The kinetic studies of the reactions of $alpha$-chloroacetanilides $(YC_6H_4NRC(=O)CH_2Cl;;R=H;(4);and;CH_3$ (5)) with pyridines have been carried out in dimethyl sulfoxide at 95 ${^{circ}C}$. 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 ${eta}_X$ values are in the range from 0.30 to 0.32 and the cross-interaction constants, $ ho_{XY}$, are small negative values; $ ho_{XY}$ = -0.06 and -0.10 for 4 and 5, respectively. Based on these and other results, the pyridinolyses of $alpha$-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 ($T^{pm}$) followed by a bridged type transition state to expel the leaving group.