SN1-SN2 and SN2-SN3 mechanistic changes revealed by transition states of the hydrolyses of benzyl chlorides and benzenesulfonyl chlorides

• Published in: Journal of Computational Chemistry Vol. 35; no. 15; pp. 1140 - 1148
• Main Authors: Yamabe, Shinichi, Zeng, Guixiang, Guan, Wei, Sakaki, Shigeyoshi
• Format: Journal Article
• Language: English; Japanese
• Published: Blackwell Publishing Ltd 05.05.2014; Wiley
• Subjects: benzenesulfonyl and benzyl chlorides; hydrolysis; nucleophilic substitutions; SN1-SN2; SN2-SN3; theoretical calculation

Hydrolysis reactions of benzyl chlorides and benzenesulfonyl chlorides were theoretically investigated with the density functional theory method, where the water molecules are explicitly considered. For the hydrolysis of benzyl chlorides (para‐ZC6H4CH2Cl), the number of water molecules (n) slight...