CN)4. It is a percyanoalkane. It is a molecular carbon nitride. The structure can be considered as methane with all hydrogen atoms replaced by cyanide groups. It was first made by Erwin Mayer in 1969. [2] [3]
Tetracyanomethane is a solid at room temperature. It decomposes over 160 °C without melting, and although it can be in a dilute vapour, no liquid form is known. [2] The molecules of tetracyanomethane have a tetrahedral symmetry (43m or Td). The molecule has C-C distance of 1.484 Å and C-N distance of 1.161 Å in the gas form. In the solid the C≡N bond shortens to 1.147 Å. [3] The C-C bond has a force constant of 4.86×105 dyn/cm which is slightly greater than the C-Cl bond in carbon tetrachloride, but a fair bit weaker than in the tricyanomethanide ion. [4] At pressures over 7 GPa tetracyanomethane starts to polymerize to form a disorganised covalent network solid. At higher pressure the white colour [1] yellows and darkens to black. Over 20 GPa the polymerization is total. [5]
The bulk modulus K0 = 4.4 and its derivative K0' = 18. [5]
Tetracyanomethane can be made by reacting cyanogen chloride with silver tricyanomethanide. [4]
In an acid solution in water tetracyanomethane is hydrolysed to yield tricyanomethanide and ammonium ions along with carbon dioxide. In alkaline solutions tricyanomethanide and cyanate ions are produced. [4]