Benzotriyne
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| Names | |
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| Preferred IUPAC name
Hexadehydrobenzene | |
| Identifiers | |
3D model (JSmol)
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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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| Infobox references | |
Benzotriyne or cyclo[6]carbon is a hypothetical chemical compound, an allotrope of carbon with molecular formula C6. The molecule is a ring of six carbon atoms, connected by alternating triple and single bonds.[1] It is, therefore, a potential member of the cyclo[n]carbon family.
There have been a few attempts to synthesize benzotriyne, e.g. by pyrolysis of mellitic anhydride,[2] but without success as of 2011.
Recent investigations have concluded that benzotriyne is unlikely to exist due to the large angle strain.[citation needed] A likely alternative isomer would be a cyclic cumulene called cyclohexahexaene, which should itself be a metastable species.
The name cracatene was suggested for this compound (after Karel Čapek's Krakatit, a hypothetical explosive).[3]
References[]
- ^ Adamson, George A.; Rees, Charles W. (1996). "Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon". J. Chem. Soc., Perkin Trans. 1 (13): 1535–1543. doi:10.1039/P19960001535.
- ^ 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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- Hypothetical chemical compounds
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