Cyanoform

Cyanoform
Names
	IUPAC name Methanetricarbonitrile
	Other names Tricyanomethane
Identifiers
CAS Number	454-50-2;
3D model (JSmol)	Interactive image;
ChemSpider	4402366;
PubChem CID	5232958;
CompTox Dashboard (EPA)	DTXSID20411917 ;
	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;
	SMILES C(#N)C(C#N)C#N;
Properties
Chemical formula	C4HN3
Molar mass	91.073 g·mol−1
	Except where otherwise noted, data are 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. For many years, chemists have been unable to isolate this compound as a neat, free acid. However, in September 2015, reports surfaced of a successful isolation.^[1]

Properties

Dilute solutions of this acid, as well as its salts, have long been 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 of 5.1 in acetonitrile.^[2] The reaction of sulfuric acid with sodium tricyanomethanide in water (a reaction first tried by H. Schmidtmann in 1896 with inconclusive results^[3]) 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.^[4] 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.

Isolation

In September 2015 cyanoform was successfully isolated by a team of scientists at Ludwig Maximilian University of Munich. The team discovered that cyanoform was stable at temperatures below –40° Celsius; previous beliefs were that cyanoform was stable at room temperature. The isolation confirmed that cyanoform is a colorless liquid.^[5]

References

^ Soltner, T.; Häusler J.; Kornath A.J. "The Existence of Tricyanomethane" Angewandte Chemie International Edition 2015. doi:10.1002/anie.201506753
^ Raamat, E.; Kaupmees, K.; Ovsjannikov, G.; Trummal, A.; Kütt, A.; Saame, J.; Koppel, I.; Kaljurand, I.; Lipping, L.; Rodima, T.; Pihl, V.; Koppel, I. A.; Leito, I. (2013). "Acidities of strong neutral Brønsted acids in different media". J. Phys. Org. Chem. 26 (2): 162–170. doi:10.1002/poc.2946.
^ Schmidtmann, H. (1896). "Ueber einige Derivate des Malonitrils" (PDF). Berichte der deutschen chemischen Gesellschaft. 29 (2): 1168–1175. doi:10.1002/cber.18960290204.
^ Šišak, Dubravka; McCusker, Lynne B.; Buckl, Andrea; Wuitschik, Georg; Wu, Yi-Lin; Schweizer, W. Bernd; Dunitz, Jack D. (2010). "The Search for Tricyanomethane (Cyanoform)". Chemistry: A European Journal. 16 (24): 7224–30. doi:10.1002/chem.201000559. PMID 20480465.
^ Mole, B - Elusive acid finally created https://www.sciencenews.org/article/elusive-acid-finally-created

[1] Soltner, T.; Häusler J.; Kornath A.J. "The Existence of Tricyanomethane" Angewandte Chemie International Edition 2015. doi:10.1002/anie.201506753

[2] Raamat, E.; Kaupmees, K.; Ovsjannikov, G.; Trummal, A.; Kütt, A.; Saame, J.; Koppel, I.; Kaljurand, I.; Lipping, L.; Rodima, T.; Pihl, V.; Koppel, I. A.; Leito, I. (2013). "Acidities of strong neutral Brønsted acids in different media". J. Phys. Org. Chem. 26 (2): 162–170. doi:10.1002/poc.2946.

[3] Schmidtmann, H. (1896). "Ueber einige Derivate des Malonitrils" (PDF). Berichte der deutschen chemischen Gesellschaft. 29 (2): 1168–1175. doi:10.1002/cber.18960290204.

[4] Šišak, Dubravka; McCusker, Lynne B.; Buckl, Andrea; Wuitschik, Georg; Wu, Yi-Lin; Schweizer, W. Bernd; Dunitz, Jack D. (2010). "The Search for Tricyanomethane (Cyanoform)". Chemistry: A European Journal. 16 (24): 7224–30. doi:10.1002/chem.201000559. PMID 20480465.

[5] Mole, B - Elusive acid finally created https://www.sciencenews.org/article/elusive-acid-finally-created

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