Dicarbon monoxide: Difference between revisions

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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

| CASNo_Ref = {{cascite|correct|??}}

| PubChem = 189691

| ChemSpiderID = 164756

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| = {{|correct|chemspider}}

| InChI = 1S/C2O/c1-2-3

| InChIKey = VILAVOFMIJHSJA-UHFFFAOYSA-N}}

|Section2={{Chembox Properties

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| 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 |=Anderson D. J. Rosenfeld R. N. | title= Photodissociation of Carbon Suboxide| journal= [[Journal of Chemical Physics]]| volume=94| year=1991 | issue=12| pages=|doi=10.1063/1.460121}}</ref>

It is stable enough to observe reactions with [[nitric oxide|NO]] and [[nitrogen dioxide|NO₂]].<ref>{{cite journal |=Thweatt W. D. Erickson M. A. Hershberger J. F. | title= Kinetics of the CCO+NO and CCO+ reactions| journal= [[Journal of Physical Chemistry]] | =| = | issue= 1| pages=74–79|doi=10.1021/jp0304125}}</ref>

Called '''ketenylidene''' in [[organometallic chemistry]], it is a [[ligand]] observed in [[metal carbonyl cluster]]s, 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.<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]] (C₆H₅)₃PCCO (CAS# 15596-07-3) contains the C₂O 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>

{{Oxides}}

{{Molecules detected in outer space}}

[[Category:Carbenes]]