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Kinetics of the nucleophilic substitution of benzyl‐tributylammonium bromide with allyl, butyl, and benzyl chlorides and with benzyl acetate and benzyl ether
Author(s) -
Wang TenTsai,
Chang ChyiHuang,
Huang TingChia
Publication year - 1996
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/(sici)1097-4601(1996)28:8<615::aid-kin7>3.0.co;2-y
Subject(s) - chemistry , benzyl bromide , medicinal chemistry , toluene , reactivity (psychology) , allyl bromide , nucleophilic substitution , bromide , ether , reaction rate constant , benzyl chloride , nucleophile , solvent , kinetics , catalysis , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
In this study, we investigated the kinetics of the nucleophilic substitutions, RX + (BzBu 3 NBr) ← → RBr + (BzBu 3 NX), where R = allyl, Bu and Bz, when X = Cl; and X = AcO and BzO when R = Bz. The forward and backward rate constants in addition to the activation energies for R = allyl and Bu were also determined. However, only the rate constants at 35°C were determined for the benzyl compounds with toluene as the solvent to reduce the reaction rate. Moreover, the effects of the structures of the groups R and the leaving groups X on the reactivity were compared. Results in this study can provide valuable information for future studies involving the phase transfer catalyzed displacements. © 1996 John Wiley & Sons, Inc.