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Delocalizations in sigma-radical cations: the intriguing structures of ionized [n]rotanes
Andrey A Fokin1, Peter R Schreiner, Sergei I Kozhushkov
1Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine. aaf@xtf.ntu-kpi.kiev.ua
Organic Letters
|February 28, 2003
Abstract:
Highly symmetric aliphatic hydrocarbons such as D(4h)-[4]rotane do not necessarily have degenerate HOMOs. According to our predictions based on high-level computations, its radical cation should display a highly delocalized D(4h)-symmetric structure, in contrast to its Jahn-Teller distorted cousin, the radical cation of [3]rotane, which exists in two distonic localized forms with C(2v) and C(s) symmetry.