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- W2036761750 abstract "The kinetics of the hydrolysis of p-nitrophenyl esters of straight chain carboxylic acids with various chain lengths, viz., acetate (C 2), octanoate (C 8) dodecanoate (C 12) and hexadecanoate (C 16) was investigated in ten aquiorgano binary solvent systems. In the Φ = 0.50 (50% v/v) solvent mixtures, aggregation and coiling-up of C 16 occur only in HOCH2CH2OH-H2O and Me2SOH2O, in which kC8/kC16 >> 1, whereas the hydrolytic behaviors of C 16 and C 8 are similar in all other solvents. But at Φ =0.30, C 16 aggregates and coils-up in all solvent mixtures except the t-BuOH-H2O system. If the kC8/kC16 values in the Φ =0.30 media are taken as an arbitrary standard, the order of decreasing hydrophobic-lipophilic interactions between the solvent and substrate molecules for the various solvents are as follows : HOCH2CH2OH > Me2SO > CH3OCH2CH2OH > DMF ˜ CH2OCH2CH2OCH3 > dioxane > ethanol ˜ acetone ˜ acetonitrile > t-BuOH. When kC8/kC16 >> 1, there is a large difference in the activation parameters between C 16 and its shorter counterparts. No simple correlation can be found between log (kC8/kC16) and various solvent polarity parameters, but log (kC8/kC16) correlates with Rekker's hydrophobic fragmental constants (f) of the organic components of these solvent systems (r = 0.976), indicating that the major factor which controls the hydrolysis of long-chain esters here is the hydrophobic-lipophilic interactions. Apparently, this is the first example of an application of Rekker's f constants to a correlation between solvent property and chemical reactivity in terms of rate constants." @default.
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- W2036761750 date "1985-06-01" @default.
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- W2036761750 title "The effects of hydrophobic-lipophilic interactions on chemical reactivity: 2. Solvent effects on the aggregation and self-coiling of long-chain molecules" @default.
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- W2036761750 doi "https://doi.org/10.1002/cjoc.19850030205" @default.
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