Tricarbon: Difference between revisions
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| ImageFile = Tricarbon.svg |
| ImageFile = Tricarbon.svg |
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| ImageFile1 = Tricarbon-3D-vdW.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = 100 |
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| ImageName = Skeletal formula of tricarbon with all lone pairs shown |
| ImageName = Skeletal formula of tricarbon with all lone pairs shown |
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| OtherNames = Triatomic carbon{{Citation needed|date=May 2012}} |
| OtherNames = Triatomic carbon{{Citation needed|date=May 2012}} |
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| IUPACName = Tricarbon |
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| SystematicName = 1λ<sup>2</sup>,3λ<sup>2</sup>-propadiene |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| CASNo = 12075-35-3 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem = 6432003 |
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| PubChem_Ref = {{Pubchemcite|correct|Pubchem}} |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=3 |
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| ExactMass = 36.000000000000 g mol<sup>−1</sup> |
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| Section3 = {{Chembox Thermochemistry |
| Section3 = {{Chembox Thermochemistry |
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| DeltaHf = 820.06 kJ mol<sup>−1</sup> |
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| Entropy = 237.27 J K<sup>−1</sup> mol<sup>−1</sup> |
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| Section4 = {{Chembox Related |
| Section4 = {{Chembox Related |
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| OtherFunction_label = carbon molecules |
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| Function = alkanylidenes |
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| OtherFunction = [[Diatomic carbon]] |
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'''Tricarbon''' (systematically named '''1λ<sup>2</sup>,3λ<sup>2</sup>-propadiene''' and '''''catena''-tricarbon''') is an [[inorganic compound]] with the [[chemical formula]] {{Chem|C|2|(μ-C)}} (also written [C(μ-C)C] or {{Chem|C|3}}). It is a colourless gas that only persists in dilution or solution as an [[adduct]]. It is one of the simplest [[saturated and unsaturated compounds|unsaturated]] [[carbene]]s. Tricarbon can be found in interstellar space and can be produced in the laboratory by a process called [[laser ablation]]. |
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C<sub>3</sub> has also been identified as a transient species in various [[combustion]] reactions.{{Citation needed|date=September 2009}} |
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== Natural occurrence == |
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The generation of C<sub>3</sub> was investigated by Professor Emeritus [[Philip Skell|Philip S. Skell]] of [[Pennsylvania State University]] in the 1960s.{{Citation needed|date=September 2009}} |
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Tricarbon is a small [[carbon]] cluster first [[spectroscopy|spectroscopically]] observed in the early 20th century in the tail of a comet by [[William Huggins]] and subsequently identified in [[stellar atmosphere]]s. Small carbon clusters like tricarbon and [[dicarbon]] are regarded as soot precursors and are implicated in the formation of certain industrial [[diamond]]s and in the formation of [[fullerene]]s. |
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C<sub>3</sub> has also been identified as a transient species in various [[combustion]] reactions.<ref>{{Cite book |last=Gaydon |first=Alfred G. |chapter=Detection of intermediate products|title=Flames: their structure, radiation and temperature |last2=Wolfhard, Hans G. |date=1979 |publisher=Chapman and Hall |isbn=0-412-15390-4 |edition=4th rev. |location=London}} |
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</ref>{{rp|218–220, plate 20}} |
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== Properties == |
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=== Chemical properties === |
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The chemical properties of C<sub>3</sub> was investigated in the 1960s by Professor Emeritus [[Philip Skell|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.<ref name="Skell">{{Cite journal |last=Skell |first=P. S. |last2=Wescott |first2=L. D. |date=1963 |title=Chemical Properties of C 3 , a Dicarbene |url=https://pubs.acs.org/doi/abs/10.1021/ja00890a059 |journal=Journal of the American Chemical Society |language=en |volume=85 |issue=7 |pages=1023 |doi=10.1021/ja00890a059 |issn=0002-7863}}</ref> |
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=== Physical properties === |
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| ⚫ | 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 length]]s of 129 to 130 [[picometer]] corresponding to those of [[alkene]]s. The [[ionization potential]] is determined experimentally at 11 to 13.5 [[electronvolt]]s.<ref name="Nicolas">{{Cite journal |last=Nicolas |first=Christophe |display-authors=etal |date=2006 |title=Vacuum Ultraviolet Photoionization of C<sub>3</sub> |journal=[[Journal of the American Chemical Society]] |volume=128 |issue=1 |pages=220–226 |doi=10.1021/ja055430+ |pmid=16390150}}</ref> In contrast to the linear tricarbon molecule, the {{chem|C|3|+}} [[cation]] is bent. |
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== Nomenclature == |
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The systematic names ''1λ<sup>2</sup>,3λ<sup>2</sup>-propadiene'', and ''μ-carbidodicarbon'', valid [[IUPAC]] names, are constructed according to the substitutive and additive nomenclatures, respectively. |
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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''.<ref name="Skell"/> |
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*[[Hydrocarbons]] |
*[[Hydrocarbons]] |
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*[[Alkene]]s |
*[[Alkene]]s |
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*[[Cyclopropatriene]] |
*[[Cyclopropatriene]] |
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==References== |
== References == |
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{{Reflist}} |
{{Reflist}} |
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==Further reading== |
== Further reading == |
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*{{ |
*{{Cite book |last=Gaydon |first=Alfred G. |title=Flames: their structure, radiation and temperature |last2=Wolfhard, Hans G. |date=1979 |publisher=Chapman and Hall |isbn=0-412-15390-4 |edition=4th rev. |location=London}} |
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*{{ |
*{{Cite journal |last=Hinkle |first=Kenneth W. |last2=Keady, John J. |last3=Bernath, Peter F. |date=1988 |title=Detection of C<sub>3</sub> in the Circumstellar Shell of IRC+10216 |url=https://zenodo.org/record/1230984 |journal=[[Science (journal)|Science]] |volume=241 |issue=4871 |pages=1319–1322 |bibcode=1988Sci...241.1319H |doi=10.1126/science.241.4871.1319 |pmid=17828935 |s2cid=40349500}} |
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{{Allotropes of carbon}} |
{{Allotropes of carbon}} |
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{{Triatomic elements}} |
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{{Molecules detected in outer space}} |
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[[Category:Astrochemistry]] |
[[Category:Astrochemistry]] |
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[[Category:Homonuclear triatomic molecules]] |
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Latest revision as of 21:24, 11 April 2024
 | This article needs additional citations for verification. (September 2009) |
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| Names | |
|---|---|
| IUPAC name
Tricarbon
| |
| Systematic IUPAC name
1λ2,3λ2-propadiene | |
| Other names
Triatomic carbon[citation needed]
| |
| Identifiers | |
3D model (JSmol)
|
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| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
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| |
| Properties | |
| C3 | |
| Molar mass | 36.033 g·mol−1 |
| Thermochemistry | |
Std molar
entropy (S⦵298) |
237.27 J K−1 mol−1 |
Std enthalpy of
formation (ΔfH⦵298) |
820.06 kJ mol−1 |
| Related compounds | |
Related carbon molecules
|
Diatomic carbon |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Tricarbon (systematically named 1λ2,3λ2-propadiene and catena-tricarbon) is an inorganic compound with the chemical formula C
2(μ-C) (also written [C(μ-C)C] 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
[edit]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.[1]: 218–220, plate 20
Properties
[edit]Chemical properties
[edit]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.[2]
Physical properties
[edit]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.[3] In contrast to the linear tricarbon molecule, the C+
3 cation is bent.
Nomenclature
[edit]The systematic names 1λ2,3λ2-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.[2]
See also
[edit]References
[edit]- ^ 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.
- ^ a b 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.
- ^ 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
[edit]- 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.
