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• W2004191704 abstract "A kinetic study is reported for reactions of 4-nitrophenyl benzoate (1c) and O-4-nitrophenyl X-substituted thionobenzoates (2a−e) with a series of pyridines in 80 mol % H2O/20 mol % dimethyl sulfoxide (DMSO) at 25.0 ± 0.1 °C. O-4-Nitrophenyl thionobenzoate (2c) is more reactive than its oxygen analogue 1c toward all the pyridines studied. The Brønsted-type plot is linear with βnuc = 1.06 for reactions of 1c but curved for the corresponding reactions of 2c with βnuc decreasing from 1.38 to 0.38 as the pyridine basicity increases, indicating that the reaction mechanism is also influenced on changing the electrophilic center from CO to CS. The curvature center of the curved Brønsted-type plots (defined as pKao) occurs at pKa = 9.3 regardless of the electronic nature of the substituent X in the nonleaving group. The Hammett plot for reactions of 2a−e with 4-aminopyridine is nonlinear, i.e., the substrates having an electron-donating substituent exhibit negative deviations from the Hammett plot. However, the Yukawa−Tsuno plot for the same reactions exhibits good linear correlation, indicating that the negative deviations shown by these substrates arise from stabilization of the ground state through resonance interaction between the electron-donating substituent X and the CS bond." @default.
• W2004191704 created "2016-06-24" @default.
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• W2004191704 date "2006-10-24" @default.
• W2004191704 modified "2023-10-03" @default.
• W2004191704 title "Modification of Both the Electrophilic Center and Substituents on the Nonleaving Group in Pyridinolysis of <i>O</i>-4-Nitrophenyl Benzoate and Thionobenzoates" @default.
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• W2004191704 doi "https://doi.org/10.1021/jo061682x" @default.
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