Journal of the Chemical Society. Perkin transactions II p. 327 - 330 (1981)
Update date:2022-08-25
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Guanti, Giuseppe
Cevasco, Giorgio
Thea, Sergio
Dell'Erba, Carlo
Petrillo, Giovanni
The rate of release of p-nitrophenol in the reaction of nine substituted phenolates with p-nitrophenyl acetate has been determined by spectrophotometric measurements in absolute ethanol at 22 deg C.The phenolate anion is the reactive species and competes with ethoxide anion, arising from solvolysis of the phenolate, for nucleophilic attack on the ester carbonyl carbon atoms.From the observed reaction rates the solvolysis constants and the pKa values of the phenols were obtained.The second-order rate constants for phenoxide anions were correlated with the pKa values of the corresponding phenols giving a Broensted β value of 0.57.A comparison with the nucleophilic reactivity of arenethiolates towards the same substrate in ethanol has been made.The rate-determining step is probably the expulsion of the leaving group in the raection of arenethiolates, whereas it is the nucleophile attack in the reaction of phenoxides.
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