Cyclo(6)carbon
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| Names | |
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| Preferred IUPAC name
Hexadehydrobenzene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6 | |
| Molar mass | 72.066 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclo[6]carbon is an allotrope of carbon with molecular formula C6. This theoretical molecule is a ring of six carbon atoms, connected by alternating double bonds.[1] It is, therefore, a member of the cyclo[n]carbon family.
There have been a few attempts to synthesize cyclo[6]carbon, e.g. by pyrolysis of mellitic anhydride,[2] but without success until 2023, when it was successfully synthesised by atom manipulation of hexachlorobenzene, although more thorough research has yet to be reported in peer reviewed scientific work.[1] The molecule's structure presents double bonds in sequence in a bent fashion, which is not explained by valence bond theory for organic molecules, that describes double bonds by combinations of hybridised sp2 orbitals, limiting the molecule's geometry in terms of increase of energy due to bond angles. Cyclo[6]carbon would present then low probability of formation due to its high energy state from a thermodynamical perspective, which is reflected on the lack of evidence of its successful synthesis.
Calculations suggest that the alternative cyclic cumulene structure, called cyclohexahexaene, is the potential energy minimum of the cyclo[6]carbon framework.[3]
References
[edit]- ^ a b Xu, Wei; Sun, Luye; Zheng, Wei; Gao, Wenze; Kang, Faming (2023-10-05), On-surface synthesis of anti-aromatic cyclo[12]carbon and aromatic cyclo[6]carbon (PDF), doi:10.21203/rs.3.rs-3411973/v1
- ^ Fields, Ellis K.; Meyerson, Seymour (October 1966). "Arynes by Pyrolysis of Acid Anhydrides". J. Org. Chem. 31 (10): 3307–3309. doi:10.1021/jo01348a046.
- ^ Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (October 1994). "Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes". Journal of Molecular Structure: THEOCHEM. 313 (3): 335–349. doi:10.1016/0166-1280(94)85015-1.
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