Theoretical studies on neutral hydrolysis of N-benzyl 3-oxo-β-sultam

The hydrolysis of N-benzyl 3-oxo-β-sultam and the general base catalysis by the neucleophile are investigated. Different possible mechanistic pathways of the reaction are proposed. Both B3LYP/6-31G* and B3LYP/6-311+G* were employed to calculate the reaction pathways. The results show that in the case of non-catalyzed hydrolysis the pathways producing N-benzyl-acylamide methyl sulfonate (P1) and N-benzyl-2-sulfonic acylamide acetic acid (P2) have very similar activation energies; they are competing reactions. However, in the case of catalyzed hydrolysis by a second water molecule, the break of C-N bond is preferred. The theoretical results are in good agreement with the recent experimental observations.