Equilibration of N-(2-cyanoethyl) pyridinium cations with substituted pyridines and acrylonitrile. A change in rate-determining step in an E1cb reaction

JW Bunting, A Toth, CKM Heo…

Index: Bunting, John W.; Toth, Andrea; Heo, Christina K. M.; Moors, Rodney G. Journal of the American Chemical Society, 1990 , vol. 112, # 24 p. 8878 - 8885

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Citation Number: 29

Abstract

Abstract: The rates of equilibration of N-(2-cyanoethyl) pyridinium cations (1) with the corresponding pyridines and acrylonitrile have been measured in aqueous solutions of ionic strength 0.1 at 25 OC. Second-order rate constants (koH) have been obtained for the hydroxide ion catalyzed elimination reactions of 16 ring-substituted 1 having pyridine leaving groups of pKB, in the range 1.5-9.7. Br~ nsted plots of log koH vs PKBH are" ...