Dihydroxymethylidene
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| Names | |||
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IUPAC name
Dihydroxymethylidene
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Systematic IUPAC name
Dihydroxymethylidene (substitutive)
Dihydroxidocarbon(2•) (additive) |
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| Other names
Carbonic(II) acid
Carbonous acid |
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| Identifiers | |||
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3D model (JSmol)
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| ChemSpider | |||
| MeSH | Dihydroxycarbene | ||
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PubChem CID
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| Properties | |||
| CH2O2 | |||
| Molar mass | 46.03 g·mol−1 | ||
| Related compounds | |||
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Related compounds
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Formic acid |
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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 | |||
Carbonous acid
Dihydroxycarbene
Lead(II) hydroxide
Orthocarbonic acid
Tin(II) hydroxide
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. Many related carbenes are known, although they are often transient.
Dihydroxymethylidene is produced in the gas phase by high vacuum flash vacuum pyrolysis of oxalic acid:
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 conjugate base of dihydroxycarbene is the carbonite anion, [CO2]2−. Alkali metal salts, e.g., Li
2CO
2, K
2CO
2, and Cs
2CO
2, have been observed at 15K. Salts of the carbonite ion would be protonated to form formic acid, rather than the carbene.
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