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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 5
May 20, 1987 

Solvolysis of 2-Phenylethyl Benzenesulfonates in Methanol-Water Mixtures
Goang Lae Han, Jin Ha Park, Ikchoon Lee*
Solvolyses of 2-phenylethyl benzenesulfonates have been studied in methanol-water mixtures. Cross interaction constants, ρYZ, between substituents Y in the substrate and Z in the leaving group indicated somewhat closer distance between the two substituents than expected for the reaction system, which supported the involvment of phenyl group assisted pathway in the solvolysis. A smaller magnitude of ρYZ for MeOH was interpreted as the enhencement of solvent assisted pathway since MeOH is more nucleophilic than H2O. Other selectivity parameters, Winstein coefficient m, Hammett's ρ+Y and ρZ, as well as activation parameters supported the participation of aryl assisted and aryl unassisted pathways in the SN2 process of the solvolysis reaction.
393 - 398
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