A quantum chemical study of the C6H5+ potential energy surface. Evidence for a nonclassical pyramidal carbenic species

W.A.M. Castenmiller, H.M. Buck

Research output: Contribution to journalArticleAcademicpeer-review

25 Citations (Scopus)

Abstract

MINDO/3 and STO-3G MO calculations including geometry optimization have been performed for nonlinear C6H+5 structures. The phenyl cation 5 is the lowest energy compound on the surface, followed by the nonclassical pyramidal carbenic structure 4. Other local minima include the bicyclic carbene 6 and the benzvalenyl cation 7. Fairly good agreement between the results from both methods was obtained. The electronic structure of 4 is explained using orbital interaction diagrams which show the stabilization of the cyclopentadienyl cation by the apical carbon atom and the relation between 4 and pyramidal transition-metal complexes. The electronic structure of 6 is related to that of the bicyclo[3.1.0]hexenyl cation 12. Activation energies for rearrangement reactions on the energy surface show that 4 can probably be studied starting from benzvalene-type precursors.
Original languageEnglish
Pages (from-to)207-213
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume96
Issue number7-8
DOIs
Publication statusPublished - 1977

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