Enthalpy-entropy correlations in reactions of 2,4-dinitrophenyl benzoate with phenols in the presence of potassium hydrogen carbonate and with potassium phenoxides in dimethylformamide

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Abstract
Temperature dependences of the relative reactivity of substituted phenols RC6H4OH in the presence of potassium hydrogen carbonate and of potassium phenoxides RC6H4O−K+ toward 2,4-dinitrophenyl benzoate in dimethylformamide were studied using the competitive reactions technique. Correlation analysis of the relative rate constants k R/k H and differences in the activation parameters (ΔΔH ≠ and ΔΔS ≠) of competitive reactions revealed the existence of two isokinetic series for each type of nucleophiles. The mechanism of transesterification was interpreted in terms of an approach based on analysis of the effect of substituent in the nucleophile on the activation parameters.

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