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Dicarbon monoxide

From Wikipedia, the free encyclopedia
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 mass40.021 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Dicarbon monoxide (C2O) is amolecule that contains twocarbonatoms and oneoxygen atom. It is alinear molecule that, because of its simplicity, is of interest in a variety of areas. It is, however, so extremelyreactive that it is not encountered in everyday life. It is classified as acarbene,cumulene and anoxocarbon.[1]

Occurrence

[edit]

Dicarbon monoxide is a product of thephotolysis ofcarbon suboxide:[2][3]

C3O2 → CO + C2O

It is stable enough to observe reactions withNO andNO2.[4]

Calledketenylidene inorganometallic chemistry, it is aligand observed inmetal carbonyl clusters, e.g. [OC2Co3(CO)9]+. Ketenylidenes are proposed as intermediates in the chain growth mechanism of theFischer-Tropsch Process, which convertscarbon monoxide andhydrogen to hydrocarbon fuels.[5]

Theorganophosphorus compound (C6H5)3PCCO (CAS# 15596-07-3) contains the C2O functionality. Sometimes called Bestmann's Ylide, it is a yellow solid.[6]

References

[edit]
  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.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. "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
Common oxides
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Mixed oxidation states
+1 oxidation state
+2 oxidation state
+3 oxidation state
+4 oxidation state
+5 oxidation state
+6 oxidation state
+7 oxidation state
+8 oxidation state
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