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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 6, Number 3
March 20, 1985 

Nucleophilic Substitution Reaction of Dansyl Chloride with Substituted Anilines
Sung Bin Han, Dae Dong Sung, Ikchoon Lee
Nucleophilic substitution reaction of dansyl chloride with anilines in various solvents have been investigated. The Brønsted β and Hammett ρ 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 (π *) compared to hydrogen bond donor acidity (α). The effect of solvent on rate was found to violate the reactivity-selectivity principle.
162 - 164
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