Dicarbon monoxide

Dicarbon monoxide
Stick model of dicarbon monoxide	Spacefill model of dicarbon monoxide
Names
	IUPAC name 2-Oxoethenylidene
	Other names Ketenylidene
Identifiers
CAS Number	119754-08-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	164756 ;
PubChem CID	189691;
CompTox Dashboard (EPA)	DTXSID80152576 ;
	InChI InChI=1S/C2O/c1-2-3 Key: VILAVOFMIJHSJA-UHFFFAOYSA-N ; InChI=1S/C2O/c1-2-3 Key: VILAVOFMIJHSJA-UHFFFAOYSA-N; InChI=1/C2O/c1-2-3 Key: VILAVOFMIJHSJA-UHFFFAOYAI;
	SMILES [C]=C=O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

^ 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
^ Bayes, K. (1961). "Photolysis of Carbon Suboxide". Journal of the American Chemical Society. 83 (17): 3712–3713. 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. "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
^ 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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[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. 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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