Tricarbon: Difference between revisions
Triatomic elements |
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=== Chemical properties === |
=== 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>{{Cite journal| |
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 === |
=== 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">{{ |
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 == |
== 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. |
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 |
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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== See also == |
== See also == |
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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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Revision as of 16:58, 9 February 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)
|
|
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| 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 alkanylidenes
|
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
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.[citation needed]
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.[1]
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.[2] In contrast to the linear tricarbon molecule, the C+
3 cation is bent.
Nomenclature
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.[1]
See also
References
- ^ 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
- 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.
