Cyanoform

Cyanoform

Names
IUPAC name Methanetricarbonitrile
Other names Tricyanomethane
Identifiers
ChemSpider	4402366
InChI InChI=1S/C4HN3/c5-1-4(2-6)3-7/h4H Key: HFWIMJHBCIGYFH-UHFFFAOYSA-N InChI=1/C4HN3/c5-1-4(2-6)3-7/h4H Key: HFWIMJHBCIGYFH-UHFFFAOYAU
Jmol-3D images	Image
PubChem	5232958
SMILES C(#N)C(C#N)C#N
Properties
Molecular formula	C4HN3
Molar mass	91.07 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cyanoform (tricyanomethane) is a cyanocarbon and derivative of methane with three cyano groups. It has thus far not been isolated as free acid. Dilute solutions of this acid have been prepared, however, and its salts are well known. Cyanoform ranks as one of the most acidic of the carbon acids with an estimated pK_a of -5.1 in water and measured pK_a 5.1 in acetonitrile.^[1] The reaction of sulfuric acid with sodium tricyanomethanide in water (a reaction first tried by H. Schmidtmann in 1896 with inconclusive results^[2]) is reported to result in the formation of the hydrate (NC)₃C⁻H₃O⁺ or the formation of (Z)-3- amino-2-cyano-3-hydroxyacrylamide (H₂N)(OH)C=C(CN)CONH₂ depending on the precise conditions.^[3] The reaction of HCl gas with sodium tricyanomethanide dissolved in THF is reported to yield 1-chloro-1-amino-2,2-dicyanoethylene ((NC)₂C=C(NH₂)Cl) and its tautomer.

References