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Issue 7, 2013
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Competition between surfactant micellization and complexation by cyclodextrin

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Abstract

Supramolecular property systems composed of alkyltrimethylammonium surfactants and β-cyclodextrin were studied by means of a chemical probe. Solvolysis of 4-methoxybenzenesulfonyl chloride (MBSC) was used in the mixed systems with the aim of being able to determine the concentration of uncomplexed cyclodextrin in equilibrium with the micellar system. The surfactants used enabled us to vary the length of the hydrocarbon chain between 6 and 18 carbon atoms. In all cases the existence of a significant concentration of uncomplexed CD was observable in equilibrium with the micellar system. The percentage of uncomplexed cyclodextrin increases both on increasing and decreasing the surfactant alkyl chain length, being minimal for alkyl chains between 10–12 carbon atoms. This behavior is a consequence of two simultaneous processes: complexation of surfactant monomers by the cyclodextrin and surfactant self-assembly to form micellar aggregates. By using Gibbs free energies for micellization and surfactant complexation by β-CD, we can quantitatively explain the observed behavior.

Graphical abstract: Competition between surfactant micellization and complexation by cyclodextrin

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Publication details

The article was received on 10 Jul 2012, accepted on 06 Nov 2012 and first published on 06 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26318A
Citation: Org. Biomol. Chem., 2013,11, 1093-1102
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    Competition between surfactant micellization and complexation by cyclodextrin

    M. Cepeda, R. Daviña, L. García-Río, M. Parajó, P. Rodríguez-Dafonte and M. Pessêgo, Org. Biomol. Chem., 2013, 11, 1093
    DOI: 10.1039/C2OB26318A

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