:Dicarbon monoxide
{{Chembox
| Watchedfields = changed
| verifiedrevid = 443636285
| ImageFileL1 = Dicarbon-monoxide-2D.svg
| ImageNameL1 = Stick model of dicarbon monoxide
| ImageFileR1 = Dicarbon-monoxide-3D-vdW.png
| ImageNameR1 = Spacefill model of dicarbon monoxide
| ImageFile2 = Dicarbon-monoxide-3D-balls.png
| ImageName2 = Ball and stick model of dicarbon monoxide
| IUPACName = 2-Oxoethenylidene
| OtherNames = Ketenylidene
|Section1={{Chembox Identifiers
| InChI1 = 1/C2O/c1-2-3
| InChIKey1 = VILAVOFMIJHSJA-UHFFFAOYAI
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 119754-08-4
| PubChem = 189691
| ChemSpiderID = 164756
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2O/c1-2-3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VILAVOFMIJHSJA-UHFFFAOYSA-N
| SMILES = [C]=C=O
| InChI = 1S/C2O/c1-2-3
| InChIKey = VILAVOFMIJHSJA-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
| C=2 | O=1
| Solubility =
}}
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Dicarbon monoxide ({{chem2|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.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}}
Occurrence
Dicarbon monoxide is a product of the photolysis of carbon suboxide:{{ cite journal | author= Bayes, K. | title = Photolysis of Carbon Suboxide | journal = Journal of the American Chemical Society | volume = 83 | year = 1961 | issue = 17 | pages = 3712–3713 | doi = 10.1021/ja01478a033 }}{{ cite journal |author1=Anderson, D. J. |author2=Rosenfeld, R. N. | title = Photodissociation of Carbon Suboxide | journal = Journal of Chemical Physics | volume = 94 | year = 1991 | issue = 12 | pages = 7857–7867 | doi = 10.1063/1.460121 }}
:C3O2 → CO + C2O
It is stable enough to observe reactions with NO and NO2.{{ cite journal |author1=Thweatt, W. D. |author2=Erickson, M. A. |author3=Hershberger, J. F. | title = Kinetics of the CCO + NO and CCO + NO2 reactions | journal = Journal of Physical Chemistry A | year = 2004 | volume = 108 | issue = 1 | pages = 74–79 | doi = 10.1021/jp0304125 |bibcode=2004JPCA..108...74T }}
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.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}}
The organophosphorus compound (C6H5)3PCCO (CAS# 15596-07-3) contains the C2O functionality. Sometimes called Bestmann's Ylide, it is a yellow solid.H. J. Bestmann, R. Zimmermann, M. Riou "Ketenylidenetriphenylphosphorane" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001. {{doi| 10.1002/047084289X.rk005.pub2}}
References
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{{Oxides of carbon}}
{{Oxides}}
{{Molecules detected in outer space}}
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