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Kinetic Isotope Effects in the Nucleophilic Substitution Reactions of Benzyl- and 1-Phenylethyl -benzenesulfonates with Deuterated Aniline Nucleophiles

  • Published : 1990.10.20

Abstract

Primary and secondary ${\alpha}$-deuterium kinetic isotope effects are determined with deuterated aniline nucleophiles in the nucleophilic substitution reactions of benzyl benzenesulfonates and 1-phenylethyl benzenesulfonates in acetonitrile at 30.0^{\circ}C. The $k_H/k_D$ values support our previous conclusions regarding the transition state structures proposed for the two reactions based on the cross-interaction constants ${\rho}_{ij}$; the former is a typical $S_N2$ reaction whereas in the latter the four-center transition state may be involved.

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  1. Cross-interaction constants as a measure of the transition state structure. Part 15. Kinetic isotope effects in the SN2 reactions of 2-phenylethyl derivatives with deuterated aniline nucleophiles vol.4, pp.2, 1991, https://doi.org/10.1002/poc.610040206
  2. Kinetics and Mechanism of the Aminolysis of Aryl N-Ethyl Thiocarbamates in Acetonitrile vol.69, pp.26, 1990, https://doi.org/10.1021/jo0484676
  3. Kinetics and Mechanism of the Addition of Benzylamines to Benzylidene-3,5-heptadione in Acetonitrile vol.70, pp.8, 1990, https://doi.org/10.1021/jo047832q