Pyridinolysis of Substituted Benzyl Benzenesulfonate in Acetonitrile

초록

Kinetic studies on the nucleophilic substitution reactions of Y-benzyl Z-benzenesulfonates with X-pyridines have been carring out in acetonitrile at 55.0 C. Hammett ρx, ρy, ρz values, Brönsted β values have been determined in order to clarify the transition state variations caused by changes in nuclophiles and leaving group and solvents. It was found that reaction proceeds via a dissociative Sn2 mechamism with a more product-like transition state compared to that for substrate with a less electron attractiong substituent.