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The Hammett Equation and Micellar Effects on S N 2 Reactions of Methyl Benzenesulfonates ?ms The Role of Micellar Polarity
Author(s) -
Brinchi Lucia,
Di Profio Pietro,
Germani Raimondo,
Savelli Gianfranco,
Spreti Nicoletta,
Bunton Clifford A.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200012)2000:23<3849::aid-ejoc3849>3.0.co;2-p
Subject(s) - chemistry , substituent , sn2 reaction , micelle , pulmonary surfactant , cationic polymerization , hammett equation , micellar solutions , polar , medicinal chemistry , organic chemistry , aqueous solution , kinetics , reaction rate constant , biochemistry , physics , astronomy , quantum mechanics
Substituent effects on the reaction of H 2 O, OH − , and Br − with p ‐substituted methyl benzenesulfonates in cationic micelles of cetyl trialkylammonium ion surfactants ( n ‐C 16 H 33 NR 3 X, X = OH, Br, R = Me, Et, n Pr, n Bu) and in water were analyzed by using the Hammett equation. Values of ρ in the various media confirm that micellar interfacial regions are less polar than water and polarities decrease with increasing bulk of the surfactant head‐group.