Dicarbon monoxide

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
CAS Number	119754-08-4 checkY
3D model (JSmol)	Interactive image
ChemSpider	164756 checkY
ECHA InfoCard
E number
PubChem CID	189691
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI 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
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). checkY verify (what is checkY☒N ?) 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.

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.