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

A.M RODRIGUEZ; F. GIANNINI,; H. BALDONI; F.SUVIRE; S.ZACCHINO; ENRIZ R.D.; PAL CSASZAR; I.G. CSIZMADIA

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 1999 vol. 463 p. 283 - 303

0166-1280

Conformational potential energy surfaces were generated using the semiempirical AM1 method for selected a-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 Hu¨ckel 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 a-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.