Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Kinetics and Mechanism for the Reactions of N-Methyl-N-phenylcarbamoyl Chlorides with Benzylamines in Acetonitrile

  • Published : 1996.08.20
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Abstract

Kinetic studies are carried out on the reactions of N-methyl-N-phenylcarbamoyl chlorides with benzylamines in acetonitrile. The selectivity parameters, ρX (=-0.6~-0.8), ρY (=1.0-1.1), and ρXY (=-0.14), suggest that the reaction proceeds by an SN2 mechanism. Kinetic isotope effects, kH/kD, involving deuterated nucleophiles (XC6H4CH2ND2) are all inverse type (<1.0), and the trends of changes in the magnitude are consistent with those expected for the observed negative sign of ρXY(=∂ρX/∂σY = ∂ρY/∂σX < 0). The relatively low activation enthalpies also support the proposed mechanism.

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