Dicarbon monoxide

Dicarbon monoxide  | Stick model of dicarbon monoxide | Spacefill model of dicarbon monoxide

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Ball and stick model of dicarbon monoxide
Names
IUPAC name

2-Oxoethenylidene

Other names

Ketenylidene

Identifiers

CAS Number

* 119754-08-4 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 164756 Y

PubChem CID

* 189691

CompTox Dashboard (EPA)

* DTXSID80152576

InChI

* InChI=1S/C2O/c1-2-3 Y

Key: VILAVOFMIJHSJA-UHFFFAOYSA-N Y

* 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).

Y verify (what is YN ?)

Infobox references

Chemical compound

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

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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

[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\. 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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Oxocarbons

Common oxides|

* CO
* CO2

Exotic oxides|

* CO3
* CO4
* CO5
* CO6
* C2O
* C2O2
* C2O3
* C2O4 (1,2-Dioxetanedione and 1,3-Dioxetanedione)
* C3O
* C3O2
* C3O3
* C3O6
* C4O2
* C4O4
* C4O6
* C5O2
* C5O5
* C6O6 (Cyclohexanehexone and Ethylenetetracarboxylic dianhydride)
* C8O8
* C9O9
* C10O8
* C10O10
* C12O6
* C12O9
* C12O12

Polymers|

* Graphite oxide
* C3O2
* CO
* CO2

Compounds derived from oxides|

* Metal carbonyls
* Carbonic acid
* Bicarbonates
* Carbonates
* Polycarbonates (Dicarbonates and Tricarbonates)
* Peroxydicarbonates

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Oxides

Mixed oxidation states|

* Antimony tetroxide (Sb2O4)
* Boron suboxide (B12O2)
* Carbon suboxide (C3O2)
* Chlorine perchlorate (Cl2O4)
* Chloryl perchlorate (Cl2O6)
* Cobalt(II,III) oxide (Co3O4)
* Dichlorine pentoxide (Cl2O5)
* Iron(II,III) oxide (Fe3O4)
* Lead(II,IV) oxide (Pb3O4)
* Manganese(II,III) oxide (Mn3O4)
* Mellitic anhydride (C12O9)
* Praseodymium(III,IV) oxide (Pr6O11)
* Silver(I,III) oxide (Ag2O2)
* Terbium(III,IV) oxide (Tb4O7)
* Tribromine octoxide (Br3O8)
* Triuranium octoxide (U3O8)

+1 oxidation state|

* Aluminium(I) oxide (Al2O)
* Copper(I) oxide (Cu2O)
* Caesium monoxide (Cs2O)
* Dibromine monoxide (Br2O)
* Dicarbon monoxide (C2O)
* Dichlorine monoxide (Cl2O)
* Gallium(I) oxide (Ga2O)
* Iodine(I) oxide (I2O)
* Lithium oxide (Li2O)
* Mercury(I) oxide (Hg2O)
* Nitrous oxide (N2O)
* Potassium oxide (K2O)
* Rubidium oxide (Rb2O)
* Silver oxide (Ag2O)
* Thallium(I) oxide (Tl2O)
* Sodium oxide (Na2O)
* Water (hydrogen oxide) (H2O)

+2 oxidation state|

* Aluminium(II) oxide (AlO)
* Barium oxide (BaO)
* Berkelium monoxide (BkO)
* Beryllium oxide (BeO)
* Boron monoxide (BO)
* Bromine monoxide (BrO)
* Cadmium oxide (CdO)
* Calcium oxide (CaO)
* Carbon monoxide (CO)
* Chlorine monoxide (ClO)
* Chromium(II) oxide (CrO)
* Cobalt(II) oxide (CoO)
* Copper(II) oxide (CuO)
* Dinitrogen dioxide (N2O2)
* Disulfur dioxide (S2O2)
* Europium(II) oxide (EuO)
* Germanium monoxide (GeO)
* Iron(II) oxide (FeO)
* Iodine monoxide (IO)
* Lead(II) oxide (PbO)
* Magnesium oxide (MgO)
* Manganese(II) oxide (MnO)
* Mercury(II) oxide (HgO)
* Nickel(II) oxide (NiO)
* Nitric oxide (NO)
* Niobium monoxide (NbO)
* Palladium(II) oxide (PdO)
* Phosphorus monoxide (PO)
* Polonium monoxide (PoO)
* Protactinium monoxide (PaO)
* Radium oxide (RaO)
* Silicon monoxide (SiO)
* Strontium oxide (SrO)
* Sulfur monoxide (SO)
* Thorium monoxide (ThO)
* Tin(II) oxide (SnO)
* Titanium(II) oxide (TiO)
* Vanadium(II) oxide (VO)
* Yttrium(II) oxide (YO)
* Zirconium monoxide (ZrO)
* Zinc oxide (ZnO)

+3 oxidation state|

* Actinium(III) oxide (Ac2O3)
* Aluminium oxide (Al2O3)
* Americium(III) oxide (Am2O3)
* Antimony trioxide (Sb2O3)
* Arsenic trioxide (As2O3)
* Berkelium(III) oxide (Bk2O3)
* Bismuth(III) oxide (Bi2O3)
* Boron trioxide (B2O3)
* Californium(III) oxide (Cf2O3)
* Cerium(III) oxide (Ce2O3)
* Chromium(III) oxide (Cr2O3)
* Cobalt(III) oxide (Co2O3)
* Curium(III) oxide (Cm2O3)
* Dinitrogen trioxide (N2O3)
* Dysprosium(III) oxide (Dy2O3)
* Einsteinium(III) oxide (Es2O3)
* Erbium(III) oxide (Er2O3)
* Europium(III) oxide (Eu2O3)
* Gadolinium(III) oxide (Gd2O3)
* Gallium(III) oxide (Ga2O3)
* Gold(III) oxide (Au2O3)
* Holmium(III) oxide (Ho2O3)
* Indium(III) oxide (In2O3)
* Iron(III) oxide (Fe2O3)
* Lanthanum oxide (La2O3)
* Lutetium(III) oxide (Lu2O3)
* Manganese(III) oxide (Mn2O3)
* Neodymium(III) oxide (Nd2O3)
* Nickel(III) oxide (Ni2O3)
* Phosphorus trioxide (P4O6)
* Praseodymium(III) oxide (Pr2O3)
* Promethium(III) oxide (Pm2O3)
* Rhodium(III) oxide (Rh2O3)
* Samarium(III) oxide (Sm2O3)
* Scandium oxide (Sc2O3)
* Terbium(III) oxide (Tb2O3)
* Thallium(III) oxide (Tl2O3)
* Thulium(III) oxide (Tm2O3)
* Titanium(III) oxide (Ti2O3)
* Tungsten(III) oxide (W2O3)
* Vanadium(III) oxide (V2O3)
* Ytterbium(III) oxide (Yb2O3)
* Yttrium(III) oxide (Y2O3)

+4 oxidation state|

* Americium dioxide (AmO2)
* Berkelium(IV) oxide (BkO2)
* Bromine dioxide (BrO2)
* Californium dioxide (CfO2)
* Carbon dioxide (CO2)
* Carbon trioxide (CO3)
* Cerium(IV) oxide (CeO2)
* Chlorine dioxide (ClO2)
* Chromium(IV) oxide (CrO2)
* Curium(IV) oxide (CmO2)
* Dinitrogen tetroxide (N2O4)
* Germanium dioxide (GeO2)
* Iodine dioxide (IO2)
* Iridium dioxide (IrO2)
* Hafnium(IV) oxide (HfO2)
* Lead dioxide (PbO2)
* Manganese dioxide (MnO2)
* Molybdenum dioxide (MoO2)
* Neptunium(IV) oxide (NpO2)
* Nitrogen dioxide (NO2)
* Niobium dioxide (NbO2)
* Osmium dioxide (OsO2)
* Platinum dioxide (PtO2)
* Plutonium(IV) oxide (PuO2)
* Polonium dioxide (PoO2)
* Praseodymium(IV) oxide (PrO2)
* Protactinium(IV) oxide (PaO2)
* Rhenium(IV) oxide (ReO2)
* Rhodium(IV) oxide (RhO2)
* Ruthenium(IV) oxide (RuO2)
* Selenium dioxide (SeO2)
* Silicon dioxide (SiO2)
* Sulfur dioxide (SO2)
* Technetium(IV) oxide (TcO2)
* Tellurium dioxide (TeO2)
* Terbium(IV) oxide (TbO2)
* Thorium dioxide (ThO2)
* Tin dioxide (SnO2)
* Titanium dioxide (TiO2)
* Tungsten(IV) oxide (WO2)
* Uranium dioxide (UO2)
* Vanadium(IV) oxide (VO2)
* Zirconium dioxide (ZrO2)

+5 oxidation state|

* Antimony pentoxide (Sb2O5)
* Arsenic pentoxide (As2O5)
* Bismuth pentoxide (Bi2O5)
* Dinitrogen pentoxide (N2O5)
* Diuranium pentoxide (U2O5)
* Neptunium(V) oxide (Np2O5)
* Niobium pentoxide (Nb2O5)
* Phosphorus pentoxide (P2O5)
* Protactinium(V) oxide (Pa2O5)
* Tantalum pentoxide (Ta2O5)
* Tungsten pentoxide (W2O5)
* Vanadium(V) oxide (V2O5)

+6 oxidation state|

* Chromium trioxide (CrO3)
* Molybdenum trioxide (MoO3)
* Polonium trioxide (PoO3)
* Rhenium trioxide (ReO3)
* Selenium trioxide (SeO3)
* Sulfur trioxide (SO3)
* Tellurium trioxide (TeO3)
* Tungsten trioxide (WO3)
* Uranium trioxide (UO3)
* Xenon trioxide (XeO3)

+7 oxidation state|

* Dichlorine heptoxide (Cl2O7)
* Manganese heptoxide (Mn2O7)
* Rhenium(VII) oxide (Re2O7)
* Technetium(VII) oxide (Tc2O7)

+8 oxidation state|

* Iridium tetroxide (IrO4)
* Osmium tetroxide (OsO4)
* Ruthenium tetroxide (RuO4)
* Xenon tetroxide (XeO4)
* Hassium tetroxide (HsO4)

Related|

* Oxocarbon
* Suboxide
* Oxyanion
* Ozonide
* Peroxide
* Superoxide
* Oxypnictide

Oxides are sorted by oxidation state. Category:Oxides

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Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium(II) oxide
* Argonium
* Carbon cation
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Cyano radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Imidogen
* Iron(II) oxide
* Magnesium monohydride
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfanyl
* Sulfur mononitride
* Sulfur monoxide
* Titanium(II) oxide

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Triatomic|

* Aluminium(I) hydroxide
* Aluminium isocyanide
* Amino radical
* Carbon dioxide
* Carbonyl sulfide
* CCP radical
* Chloronium
* Diazenylium
* Dicarbon monoxide
* Disilicon carbide
* Ethynyl radical
* Formyl radical
* Hydrogen cyanide (HCN)
* Hydrogen isocyanide (HNC)
* Hydrogen sulfide
* Hydroperoxyl
* Iron cyanide
* Isoformyl
* Magnesium cyanide
* Magnesium isocyanide
* Methylene
* Methylidynephosphane
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Potassium cyanide
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Trihydrogen cation
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanoethynyl
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methyl cation
* Methyl radical
* Methylene amidogen
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thiocyanic acid
* Thioformaldehyde
* Tricarbon monosulfide
* Tricarbon monoxide

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* Cyclopropenone
* Diacetylene
* E-Cyanomethanimine
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methyl isocyanate
* Methylamine
* Propyne
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Acrolein
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Hexapentaenylidene
* Methyl formate
* Methylcyanoacetylene

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Dimethyl ether
* Ethanethiol
* Ethanol
* Methyldiacetylene
* N-Methylformamide
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* Butyronitrile
* C70 fullerene
* Cyanodecapentayne
* Ethyl formate
* Ethylene glycol
* Heptatrienyl radical
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propionaldehyde
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* N2D+
* Propyne
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Glycine
* Graphene
* H2NCO+
* Hemolithin
* Linear C5
* Methoxyethane
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidyne

Related|

* Abiogenesis
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* Homochirality
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* Kerogen
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* Organic compound
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* Tholin

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