AM1 calculations on a series of bicyclic azetidin-2-ones and bicyclic 1,3-diazetidin-2-ones: investigations towards putative β-lactamase inactivators

Abstract

In this study we have carried out AM1 calculations on a series of bicyclic azetidin-2-ones and bicyclic 1,3-diazetidin-2-ones to assess the thermochemical stability and electrophilicity of the carbonyl group. Theoretical investigations based on calculated heats of formation, Hf and atomic charges, q, predict that bicyclic diazetidinones are stable systems with a highly electrophilic carbonyl group. The results suggest that bicyclic 1,3-diazetidin-2-ones should be explored as a novel class of β-lactamase inactivators. © 1991.