Bulletin of the Korean Chemical Society

  • 제32권3호
  • /
  • Pages.1071-1073
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  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Aminolysis of 4-Nitrobenzenesulfenyl Chloride

  • Lee, Jong-Pal (Department of Chemistry, Dong-A University) ;
  • Lee, Sung-Sik (Department of Chemical Engneering, Dong-A University) ;
  • Koo, In-Sun (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University)
  • 투고 : 2010.12.03
  • 심사 : 2011.01.08
  • 발행 : 2011.03.20
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초록

The reactions of 4-nitrobenzenesulfenyl chloride with substituted benzylamines proceed through three pathways, the uncatalyzed ($k_2$) and catalyzed ($k_3$) paths including solvolysis ($k_o$) by the solvent. The large value of primary normal kinetic isotope effects imply that the proton transfer occurs concurrently from benzylamine to Cl atom of the substrate. The ${\beta}_x$ and ${\rho}_x$ values for the catalyzed path, $k_3$, are greater than those for the uncatalyzed path, indicating that greater degree of bond formation in the catalyzed TS compared to the uncatalyzed TS.

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