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Reactivity of sodium arenesulfinates in the substitution reaction to γ-functionalized allyl bromides
Khamis, Galina,Stoeva, Stoyanka,Aleksiev, Dimitar
, p. 461 - 467 (2011/08/06)
The 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
