Tetracyanomethane

Tetracyanomethane
Names
Preferred IUPAC name
Methanetetracarbonitrile
Other names
carbon tetracyanide; 2,2-dicyanomalononitrile
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C5N4/c6-1-5(2-7,3-8)4-9
    Key: XKGUKYPCHPHAJL-UHFFFAOYSA-N
  • C(#N)C(C#N)(C#N)C#N
Properties
C(CN)4
Molar mass 116.083 g·mol−1
Appearance white crystals
Structure
trigonal
R3c
a = 9.062, c = 11.625
137.8 Å3
6
tetrahedron
Thermochemistry[1]
−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]

  1. ^ Barnes, D.S.; Mortimer, C.T.; Mayer, E. (July 1973). "The enthalpy of formation of tetracyanomethane". The Journal of Chemical Thermodynamics. 5 (4): 481–483. doi:10.1016/S0021-9614(73)80095-3.
  2. ^ Mayer, Erwin (1969). "Darstellung und Eigenschaften von Tetracyanmethan". Monatshefte für Chemie. 100 (2): 462–468. doi:10.1007/BF00904089. S2CID 92450428.
  3. ^ Britton, D. (1 July 1974). "The crystal structure of tetracyanomethane, C(CN)4". Acta Crystallographica Section B. 30 (7): 1818–1821. Bibcode:1974AcCrB..30.1818B. doi:10.1107/S0567740874005863.