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Effects of anionic micelles on intramolecular general base‐catalysed aminolysis of ionized phenyl salicylate (PS −3 )
Author(s) -
Khan M. Niyaz
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199901)12:1<1::aid-poc82>3.0.co;2-d
Subject(s) - chemistry , aminolysis , piperidine , pyrrolidine , reaction rate constant , micelle , medicinal chemistry , amine gas treating , sodium salicylate , nucleophile , intramolecular force , binding constant , butylamine , organic chemistry , kinetics , catalysis , aqueous solution , binding site , physics , quantum mechanics , biochemistry
The effects of micelles of sodium dodecyl sulphate (SDS) on the rates of reactions of ionized phenyl salicylate (PS − ) with n ‐butylamine, piperidine and pyrrolidine were studied at 35 °C. Pseudo‐first‐order rate constants ( k obs ) show a linear increase with increase in the total concentration of amine ([Am] T ) at a constant [SDS]. An increase in the total concentration of SDS from 0.0 to 0.2 mol dm −3 results in a decrease in the observed nucleophilic second‐order rate constants by the factors of ca 2.6, 5.2 and 3.9 for the reactions of PS − with n ‐butylamine, piperidine and pyrrolidine, respectively. The rate constants, k obs , show a non‐linear increase with increase in [NaOH] from 0.0 to 0.04 mol dm −3 at a constant [SDS] and [Am] T . The observed results of aminolysis of PS − in the presence of SDS micelles are rationalized in the light of the pseudophase model of micelles. Copyright © 1999 John Wiley & Sons, Ltd.