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- W1643344034 abstract "Kinetic studies of the reaction of O-methyl-S-phenylthiocarbonates with benzylamines in methanol at 45.0 ℃ have been carried out. The reaction proceeds by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, <TEX>$T^{pm}$</TEX>, with a hydrogen-bonded four-center type transition state (TS). These mechanistic conclusions are drawn based on (ⅰ) the large magnitude of <TEX>${rho}_X;and;{rho}_Z$</TEX>, (ⅱ) the normal kinetic isotope effects <TEX>$(k_H/k_D;>;1.0)$</TEX> involving deuterated benzylamine nucleophiles, (ⅲ) the positive sign of <TEX>${rho}_{XZ}$</TEX> and the larger magnitude of <TEX>${rho}_{XZ}$</TEX> than that for normal <TEX>$S_N2$</TEX> processes, and lastly (ⅳ) adherence to the reactivity-selectivity principle (RSP) in all cases." @default.
- W1643344034 created "2016-06-24" @default.
- W1643344034 date "2003-01-20" @default.
- W1643344034 modified "2023-09-30" @default.
- W1643344034 title "Kinetics and Mechanism of the Aminolysis of O-Methyl-S-Phenylthiocarbonates in Methanol" @default.
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- W1643344034 doi "https://doi.org/10.5012/bkcs.2003.24.1.091" @default.
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