Manojkumar, TK Suh, SB Oh, KS Cho, SJ Cui, CZ Zhang, X Kim, KS 2024-01-21T05:08:45Z 2024-01-21T05:08:45Z 2021-09-01 2005-04-01 0022-3263 https://pubs.kist.re.kr/handle/201004/136557 We present an ab initio study of the acid-promoted hydrolysis reaction mechanism of N-formylaziridine in comparison with formamide. Since the rate of amide hydrolysis reactions depends on the formation of the tetrahedral intermediate, we focused our attention mainly on the reactant complex, the tetrahedral intermediate, and the transition state connecting these two stationary points. Geometries were optimized using the density functional theory, and the energetics were refined using ab initio theory including electron correlation. Solvent effects were investigated by using polarizable continuum method calculations. The proton-transfer reaction between the O-protonated and N-protonated amides was investigated. In acidic media, despite that the N-protonated species is more stable than the O-protonated one, it is predicted that both N-protonated and O-protonated pathways compete in the hydrolysis reaction of N-formylaziridine. English AMER CHEMICAL SOC CATALYZED AMIDE HYDROLYSIS AB-INITIO AQUEOUS-SOLUTION ALKALINE-HYDROLYSIS HYDROGEN-BONDS N-(O-CARBOXYBENZOYL)-L-AMINO ACID ENZYMATIC CATALYSIS MOLECULAR-STRUCTURE DISTORTED AMIDES SERINE PROTEASES Theoretical studies on the mechanism of acid-promoted hydrolysis of N-formylaziridine in comparison with formamide Article 10.1021/jo0493323 1 JOURNAL OF ORGANIC CHEMISTRY, v.70, no.7, pp.2651 - 2659 JOURNAL OF ORGANIC CHEMISTRY 70 7 2651 2659 scie scopus 000227928200030 2-s2.0-17044408389 Chemistry, Organic Chemistry Article CATALYZED AMIDE HYDROLYSIS AB-INITIO AQUEOUS-SOLUTION ALKALINE-HYDROLYSIS HYDROGEN-BONDS N-(O-CARBOXYBENZOYL)-L-AMINO ACID ENZYMATIC CATALYSIS MOLECULAR-STRUCTURE DISTORTED AMIDES SERINE PROTEASES Mechanism N-formylaziridine hydrolysis