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• W2024025197 endingPage "1726" @default.
• W2024025197 startingPage "1722" @default.
• W2024025197 abstract "A kinetic study on nucleophilic substitution reactions of phenyl Y-substituted-phenyl carbonates (5a-5j) with ethylamine in 80 mol % <TEX>$H_2O$</TEX>/20 mol % DMSO at <TEX>$25.0{pm}0.1^{circ}C$</TEX> is reported. The plots of <TEX>$k_{obsd}$</TEX> vs. [amine] are linear for the reactions of substrates possessing a strong electron-withdrawing group (EWG) but curve upward for those of substrates bearing a weak EWG, indicating that the electronic nature of the substituent Y in the leaving group governs the reaction mechanism. The reactions have been concluded to proceed through a stepwise mechanism with one or two intermediates (a zwitterionic tetrahedral intermediate <TEX>$T^{pm}$</TEX> and its deprotonated form <TEX>$T^-$</TEX>) depending on the nature of the substituent Y. Analysis of Bronsted-type plots and dissection of <TEX>$k_{obsd}$</TEX> into microscopic rate constants have revealed that the reactions of substrates possessing a strong EWG (e.g., 5a-5f) proceed through <TEX>$T^{pm}$</TEX> with its formation being the rate-determining step, while those of substrates bearing a weak EWG (e.g., 5g-5j) proceed through <TEX>$T^{pm}$</TEX> and <TEX>$T^-$</TEX>." @default.
• W2024025197 created "2016-06-24" @default.
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• W2024025197 date "2013-06-20" @default.
• W2024025197 modified "2023-09-28" @default.
• W2024025197 title "A Kinetic Study on Ethylaminolysis of Phenyl Y-Substituted-Phenyl Carbonates: Effect of Leaving-Group Substituents on Reactivity and Reaction Mechanism" @default.
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• W2024025197 doi "https://doi.org/10.5012/bkcs.2013.34.6.1722" @default.
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