View source for 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 = 
  }}
}}

'''Dicarbon monoxide''' ({{chem2|C2O}}) is a [[molecule]] that contains two [[carbon]] [[atom]]s 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 [[Reactivity (chemistry)|reactive]] that it is not encountered in everyday life.  It is classified as a [[carbene]], [[cumulene]] and an [[oxocarbon]].<ref>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}}</ref>

==Occurrence==
Dicarbon monoxide is a product of the [[Photodissociation|photolysis]] of [[carbon suboxide]]:<ref>{{ 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 }}</ref><ref>{{ 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 }}</ref>

:C<sub>3</sub>O<sub>2</sub>  → CO  + C<sub>2</sub>O

It is stable enough to observe reactions with [[nitric oxide|NO]] and [[nitrogen dioxide|NO<sub>2</sub>]].<ref>{{ cite journal |author1=Thweatt, W. D. |author2=Erickson, M. A. |author3=Hershberger, J. F. | title = Kinetics of the CCO + NO and CCO + NO<sub>2</sub> reactions | journal = [[Journal of Physical Chemistry A]] | year = 2004 | volume = 108 | issue = 1 | pages = 74–79 | doi = 10.1021/jp0304125 |bibcode=2004JPCA..108...74T }}</ref>

Called '''ketenylidene''' in [[organometallic chemistry]], it is a [[ligand]] observed in [[metal carbonyl cluster]]s, e.g. [OC<sub>2</sub>Co<sub>3</sub>(CO)<sub>9</sub>]<sup>+</sup>.  Ketenylidenes are proposed as intermediates in the chain growth mechanism of the [[Fischer-Tropsch Process]], which converts [[carbon monoxide]] and [[hydrogen]] to hydrocarbon fuels.<ref>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}}</ref>

The [[organophosphorus compound]] (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PCCO (CAS# 15596-07-3) contains the C<sub>2</sub>O functionality.  Sometimes called Bestmann's Ylide, it is a yellow solid.<ref>H. J. Bestmann, R. Zimmermann, M. Riou "Ketenylidenetriphenylphosphorane" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001. {{doi| 10.1002/047084289X.rk005.pub2}}</ref>

==References==
{{reflist}}
{{Oxides of carbon}}
{{Oxides}}
{{Molecules detected in outer space}}

[[Category:Carbenes]]
[[Category:Oxocarbons]]

{{Inorganic-compound-stub}}