Benzotriyne
Encyclopedia
Benzotriyne or cyclo[6]carbon is a hypothetical chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

, an allotrope of carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 with molecular formula C6. The molecule is a ring of six carbon atoms, connected either by alternating triple and single bonds or by double bonds. 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
Pyrolysis
Pyrolysis is a thermochemical decomposition of organic material at elevated temperatures without the participation of oxygen. It involves the simultaneous change of chemical composition and physical phase, and is irreversible...

 of mellitic anhydride
Mellitic anhydride
Mellitic anhydride, anhydride of mellitic acid, is organic compound with formula C12O9.Mellitic anhydride is oxide of carbon , like CO2, CO, and C3O2. It is white sublimable solid, apparently obtained by Liebig and Wöhler in 1830 in their study of mellite , who assigned it the formula C4O3. The...

, but without success (as of 2011).

Recent investigations have concluded that benzotriyne is unlikely to exist due to the large angle strain. A likely alternative would be a cyclical cumulene
Cumulene
A cumulene is a chemical compound with two or more cumulative double bonds, for example butatriene , H2C=C=C=CH2. Unlike alkanes and most alkenes, cumulenes tend to be rigid, which makes them appealing for molecular nanotechnology. Polyynes are another kind of rigid carbon chains...

 called cyclohexahexaene which, itself should be a metastable species.
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