Carbon suboxide

Carbon suboxide, or tricarbon dioxide, is an organic, oxygen-containing chemical compound with formula C3O2 and structure O=C=C=C=O. Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons O=Cn=O, which also includes carbon dioxide (CO2) and pentacarbon dioxide (C5O2). Although if carefully purified it can exist at room temperature in the dark without decomposing, it will polymerize under certain conditions.

Carbon suboxide
Names
Preferred IUPAC name
Propa-1,2-diene-1,3-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Carbon+suboxide
PubChem CID
UNII
  • InChI=1S/C3O2/c4-2-1-3-5 Y
    Key: GNEVIACKFGQMHB-UHFFFAOYSA-N Y
  • InChI=1/C3O2/c4-2-1-3-5
    Key: GNEVIACKFGQMHB-UHFFFAOYAU
SMILES
  • O=C=C=C=O
Properties
C3O2
Molar mass 68.031 g·mol−1
Appearance colorless gas
Odor strong, pungent odor
Density 3.0 kg/m3, gas

1.114 g/cm3, liquid

Melting point −111.3 °C (−168.3 °F; 161.8 K)
Boiling point 6.8 °C (44.2 °F; 279.9 K)
reacts
Solubility soluble in 1,4-dioxane, ether, xylene, CS2, tetrahydrofuran
Refractive index (nD)
1.4538 (6 °C)
0 D
Structure
rhombic
Molecular shape
quasilinear (phase dependent)
Thermochemistry
66.99 J/mol K
Std molar
entropy (S298)
276.1 J/mol K
Std enthalpy of
formation fH298)
−93.6 kJ/mol
Related compounds
Related oxides
carbon dioxide
carbon monoxide
dicarbon monoxide
Related compounds
carbon subsulfide
carbon subnitride
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

The substance was discovered in 1873 by Benjamin Brodie by subjecting carbon monoxide to an electric current. He claimed that the product was part of a series of "oxycarbons" with formulas Cx+1Ox, namely C2O, C3O2, C4O3, C5O4, …, and to have identified the last two; however, only C3O2 is known. In 1891 Marcellin Berthelot observed that heating pure carbon monoxide at about 550 °C created small amounts of carbon dioxide but no trace of carbon, and assumed that a carbon-rich oxide was created instead, which he named "sub-oxide". He assumed it was the same product obtained by electric discharge and proposed the formula C2O. Otto Diels later stated that the more organic names dicarbonylmethane and dioxallene were also correct.

It is commonly described as an oily liquid or gas at room temperature with an extremely noxious odor.

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