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■ Substituent Effects in Frontier Orbitals of Cyclic Hydroxamic Acids

Boris Weiss-López* and Héctor R. Bravo

*Departamento de Química, Facultad de Ciencias, Unversidad de Chile, Casilla 653, Santiago, Chile

Abstract

AM1 full geometry optimization of seven substituted cyclic hydroxamic acids (Hx) was performed. A qualitative correlation between E_lumo vs Hammett’s σ_p was observed. The reactivity of these 7-substituted Hx with hard nucleophiles seems to follow basic principles of frontier orbitals theory. Experimental support was obtained from the reaction of six Hx with 2-methoxyethylamine.