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1Department of Chemistry, Faculty of Science, Universiti Malaya, 50603 Kuala Lumpur, Malaysia.
The Journal of Organic Chemistry
|May 18, 2000
Summary
Cetyltrimethylammonium bromide (CTABr) micelles nonlinearly decrease reaction rates between amines and phenyl salicylate (PS(-)). This behavior is explained by a pseudophase micellar model, providing insights into micellar binding constants.
Area of Science:
- Physical Chemistry
- Chemical Kinetics
- Supramolecular Chemistry
Background:
- Surfactant micelles influence chemical reaction rates.
- Understanding these effects is crucial for reaction mechanism elucidation.
Purpose of the Study:
- To investigate the impact of cetyltrimethylammonium bromide (CTABr) micelles on the kinetics of nucleophilic reactions.
- To quantify the binding of ionized phenyl salicylate (PS(-)) to CTABr micelles.
Main Methods:
- Studied second-order rate constants (k(n)(obs)) for reactions between amines (piperidine, n-butylamine) and PS(-).
- Analyzed data using a pseudophase micellar model at constant temperature (35°C) and varying CTABr concentrations.
- Investigated the effect of sodium bromide (NaBr) concentration on micellar binding constants.
Main Results:
- Observed a nonlinear decrease in k(n)(obs) with increasing CTABr concentration ([D(n)]).
- The pseudophase model successfully described the kinetic data, yielding micellar binding constants (K(S)) for PS(-).
- Found that NaBr concentration affects K(S) according to an empirical relationship.
Conclusions:
- CTABr micelles significantly alter the reaction kinetics of amines with PS(-).
- The pseudophase model provides a valid framework for understanding these micellar effects.
- The study quantifies the interaction between PS(-) and CTABr micelles, influenced by ionic strength.