Fulminic acid

Source: Wikipedia, the free encyclopedia.
Fulminic acid
Names
IUPAC name
Oxidoazaniumylidynemethane
Identifiers
3D model (
JSmol
)
1071209
ChEBI
ChEMBL
ChemSpider
772
  • InChI=1S/CHNO/c1-2-3/h1H checkY
    Key: UXKUODQYLDZXDL-UHFFFAOYSA-N checkY
  • InChI=1/CHNO/c1-2-3/h1H
    Key: UXKUODQYLDZXDL-UHFFFAOYAL
  • [O-][N+]#C
Properties
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).
checkY verify (what is checkY☒N ?)

Fulminic acid is an

cyanic acid (H−O−C≡N), and also of isofulminic acid (H−O−N+≡C−).[1]

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

  1. ^
    doi:10.1002/anie.196607221
    .
  2. doi:10.1021/jo00318a050
    .
  3. ^
    doi:10.1021/ed077p851
    .
  4. S2CID 96725880
    .
  5. doi:10.1002/anie.197904671
    .
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