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is more reactive than the dissociated EtO – . Hammett plots for the reactions of 7a-i with the dissociated EtO – and ion-paired EtOK exhibit excellent linear correlations with X = 3.00 and 2.47, respectively. The reactions have been suggested to proceed through a stepwise mechanism in which departure of the leaving-group occurs after the RDS. The correlation of the kEtOK/kEtO ratio with the X constants exhibits excellent linearity with a slope of –0.53. It is concluded that the ion-paired EtOK catalyzes the reaction by increasing the electrophilicity of the reaction center rather than by enhancing the nucleofugality of the leaving group.

bulletin of the korean chemical society

Kinetic Study on Nucleophilic Substitution Reactions of 4-Nitrophenyl X-Substituted-Benzoates with Potassium Ethoxide: Reaction Mechanism and Role of K<sup>+</sup>Ion

Kinetic Study on Nucleophilic Substitution Reactions of 4-Nitrophenyl X-Substituted-Benzoates with Potassium Ethoxide: Reaction Mechanism and Role of K+Ion

Kinetic Study on Nucleophilic Substitution Reactions of 4-Nitrophenyl X-Substituted-Benzoates with Potassium Ethoxide: Reaction Mechanism and Role of K⁺Ion