Dicarbon monoxide
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| Names | |||
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| IUPAC name
2-Oxoethenylidene | |||
| Other names
Ketenylidene | |||
| Identifiers | |||
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| 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.[1]
Occurrence
[edit]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. [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.[5]
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.[6]
References
[edit]- ↑ 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.
- ↑ 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.
- ↑ Anderson, D. J.; Rosenfeld, R. N. (1991). "Photodissociation of Carbon Suboxide". Journal of Chemical Physics. 94 (12): 7857–7867. doi:10.1063/1.460121.
- ↑ 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.
- ↑ 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.
- ↑ 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.
