Bulletin of the Korean Chemical Society

  • 제6권3호
  • /
  • Pages.162-164
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  • 1985
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Nucleophilic Substitution Reaction of Dansyl Chloride with Substituted Anilines$^1$

  • 발행 : 1985.06.20
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초록

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.

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참고문헌

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피인용 문헌

  1. Kinetics and mechanism of the pyridinolysis of benzenesulfonyl chlorides in methanol vol.12, pp.6, 1985, https://doi.org/10.1002/(sici)1099-1395(199906)12:6<425::aid-poc147>3.0.co;2-3