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• W2016125135 abstract "The reactions of secondary alicyclic amines with 2,4,6-trinitrophenyl methyl carbonate (TNPMC) and 2,4,6-trinitrophenyl acetate (TNPA) are subjected to a kinetic study in aqueous solution, 25.0 °C, ionic strength 0.2 (KCl). The reactions are studied by following spectrophotometrically (360 nm) the release of the 2,4,6-trinitrophenoxide anion. Under amine excess, pseudo-first-order rate coefficients (kobsd) are found. Plots of kobsd vs [amine] are linear, with the slope (kN) independent of pH. The Brönsted-type plots (log kN vs pKa of the conjugate acid of the amines) are linear, with slopes β = 0.41 and β = 0.36 for the reactions of TNPA and TNPMC, respectively. The predicted breaks of the Brönsted plots for stepwise mechanisms are pKa0 = 6.8 and 7.3, respectively. The lack of Brönsted breaks for these reactions and the values of the Brönsted slopes are consistent with concerted mechanisms. By comparison of the reactions under investigation among them and with similar aminolysis and pyridinolysis, the following conclusions can be drawn: (i) Secondary alicyclic amines react with TNPA and TNPMC by concerted mechanisms. (ii) TNPA is more reactive toward these amines than TNPMC due to the greater electron release of MeO from the latter substrate. (iii) The change of 2,4-dinitrophenoxy to 2,4,6-trinitrophenoxy in the zwitterionic tetrahedral intermediate (T±) formed in the reactions of the title amines with 2,4-dinitrophenyl acetate greatly destabilizes T±. (iv) Secondary alicyclic amines destabilize T± relative to pyridines. (v) The intermediate T± formed in the reactions of the title amines with S-(2,4,6-trinitrophenyl) acetate is greatly destabilized by substitution of S-(2,4,6-trinitrophenyl) by O-(2,4,6-trinitrophenyl) as the leaving group." @default.
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• W2016125135 title "Concerted Mechanisms of the Reactions of 2,4,6-Trinitrophenyl Methyl Carbonate and 2,4,6-Trinitrophenyl Acetate with Secondary Alicyclic Amines" @default.
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• W2016125135 doi "https://doi.org/10.1021/jo0100695" @default.
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