Abstract
AbstractThe kinetics of nucleophilic bimolecular substitution reactions of γ‐functionalized allyl bromides with non‐substituted and p‐substituted sodium arenesulfinates has been studied. Both the structure of allyl bromides and nucleophilicity of arenesulfinate ions exerted a significant effect on the values of the kinetic parameters such as the second‐order rate constants k, activation energy EA, and changes in the entropy ΔS≠, enthalpy ΔH≠, and free energy ΔG≠ of the formation of the activated complex from reactants. Based on the evaluation of kinetic parameters, the reactants could be arranged, according to their decreasing reactivity in the SN2‐reactions as follows: p‐toluenesulfinate ion > benzenesulfinate ion > p‐chlorobenzenesulfinate ion and 4‐bromo‐2‐butenenitrile > 1,3‐ dibromopropene, respectively. Comparison was also made between the kinetic data obtained and some delocalization reactivity indexes for both the substrates and nucleophiles. The enthalpy–entropy compensation effect was observed for the reactions of sodium arenesulfinates with γ‐functionalized allyl bromides. Copyright © 2009 John Wiley & Sons, Ltd.
Published Version
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