Nucleophilic substitution reaction of dansyl chloride with anilines in various solvents have been investigated. The Bronsted ${eta}$ and Hammett ${ ho}_N$ values indicated that the bond formation is advanced more than the bond breaking at the transition state. Solvatochromic correlations also predicted the importance of bond formation at the TS, showing a greater contribution of polarity (${pi}^{ast}$) compared to hydrogen bond donor acidity (${alpha}$). The effect of solvent on rate was found to violate the reactivity-selectivity principle.