Alkaline hydrolysis of N-methylazetidin-2-one. Hydration effects
1998
Abstract Semiempirical calculations (PM3) have been used to investigate the reaction mechanism (B AC2 ) of the alkaline hydrolysis of N -methylazetidin-2-one. This mechanism involves the nucleophilic attack of a hydroxyl ion on the carbonyl carbon to give a tetrahedral complex followed by cleavage of the CN bond and proton transfer to form the final product. The influence of the solvent in this process has been analyzed using the supermolecular approach with a water solvation sphere of 20 molecules around the solute. The results obtained have been compared with those based on a continuum treatment of the solvent with semiempirical and ab initio methodology. The potential barrier of 17.5 kcal mol −1 due to the attack of the nucleophile is very close to the experimental value (16.1 kcal mol −1 ) and the final product is about 52 and 27 kcal mol −1 more stable than the reactives and the tetrahedral intermediate, respectively.
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