Exploratory molecular orbital calculations on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds

A. M. Rodríguez, F. A. Giannini, H. A. Baldoni, F. D. Suvire, S. Zacchino, R. D. Enriz, P. Csaszar, I. G. Csizmadia

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected α-substituted arylpropanoids. The global minima were subjected to full AM1 geometry optimizations, Keto-enol tautomerization energies were also computed at the AM1 level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Antifungal activities of the compounds studied were reported as minimal inhibitory concentration values. These values were correlated with computed molecular parameters. A set of α-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifungals, at the AM1 and the RHF/STO-3G levels of theory. The enolization energies were calculated at both levels of theory.

Original languageEnglish
Pages (from-to)283-303
Number of pages21
JournalJournal of Molecular Structure: THEOCHEM
Volume463
Issue number3
DOIs
Publication statusPublished - May 3 1999

Keywords

  • Antifungal activity
  • Conformational analysis
  • Keto-enol tautomerization
  • Potential energy surfaces
  • Semiempirical and ab initio computations
  • α-substituted acetophenones

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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