Mechanisms of the hydrogen atom and the phenyl group migration in the molecule of heptaphenylcycloheptatriene View Full Text


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Article Info

DATE

2012-09

AUTHORS

G. A. Dushenko, I. E. Mikhailov, O. I. Mikhailova, R. M. Minyaev, V. I. Minkin

ABSTRACT

In terms of the density functional theory using the B3LYP functional, 1,2,3,4,5,6,7-heptaphenylcycloheptatriene was shown to be the most stable in the boat conformation of the cycloheptatriene ring with the H atom in the equatorial position. 1,5-Sigmatropic shifts of the H atom along the seven-membered ring perimeter take place when it is in the axial position through the asymmetric transition state with the barrier ΔE≠ZPE = 28.7 kcal mol−1. The H atom can attain the axial position upon inversion of the seven-membered ring, which is accompanied by the orthogonal turn of the phenyl group at the sp3-hybridized C atom (ΔE≠ZPE = 22.6 kcal mol−1). The energy barrier to the circular rearrangement of the H atom (ΔE≠ZPE = 32.2 kcal mol−1) explains formation of isomers during the high-temperature synthesis of di(p-tolyl)pentaphenylcycloheptatriene. The barrier to the 1,5-sigmatropic shifts of the phenyl group is 19.7 kcal mol−1 higher than that for the competing shifts of the H atom. More... »

PAGES

1681-1688

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-012-0233-0

DOI

http://dx.doi.org/10.1007/s11172-012-0233-0

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https://app.dimensions.ai/details/publication/pub.1016120864


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