Fulminic acid
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IUPAC name Oxidoazaniumylidynemethane | |
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3D model (JSmol) |
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Beilstein Reference | 1071209 |
ChEBI |
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ChEMBL |
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ChemSpider |
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Gmelin Reference | 772 |
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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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). Y verify (what is YN ?) Infobox references |
Fulminic acid is an acid with the formula HCNO, more specifically H−C≡N+−O−. It is an isomer of isocyanic acid (H−N=C=O) and of its elusive tautomer, cyanic acid (H−O−C≡N), and also of isofulminic acid (H−O−N+≡C−).[1]
Fulminate is the anion [C−≡N+−O−] or any of its salts. For historical reasons, the fulminate functional group is understood to be −O−N+≡C− as in isofulminic acid;[2] whereas the group −C≡N+O− is called nitrile oxide.
History
This chemical was known since the early 1800s through its salts and via the products of reactions in which it was proposed to exist,[3] but the acid itself was not detected until 1966.[1]
Structure
Fulminic acid was long believed to have a structure of H–O–N+≡C−. It wasn't until the 1966 isolation and analysis of a pure sample of fulminic acid that this structural idea was conclusively disproven.[3] The chemical that actually has that structure, isofulminic acid (a tautomer of the actual fulminic acid structure) was eventually detected in 1988.[3]
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.[4]
Synthesis
A convenient synthesis involves flash pyrolysis of certain oximes. In contrast to earlier syntheses, this method avoids the use of highly explosive metal fulminates.[5]
References
- ^ a b Beck, W.; Feldl, K. (1966). "The Structure of Fulminic Acid, HCNO". Angew. Chem. Int. Ed. Engl. 5 (8): 722–723. doi:10.1002/anie.196607221.
- ^ Wentrup, Curt; Gerecht, Bernd; Laqua, Dieter; Briehl, Horst; Winter, Hans Wilhelm; Reisenauer, Hans Peter; Winnewisser, Manfred (1981). "Organic fulminates, R-O-NC". Journal of Organic Chemistry. 46 (5): 1046–1048. doi:10.1021/jo00318a050.
- ^ a b c Kurzer, Frederick (2000). "Fulminic Acid in the History of Organic Chemistry". Journal of Chemical Education. 77 (7): 851–857. Bibcode:2000JChEd..77..851K. doi:10.1021/ed077p851.
- ^ Winnewisser, Manfred; Bodenseh, Hans Karl (1967). "Mikrowellenspektrum, Struktur und /-Typ-Dublett-Aufspaltung der HCNO (Knallsäure)". Z. Naturforsch. 22 a (11): 1724–1737. Bibcode:1967ZNatA..22.1724W. doi:10.1515/zna-1967-1109. S2CID 96725880.
- ^ Wentrup, Curt; Gerecht, Bernd; Horst, Briehl (1979). "A New Synthesis of Fulminic Acid". Angew. Chem. 18 (6): 467–468. doi:10.1002/anie.197904671.
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- H3AsO3
- H3AsO4
- HArF
- HAt
- HSO3F
- H[BF4]
- HBr
- HBrO
- HBrO2
- HBrO3
- HBrO4
- HCl
- HClO
- HClO2
- HClO3
- HClO4
- HCN
- HCNO
- H2CrO4/H2Cr2O7
- H2CO3
- H2CS3
- HF
- HFO
- HI
- HIO
- HIO2
- HIO3
- HIO4
- HMnO4
- H2MnO4
- H2MoO4
- HNC
- NaHCO3
- HNCO
- HNO
- HNO2
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- H2N2O2
- HNO5S
- H3NSO3
- H2O
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- H2O3
- H2O4
- H2O5
- H3PO2
- H3PO3
- H3PO4
- H4P2O7
- H5P3O10
- H2[PtCl6]
- H2S
- H2S2
- H2Se
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- H2SeO4
- H4SiO4
- H2[SiF6]
- HSCN
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- H2SO5
- H2S2O3
- H3O
- H2S2O6
- H2S2O7
- H2S2O8
- CF3SO3H
- H2Te
- H2TeO3
- H6TeO6
- H4TiO4
- H2Po
- H[Co(CO)4]
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