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- W2021000818 abstract "The effect of α- and β-cyclodextrins on the cleavage of the thiocarboxylic S-esters, S-p-nitrophenyl thioacetate (1) and S-ethyl p-nitrothiobenzoate (3), was compared with their effect on the cleavage of the corresponding oxygen esters, p-nitrophenyl acetate (2) and ethyl p-nitrobenzoate (4). The rate constants of α- or β-cyclodextrin-accelerated cleavage of 1 (1.5×10−2 or 4.8×10−2 s−1 at pH 10.5, 25 °C) were almost identical with the values of 2 (1.6×10−2 or 4.2×10−2 s−1), definitely showing the rate-determining formation of tetrahedral intermediates. The cleavage of 3 was accelerated by α- and β-cyclodextrins, whereas the cleavage of 4 was decelerated by β-cyclodextrin but was not affected by α-cyclodextrin. The contrast in the effect of cyclodextrins on 3 and 4 was ascribed to the difference of the rate of breakdown of the tetrahedral intermediates to products, caused by different pK’s of the leaving groups of 3 (10.5) and 4 (16.0). The formation of tetrahedral intermediates confirmed in the cyclodextr..." @default.
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- W2021000818 date "1980-04-01" @default.
- W2021000818 modified "2023-09-23" @default.
- W2021000818 title "The Cyclodextrin-accelerated Cleavage of Thiocarboxylic<i>S</i>-Esters" @default.
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- W2021000818 doi "https://doi.org/10.1246/bcsj.53.1073" @default.
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