Structure-reactivity correlations in the dissociative hydrolysis of 2′,4′-dinitrophenyl 4-hydroxy-X-benzenesulfonates
The hydrolysis reactions of several title esters in water at 60°C follow the rate law kobs = (ka + kb[OH-])/(1 + αH/Ka), where Ka is the ionization constant of the hydroxy group of the ester and kb is the second-order rate constant for the SN2(S) attack of hydroxide ion on the ionized ester. Hammett and Br?nsted correlations are consistent with a previous proposal that the mechanism related to ka is dissociative. An unusual relationship between ka values and redox equilibrium constants for substituted quinones is found to hold: this finding further supports the dissociative nature of the pathway related to ka.
Cevasco, Giorgio,Thea, Sergio
p. 6814 - 6817
(2007/10/03)
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