1969 Volume 42 Issue 10 Pages 2894-2898
The reaction of p-nitrophenyl benzenesulfonates has been investigated in dioxane-water solvent. The overall rate constant, kA, was separated into two composite rate constants, kAr, and kSO2, corresponding to the cleavage of C–O and S–O bonds respectively. The reactivities of hydroxide and thiophenoxide in this reaction were compared. The overall rate constant was found to be several times larger with OH− than with PhS−. The reactivity of OH− was largely due to its higher reactivity toward sulfur, while its reactivity toward carbon atom was comparable to that of PhS−. Substituent effect of the nucleophile, thiophenoxide and of the substrate shed some light on the mechanism of this reaction.
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