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• W1983294512 startingPage "1919" @default.
• W1983294512 abstract "The reactions of the title substrate with a series of secondary alicyclic amines have been subjected to a kinetic study in water at 25°C, ionic strength 0.2 mol dm–3. Under amine excess pseudo-first-order rate coefficients (Kobs) are found throughout. The order in amine varies from 1–2 according to the amine basicity and the experimental conditions. A general reaction scheme with a zwitterionic and an anionic tetrahedral intermediate (1 and 2, respectively) accounts for the rate equations found. The pKa of 1 is estimated along with some microconstants in the scheme. From the values of the microconstants, either obtained experimentally or estimated, it is deduced that 1 is more stable than its analogue (3) formed in the aminolysis of S-phenyl thioacetate, and therefore, 1 has time for proton transfer to a base to yield 2. The rate coefficients for expulsion of an amine (pK–1) and PhS–(K2) from 1 are both smaller than those for expulsion from 3. The Brønsted plots for K1(rate coefficient for formation of 1), K1(=K1/K–1) and K–1 have slopes β= 0.2, 1.2 and –1.0, respectively. The pKa value of an (hypothetical)amine for which K–1=K2 is deduced: pKao= 10.3 ± 0.5, which is smaller than that derived from the aminolysis of S-phenyl thioacetate (pKao= 12.2)." @default.
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• W1983294512 date "1991-01-01" @default.
• W1983294512 modified "2023-10-16" @default.
• W1983294512 title "Kinetics and mechanism of the aminolysis of phenyl dithioacetate in aqueous solution" @default.
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• W1983294512 doi "https://doi.org/10.1039/p29910001919" @default.
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