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• W2322348148 endingPage "7031" @default.
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• W2322348148 abstract "A kinetic study is reported for SNAr reactions of 1-(Y-substituted-phenoxy)-2,4-dinitrobenzenes (1a–1h) with amines in MeCN. The plots of pseudo-first-order rate constant versus amine concentration curve upward, indicating that the reactions are catalyzed by a second amine molecule. The Brønsted-type plots for the reaction of 1-(4-nitrophenyl)-2,4-dinitrobenzene (1a) with secondary amines are linear with βnuc = 1.10 and 0.85 for the uncatalyzed and catalyzed reactions, respectively, while the Yukawa–Tsuno plots for the reactions of 1a–1h with piperidine result in excellent linear correlations with ρY = 1.85 and r = 0.27 for the uncatalyzed reaction and ρY = 0.73 and r = 0.23 for the catalyzed reaction. The catalytic effect decreases with increasing amine basicity or electron-withdrawing ability of the substituent Y in the leaving group. Activation parameters calculated from the rate constants measured at five different temperatures for the catalyzed reaction of 1a with piperidine are ΔH‡ = 0.38 kcal/mol and ΔS‡ = −55.4 cal/(mol K). The catalyzed reaction from a Meisenheimer complex (MC±) is proposed to proceed through a concerted mechanism with a cyclic transition-state rather than via a stepwise pathway with an anionic intermediate, MC–. Deuterium kinetic isotope effects provide further insight into the nature of the concerted transition state." @default.
• W2322348148 created "2016-06-24" @default.
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• W2322348148 date "2014-07-15" @default.
• W2322348148 modified "2023-09-30" @default.
• W2322348148 title "Kinetic Study on S_NAr Reaction of 1-(Y-Substituted-phenoxy)-2,4-dinitrobenzenes with Cyclic Secondary Amines in Acetonitrile: Evidence for Cyclic Transition-State Structure" @default.
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• W2322348148 doi "https://doi.org/10.1021/jo5011872" @default.
• W2322348148 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25004104" @default.
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