Study of the Alkaline Hydrolysis of the Azetidin-2-one Ring by ab initio Methods: Influence of the solvent |
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Authors: | Juan Frau Josefa Donoso Francisco Muoz Bartolom Vilanova Francisco García-Blanco |
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Institution: | Juan Frau,Josefa Donoso,Francisco Muñoz,Bartolomé Vilanova,Francisco García-Blanco |
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Abstract: | A comprehensive study of the alkaline hydrolysis of the β-lactam ring of azetidin-2-one was carried out using ab initio molecular-orbital calculations at the RHF/6-31 + G* level. The influence of the solvent on this reaction was investigated by using the reaction field method (SCRF); the solvent was found to suppress the interference of some gas-phase reactions and allow the presence of a transition state to be detected as the nucleophile approaches the β-lactam ring. The transition state corresponds to a structure where the OH? group lies at a distance of 1.927 Å from the C?O group of the β-lactam ring and exhibits a potential barrier of 13.6 kcal/mol. |
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