From pentalene to dicyclopenta[b,g]naphthalene, or the change towards delocalized structures

Chemphyschem. 2006 Jan 16;7(1):240-4. doi: 10.1002/cphc.200500327.

Abstract

Using triples-corrected coupled-cluster methods as well as other high-level theoretical approximations, the optimized parameters and isomerization barriers of the family of compounds cyclopentadiene-(benzene)x-cyclopentadiene (x = 0, 1, 2) are computed. In contrast to previous studies, s-indacene presents a localized C(2h) geometry. Also, the localized structure of pentalene is found to be the most stable, but when two benzene rings are intercalated between the five-member rings of pentalene, the resulting molecule preferably adopts a delocalized D(2h) conformation.