Water-assisited alkaline hydrolysis of monobadtams:a theoretical study

摘要

A theoreticalstudy of the water-assisted alkaline hydrolysis of 2-azetidinone,3-formylamino-2-azetidinone and 3-formylamino-2-azetidine-1-sulfonate ion is carried out at the B3LYP/6-31+G level.The effect of bulk solvent is taken into account using the PCM solvation model while specific solvent effects are represented calculated free energy barriers in solution are in reasonable agreement with experimental values.The observed subsitiuent effects due to the presence of the 3-formylamino and the SO_3 groups attached to the #beta#-lactam ring are crucial factors determining the hydrolysis of monobactam antibiotics.