Dihydroxymethylidene

Dihydroxymethylidene is a chemical compound with formula C(OH)2. It is an unstable tautomer of formic acid. There is no evidence that this compound exists in solution, but the molecule has been detected in the gas phase.[1] Many related carbenes are known, although they are often transient.[2]

Dihydroxymethylidene
Structural formula of dihydroxymethylidene
Ball and stick model of dihydroxymethylidene
Names
Preferred IUPAC name
Dihydroxymethylidene
Systematic IUPAC name
Dihydroxymethylidene (substitutive)
Dihydroxidocarbon(2•) (additive)
Other names
Carbonic(II) acid

Carbonous acid
Dihydroxycarbene

Dihydroxymethylene
Identifiers
3D model (JSmol)
ChemSpider
MeSH Dihydroxycarbene
  • InChI=1S/CH2O2/c2-1-3/h2-3H Y
    Key: VZOMUUKAVRPMBY-UHFFFAOYSA-N Y
  • O[C]O
Properties
CH2O2
Molar mass 46.025 g·mol−1
Related compounds
Related compounds
 Formic acid

Lead(II) hydroxide
Orthocarbonic acid
Tin(II) hydroxide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production and properties

Dihydroxymethylidene is produced in the gas phase by high vacuum flash vacuum pyrolysis of oxalic acid:

C2O4H2 → C(OH)2 + CO2

The species is a bent molecule with an O−C−O angle of 105.6° for the C2v all-trans rotamer. Although stable at 10 K, at higher temperatures it isomerizes to formic acid.

The double ionized ion, CO2−
2, is known as the carbonite ion

References
  1. Schreiner, Peter R.; Reisenauer, Hans Peter "Spectroscopic identification of dihydroxycarbene" Angewandte Chemie International Edition (2008), volume 47, 7071-7074. doi:10.1002/anie.200802105
  2. M. Jones, Jr., R. A. Moss, in "Reactive Intermediate Chemistry", Edited by R. A. Moss, M. S. Platz, M. Jones, Jr., Wiley-Interscience, Hoboken, 2004.
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