• Bulletin of the Korean Chemical Society
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• v.32 no.3
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• pp.1071-1073
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• 2011

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.