Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Influence of Pressure on the Menschutkin-Type Reaction of Phenethyl Arenesulfonates with Pyridine
Soo-Dong YohJong-Hwan ParkKyung-A LeeIn-Sook Han
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1987 Volume 60 Issue 3 Pages 1149-1152


Kinetic investigation of β-phenylethyl arenesulfonates with pyridine in acetonitrile revealed that the rates of these reactions which were lower than those of the reaction of benzyl benzenesulfonate with pyridine in acetone were increased with raising temperatures and pressures. The activation volumes were comparable to those of benzyl system, but activation entropies were negatively larger than those of benzyl system. From these phenomena it can be deduced that phenethyl system has more SN2 character in the transition state, comparing with the reaction of benzyl system. With raising pressures the Hammett reaction parameters (ρ) were decreased, indicating that the reaction is probably closer to tight SN2 character at higher pressures.

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