Fulminic acid

Fulminic acid
Names
	IUPAC name Oxidoazaniumylidynemethane
Identifiers
CAS Number	506-85-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29813 ;
ChEMBL	ChEMBL185198 ;
ChemSpider	454715 ;
PubChem CID	521293;
CompTox Dashboard (EPA)	DTXSID30334603 ;
	InChI InChI=1S/CHNO/c1-2-3/h1H Key: UXKUODQYLDZXDL-UHFFFAOYSA-N ; InChI=1/CHNO/c1-2-3/h1H Key: UXKUODQYLDZXDL-UHFFFAOYAL;
	SMILES [O-][N+]#C;
Properties
Chemical formula	HCNO
Molar mass	43.02 g mol−1
Conjugate base	Fulminate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Fulminic acid, chemical formula HCNO, was first isolated in 1966.[1]

A more convenient synthesis involves flash pyrolysis of certain oximes. In contrast to earlier syntheses, this method avoids the use of highly explosive metal fulminates.[2]

The structure of the molecule has been determined by microwave spectroscopy with the following bond-lengths - C-H: 1.027(1)Å, C-N: 1.161(15)Å, N-O: 1.207(15)Å.[3]

References

Beck, W. and Feldl, K. (1966), The Structure of Fulminic Acid, HCNO. Angew. Chem. Int. Ed. Engl., 5: 722–723. doi:10.1002/anie.196607221
Wentrup, Curt; Gerecht, Bernd; Horst, Briehl (1979). "A New Synthesis of Fulminic Acid". Angew. Chem. 18 (6): 467–468. doi:10.1002/anie.197904671.
Winnewisser, Manfred; Bodenseh, Hans Karl (1967). "Mikrowellenspektrum, Struktur und /-Typ-Dublett-Aufspaltung der HCNO (Knallsäure)". Z. Naturforsch. 22 a: 1724–1737.

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[1] Beck, W. and Feldl, K. (1966), The Structure of Fulminic Acid, HCNO. Angew. Chem. Int. Ed. Engl., 5: 722–723. doi:10.1002/anie.196607221

[2] Wentrup, Curt; Gerecht, Bernd; Horst, Briehl (1979). "A New Synthesis of Fulminic Acid". Angew. Chem. 18 (6): 467–468. doi:10.1002/anie.197904671.

[3] Winnewisser, Manfred; Bodenseh, Hans Karl (1967). "Mikrowellenspektrum, Struktur und /-Typ-Dublett-Aufspaltung der HCNO (Knallsäure)". Z. Naturforsch. 22 a: 1724–1737.