14503-42-5Relevant articles and documents
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 S(N)2 reactions between m-chlorobenzyl para- substituted benzenesulfonates and cyanide ion
Westaway, Kenneth C.,Fang, Yao-Ren,Persson, Jonas,Matsson, Olle
, p. 3340 - 3344 (2007/10/03)
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 S(N)2 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 shorter nucleophile-α-carbon bond and a longer α- carbon-leaving group bond. The changes in transition state structure are consistent with the Bond Strength Hypothesis.