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- W609775632 abstract "The kinetic studies of the reactions of <TEX>$alpha$</TEX>-chloroacetanilides <TEX>$(YC_6H_4NRC(=O)CH_2Cl;;R=H;(4);and;CH_3$</TEX> (5)) with pyridines have been carried out in dimethyl sulfoxide at 95 <TEX>${^{circ}C}$</TEX>. The pyridinolysis rates are faster with 4 than with 5 whereas the aminolysis rates with benzylamines are faster with 5 than with 4. The Brønsted <TEX>${beta}_X$</TEX> values are in the range from 0.30 to 0.32 and the cross-interaction constants, <TEX>$rho_{XY}$</TEX>, are small negative values; <TEX>$rho_{XY}$</TEX> = -0.06 and -0.10 for 4 and 5, respectively. Based on these and other results, the pyridinolyses of <TEX>$alpha$</TEX>-chloroacetanilides are proposed to proceed via a stepwise mechanism with rate-limiting addition of the nucleophile to the carbonyl group to form zwitterionic tetrahedral intermediate (<TEX>$T^{pm}$</TEX>) followed by a bridged type transition state to expel the leaving group." @default.
- W609775632 created "2016-06-24" @default.
- W609775632 date "2005-05-20" @default.
- W609775632 modified "2023-10-03" @default.
- W609775632 title "Nucleophilic Substitution Reactions of α-Chloroacetanilides with Pyridines in Dimethyl Sulfoxide" @default.
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