Tetracyanomethane

Tetracyanomethane
Names
	Preferred IUPAC name Methanetetracarbonitrile
	Other names carbon tetracyanide; 2,2-dicyanomalononitrile
Identifiers
CAS Number	24331-09-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	124462;
PubChem CID	141101;
UNII	K559RM8NV6 ;
CompTox Dashboard (EPA)	DTXSID70179070 ;
	InChI InChI=1S/C5N4/c6-1-5(2-7,3-8)4-9 Key: XKGUKYPCHPHAJL-UHFFFAOYSA-N;
	SMILES C(#N)C(C#N)(C#N)C#N;
Properties
Chemical formula	C(CN)4
Molar mass	116.083 g·mol−1
Appearance	white crystals
Structure
Crystal structure	trigonal
Space group	R3c
Lattice constant	a = 9.062, c = 11.625
Lattice volume (V)	137.8 Å3
Formula units (Z)	6
Molecular shape	tetrahedron
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−146.2 kcal/mol
Heat of combustion, higher value (HHV)	−616.4 kcal/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

^ 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.
^ Mayer, Erwin (1969). "Darstellung und Eigenschaften von Tetracyanmethan". Monatshefte für Chemie. 100 (2): 462–468. doi:10.1007/BF00904089. S2CID 92450428.
^ 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.