A Kinetic Study on Nucleophilic Displacement Reactions of Aryl Benzenesulfonates with Potassium Ethoxide: Role of K+ Ion and Reaction Mechanism Deduced from …

IH Um, JS Kang, YH Shin, E Buncel

Index: Um, Ik-Hwan; Kang, Ji-Sun; Shin, Young-Hee; Buncel, Erwin Journal of Organic Chemistry, 2013 , vol. 78, # 2 p. 490 - 497

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Citation Number: 26

Abstract

Pseudofirst-order rate constants (k obsd) have been measured spectrophotometrically for the nucleophilic substitution reactions of 2, 4-dinitrophenyl X-substituted benzenesulfonates 4a–f and Y-substituted phenyl benzenesulfonates 5a–k with EtOK in anhydrous ethanol. Dissection of k obsd into k EtO–and k EtOK (ie, the second-order rate constants for the reactions with the dissociated EtO–and ion-paired EtOK, respectively) shows that the ion- ...