Dicarbon monoxide

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Dicarbon monoxide
Stick model of dicarbon monoxide Dicarbon-monoxide-2D.svg
Stick model of dicarbon monoxide
Spacefill model of dicarbon monoxide Dicarbon-monoxide-3D-vdW.png
Spacefill model of dicarbon monoxide
Ball and stick model of dicarbon monoxide Dicarbon-monoxide-3D-balls.png
Ball and stick model of dicarbon monoxide
Names
IUPAC name
2-Oxoethenylidene
Other names
Ketenylidene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C2O/c1-2-3 Yes check.svgY
    Key: VILAVOFMIJHSJA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C2O/c1-2-3
    Key: VILAVOFMIJHSJA-UHFFFAOYSA-N
  • InChI=1/C2O/c1-2-3
    Key: VILAVOFMIJHSJA-UHFFFAOYAI
  • [C]=C=O
Properties
C2O
Molar mass 40.021 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dicarbon monoxide (C2O) is a 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 carbene, 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
  2. ↑ Bayes, K. (1961). "Photolysis of Carbon Suboxide". Journal of the American Chemical Society . 83 (17): 3712–3713. Bibcode:1961JAChS..83.3712B. doi:10.1021/ja01478a033.
  3. ↑ Anderson, D. J.; Rosenfeld, R. N. (1991). "Photodissociation of Carbon Suboxide". Journal of Chemical Physics . 94 (12): 7857–7867. doi:10.1063/1.460121.
  4. ↑ Thweatt, W. D.; Erickson, M. A.; Hershberger, J. F. (2004). "Kinetics of the CCO + NO and CCO + NO2 reactions". Journal of Physical Chemistry A . 108 (1): 74–79. Bibcode:2004JPCA..108...74T. doi:10.1021/jp0304125.
  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
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