Kinetic isotope effects in the Menshutkin-type reaction of benzyl benzenesulfonates with N, N-dimethylanilines. Variation in the transition-state structure

T Ando, H Tanabe, H Yamataka

Index: Ando, Takashi; Tanabe, Hiroshi; Yamataka, Hiroshi Journal of the American Chemical Society, 1984 , vol. 106, # 7 p. 2084 - 2088

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Citation Number: 38

Abstract

Abstract: Primary carbon-14 and secondary a-tritium isotope effects were measured for the Menschutkin-type reaction of m-bromobenzyl-methylene-'4C X-substituted benzenesulfonates with Y-substituted N, N-dimethylanilines in acetone at 35 OC (eq 1; Z= m- Br). The large carbon-14 (I2k/l4k= 1.117-1.151) and small a-tritium (Hk/Tk= 1.026-1.041) isotope effects were consistent with the SN2 mechanism of the reaction. A monotonous ...