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Towards quantifying the role of hydrogen bonding within amphiphile self-association and resultant aggregate formation

White, L. J., Wells, N. J., Blackholly, L. R., Shepherd, H. J., Wilson, B., Bustone, G. P., Runacres, T. J., Hiscock, J.R. (2017) Towards quantifying the role of hydrogen bonding within amphiphile self-association and resultant aggregate formation. Chemical Science, 8 . pp. 7620-7630. ISSN 2041-6520. E-ISSN 2041-6539. (doi:10.1039/C7SC03888G)

Abstract

Herein, we present a series of five tetrabutylammonium (TBA) sulfonate–urea amphiphilic salts. In solution these amphiphilic salts have been shown to form a variety of self-associated species. The proportion and type of which are both solvent and concentration dependent. In DMSO-d6 a variety of NMR experiments provide evidence towards the formation of mainly dimeric over larger aggregate species. Increasing the percentage of water was shown to increase the concentration of the larger aggregates over dimers in solution. A correlation was established between critical micelle concentration (CMC) values obtained in a 1?:?19 EtOH?:?H2O mixture, dimeric self-association constants obtained in a DMSO-d6 – 0.5% H2O and the results of simple semi-empirical PM6 computational modelling methods. This approach begins to quantify the role of hydrogen bonding in amphiphile self-association and the effects it imparts on surfactant properties. This consequently provides preliminary evidence that these properties maybe predicted by simple low level computational modelling techniques.

Item Type: Article
DOI/Identification number: 10.1039/C7SC03888G
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Jennifer Hiscock
Date Deposited: 11 Oct 2017 15:46 UTC
Last Modified: 23 Jan 2020 04:13 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/63960 (The current URI for this page, for reference purposes)
Hiscock, J.R.: https://orcid.org/0000-0002-1406-8802
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