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Nucleophilic Substitution Reaction of Dansyl Chloride with Substituted Anilines$^1$

  • Published : 1985.06.20

Abstract

Nucleophilic substitution reaction of dansyl chloride with anilines in various solvents have been investigated. The Bronsted ${\beta}$ and Hammett ${\rho}_N$ 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.

Keywords

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