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Tricarbon

Names
IUPAC name Tricarbon
Systematic IUPAC name 1λ,3λ-propadiene
Other names Triatomic carbon
Identifiers
CAS Number	12075-35-3
3D model (JSmol)	Interactive image
ChemSpider	4937270
PubChem CID	6432003
CompTox Dashboard (EPA)	DTXSID801027035
InChI InChI=1S/C3/c1-3-2Key: NVLRFXKSQQPKAD-UHFFFAOYSA-N
SMILES =C=
Properties
Chemical formula	C3
Molar mass	36.033 g·mol
Thermochemistry
Std molar entropy (S298)	237.27 J K mol
Std enthalpy of formation (ΔfH298)	820.06 kJ mol
Related compounds
Related carbon molecules	Diatomic carbon
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Tricarbon (systematically named 1λ,3λ-propadiene and catena-tricarbon) is an inorganic compound with the chemical formula C
₂(μ-C) (also written or C
₃). It is a colourless gas that only persists in dilution or solution as an adduct. It is one of the simplest unsaturated carbenes. Tricarbon can be found in interstellar space and can be produced in the laboratory by a process called laser ablation.

Natural occurrence

Tricarbon is a small carbon cluster first spectroscopically observed in the early 20th century in the tail of a comet by William Huggins and subsequently identified in stellar atmospheres. Small carbon clusters like tricarbon and dicarbon are regarded as soot precursors and are implicated in the formation of certain industrial diamonds and in the formation of fullerenes.

C₃ has also been identified as a transient species in various combustion reactions.

Properties

Chemical properties

The chemical properties of C₃ was investigated in the 1960s by Professor Emeritus Philip S. Skell of Pennsylvania State University, who showed that certain reactions of carbon vapor indicated its generation, such as the reaction with isobutylene to produce 1,1,1',1'-tetramethyl-bis-ethanoallene.

Physical properties

The ground state molecular geometry of tricarbon has been identified as linear via its characteristic symmetric and antisymmetric stretching and bending vibrational modes and bears bond lengths of 129 to 130 picometer corresponding to those of alkenes. The ionization potential is determined experimentally at 11 to 13.5 electronvolts. In contrast to the linear tricarbon molecule, the C
₃ cation is bent.

Nomenclature

The systematic names 1λ,3λ-propadiene, and μ-carbidodicarbon, valid IUPAC names, are constructed according to the substitutive and additive nomenclatures, respectively.

In appropriate contexts, tricarbon can be viewed as propadiene with four hydrogen atoms removed, or as propane with eight hydrogen atoms removed; and as such, propadienediylidene or propanetetraylidene, respectively, may be used as a context-specific systematic names, according to substitutive nomenclature. By default, these names pay no regard to the radicality of the tricarbon molecule. In even more specific context, these can also name the non-radical singlet state, whereas the diradical state is named propadienediylylidene, or propanediyldiylidene, and the tetraradical state is named propedienetetrayl or propanetetraylylidene.

See also

• Hydrocarbons
• Alkenes
• List of molecules in interstellar space
• Cyclopropatriene

References

1. Gaydon, Alfred G.; Wolfhard, Hans G. (1979). "Detection of intermediate products". Flames: their structure, radiation and temperature (4th rev. ed.). London: Chapman and Hall. ISBN 0-412-15390-4.
2. ^ Skell, P. S.; Wescott, L. D. (1963). "Chemical Properties of C 3 , a Dicarbene". Journal of the American Chemical Society. 85 (7): 1023. doi:10.1021/ja00890a059. ISSN 0002-7863.
3. Nicolas, Christophe; et al. (2006). "Vacuum Ultraviolet Photoionization of C₃". Journal of the American Chemical Society. 128 (1): 220–226. doi:10.1021/ja055430+. PMID 16390150.

Further reading

• Gaydon, Alfred G.; Wolfhard, Hans G. (1979). Flames: their structure, radiation and temperature (4th rev. ed.). London: Chapman and Hall. ISBN 0-412-15390-4.
• Hinkle, Kenneth W.; Keady, John J.; Bernath, Peter F. (1988). "Detection of C₃ in the Circumstellar Shell of IRC+10216". Science. 241 (4871): 1319–1322. Bibcode:1988Sci...241.1319H. doi:10.1126/science.241.4871.1319. PMID 17828935. S2CID 40349500.

v t e 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 Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide 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 N2H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid 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 E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nine atoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
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