Dicarbon monoxide

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Dicarbon monoxide
Stick model of dicarbon monoxide
Spacefill model of dicarbon monoxide
Ball and stick model of dicarbon monoxide
Names
IUPAC name
2-Oxoethenylidene
Other names
Ketenylidene
Identifiers
119754-08-4 YesY
ChemSpider 164756 YesY
Jmol 3D model Interactive image
PubChem 189691
Properties
C2O
Molar mass 40.02 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Dicarbon monoxide (C2O) is molecule that contains two carbon atoms and one oxygen atom. It is a linear molecule that, because of its simplicity, is of interest in a variety of areas. It is, however, so extremely reactive that it is not encountered in everyday life. It is classified as a cumulene and an oxocarbon.[1]

Occurrence

Dicarbon monoxide is a product of the photolysis of carbon suboxide:[2][3]

C3O2 → CO + C2O

It is stable enough to observe reactions with NO and NO2.[4]

Called ketenylidene in organometallic chemistry, it is a ligand observed in metal carbonyl clusters, e.g. [OC2Co3(CO)9]+. Ketenylidenes are proposed as intermediates in the chain growth mechanism of the Fischer-Tropsch Process, which converts carbon monoxide and hydrogen to hydrocarbon fuels.[5]

The organophosphorus compound (C6H5)3PCCO (CAS# 15596-07-3) contains the C2O functionality. Sometimes called Bestmann's Ylide, it is a yellow solid.[6]

References

  1. Frenking, Gernot; Tonner, Ralf "Divalent carbon(0) compounds" Pure and Applied Chemistry 2009, vol. 81, pp. 597-614. doi:10.1351/PAC-CON-08-11-03
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  5. Jensen, Michael P.; Shriver, Duward F. "Carbon-carbon and carbonyl transformations in ketenylidene cluster compounds" Journal of Molecular Catalysis 1992, vol. 74, pp. 73-84. doi:10.1016/0304-5102(92)80225-6
  6. H. J. Bestmann, R. Zimmermann, M. Riou "Ketenylidenetriphenylphosphorane" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001. doi: 10.1002/047084289X.rk005.pub2