Theoretical studies of 5-exo selective intramolecular cyclization of o-alkynylbenzoic acid catalyzed by organic base

Masahiro Terada, Chikashi Kanazawa, Masahiro Yamanaka

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Theoretical studies of the organic base-catalyzed 5-exo intramolecular cyclization of o-alkynylbenzoic acid were documented. The acidic fragment participating in the transition states was shown to reduce the activation energy significantly on the basis of hybrid DFT (BHandHLYP) calculation of 5-exo and 6-endo transition states. Furthermore, preference for the 5-exo cyclization mode was rationalized by natural population analysis of optimized structures of the transition states and the reactants.

Original languageEnglish
Pages (from-to)819-825
Number of pages7
JournalHeterocycles
Volume74
Issue numberC
Publication statusPublished - 2007 Dec 31

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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