Nitrogen-15 Kinetic Isotope Effects in the Menschutkin-Type Reaction of Benzyl Benzenesulfonates with N,N-Dimethylanilines |
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| Authors: | Takashi Ando Hiroshi Yamataka Eitaro Wada |
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| Affiliation: | 1. Department of Chemistry, Shiga University of Medical Science, Otsu, Shiga 520–21, Japan;2. The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka 567, Japan;3. Mitsubishi-Kasei Institute of Life Sciences, Machida, Tokyo 194, Japan |
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| Abstract: | Nitrogen-15 kinetic isotope effects were measured for the Menschutkin-type reaction of Z-substituted benzyl X-substituted benzenesulfonates with Y-substituted N,N-dimethylanilines (Eq. 1) in acetone at 35°C. The values of 14k/15k for six combinations of X, Y, and Z fell in the range of 1.002–1.004. These small and almost constant nitrogen isotope effects are in contrast to the large and extensively varying carbon-14 and small but distinctly changing α-tritium isotope effects observed for this reaction series. The results are discussed in connection with the reactivity–selectivity relationships. |
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