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

Conformational potential energy surfaces were generated using the semiempir ical AM1 method for selected alpha-substituted arylpropanoids. The global m inima were subjected to full AMI geometry optimizations. Keto-enol tautomer ization energies were also computed at the AMI level. The results obtained were compared to those of Simple Huckel Molecular Orbital calculations. Ant ifungal activities of the compounds studied were reported as minimal inhibi tory concentration values. These values were correlated with computed molec ular parameters. A set of alpha-substituted acetophenones (using Me, F and Cl as substituents) were also studied, as model compounds for the antifunga ls, at the AMI and the RHF/STO-3G levels of theory. The enolization energie s were calculated at both levels of theory. (C) 1999 Elsevier Science B.V. All rights reserved.