Dicarbon monoxide

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title: "Dicarbon monoxide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["carbenes", "oxocarbons"] topic_path: "general/carbenes" source: "https://en.wikipedia.org/wiki/Dicarbon_monoxide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | CASNo = 119754-08-4 | PubChem = 189691 | ChemSpiderID = 164756 | ChemSpiderID_Ref = | StdInChI_Ref = | StdInChI = 1S/C2O/c1-2-3 | StdInChIKey_Ref = | 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 () 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.

Occurrence

Dicarbon monoxide is a product of the photolysis of carbon suboxide:

:C3O2 → CO + C2O

It is stable enough to observe reactions with NO and NO2.

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.

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

References

References

  1. (2009). "Divalent carbon(0) compounds". Pure and Applied Chemistry.
  2. Bayes, K.. (1961). "Photolysis of Carbon Suboxide". [[Journal of the American Chemical Society]].
  3. (1991). "Photodissociation of Carbon Suboxide". [[Journal of Chemical Physics]].
  4. (2004). "Kinetics of the CCO + NO and CCO + NO2 reactions". [[Journal of Physical Chemistry A]].
  5. (1992). "CC and CO transformations in ketenylidene cluster compounds". Journal of Molecular Catalysis.
  6. (2011). "Encyclopedia of Reagents for Organic Synthesis".

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carbenesoxocarbons