A theoretical study of substituted norcaradiene with some strong electron withdrawing groups at position 7

Ting Hua Tang, Calvin S.Q. Lew, Yun Ping Cui, Brian Capon, Imre G. Csizmadia

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The valence isomeric equilibria between cycloheptatriene and norcaradiene and, as well, their substituted derivatives at position 7 containing strong electron withdrawing groups (7-cyano, 7,7-dicyano and 7,7-difluoro substituted) were investigated computationally using ab initio methods and charge density topological analysis at the 6-31G*, 6-31G** and MP2/6-31G** levels of theory. The calculated relevant cross sections of the potential energy surface shows that the 7,7-dicyanonorcaradiene, in which the CN group acts as a σ- and π-acceptor, behaves as a stable neutral homoaromatic compound. As a comparison, the destabilized 7,7-difluoronorcaradiene, in which fluorine substituents act as a σ-acceptor and a π-donor, was studied also.

Original languageEnglish
Pages (from-to)149-164
Number of pages16
JournalJournal of Molecular Structure: THEOCHEM
Volume305
Issue numberC
DOIs
Publication statusPublished - Mar 10 1994

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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