Dicarbon monoxide

Dicarbon monoxide
Stick model of dicarbon monoxide
Stick model of dicarbon monoxide
Spacefill model of dicarbon monoxide
Spacefill model of dicarbon monoxide
Ball and stick model of dicarbon monoxide
Ball and stick model of dicarbon monoxide
Names
IUPAC name
2-Oxoethenylidene
Other names
Ketenylidene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2O/c1-2-3 checkY
    Key: VILAVOFMIJHSJA-UHFFFAOYSA-N checkY
  • 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 which, 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 a carbene, an allene, and an oxocarbon.

Occurrence

Dicarbon monoxide is a product of the photolysis of carbon suboxide:

C3O2 → CO + C2O

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

Called ketenylidene in organometallic chemistry, it is a ligand observed in metal carbonyl clusters, e.g. [Co3(CO)9CCO]+ (a modified methylidynetricobaltnonacarbonyl). Ketenylidenes are proposed as intermediates in the chain growth mechanism of the Fischer–Tropsch process, which converts carbon monoxide and hydrogen into hydrocarbon fuels.

The organophosphorus compound (triphenylphosphoranylidene)ketene (C6H5)3PCCO (CAS# 15596-07-3) contains one CCO functional group. Sometimes called Bestmann ylide, it is a yellow solid.

References

  1. ↑ Frenking, Gernot; Tonner, Ralf (2009). "Divalent carbon(0) compounds". Pure and Applied Chemistry. 81 (4): 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. (1992). "CC and CO transformations in ketenylidene cluster compounds". Journal of Molecular Catalysis. 74 (1–3): 73–84. doi:10.1016/0304-5102(92)80225-6.
  6. ↑ Bestmann, Hans Jürgen; Zimmermann, Reiner; Riou, Maxime (2011). "Ketenylidenetriphenylphosphorane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rk005.pub2. ISBN 978-0-471-93623-7.