Using 11C/14C Incoming Group and Secondary α-Deuterium KIEs To Determine How a Change in Leaving Group Alters the Structure of the Transition State of the …

KC Westaway, Y Fang, J Persson…

Index: Westaway, Kenneth C.; Fang, Yao-Ren; Persson, Jonas; Matsson, Olle Journal of the American Chemical Society, 1998 , vol. 120, # 14 p. 3340 - 3344

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Citation Number: 28

Abstract

The 11C/14C incoming group and secondary α-deuterium KIEs and Hammett ρ value found by changing the substituent in the leaving group of the SN2 reactions between meta- chlorobenzyl para-substituted benzenesulfonates and cyanide ion in 0.5% aqueous acetonitrile at 0° C suggest that these reactions occur via an unsymmetrical, product-like transition state. Changing to a better leaving group leads to a transition state with a slightly ...