Kinetic studies of nucleophilic substitution reactions of dansyl, bansyl, dabsyl chlorides with pyridines have been investigated at $0^{circ}C$ in a range of methanol-acetonitrile binary solvent mixtures. The order of magnitude for reactivity of substrates with pyridines in the same reaction condition is dabsyl chloride>dansyl chloride> bansyl chloride. The value of $ ho$n(-2.29~ -4.66) and $eta$(0.537~0.901) associated with a change substituent in the nucleophile are large and indicate a relatively advanced bond formation in the transition state. Solvatochromic correlations were predicted the increase of bond formation transition state according to the increasing MeCN contents, showing the greater contribution of polarity polarizability ($pi$*) than hydro-gen bond donar acidity($alpha$). We conclude that the reactions of dansyl, bansyl, dabsyl chlorides with pyridines proceed via associative Sn2 type reaction mechanism.