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

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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.

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

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Publication details

The article was received on 05 Sep 2017, accepted on 21 Sep 2017 and first published on 26 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC03888G
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Towards quantifying the role of hydrogen bonding within amphiphile self-association and resultant aggregate formation

    L. J. White, N. J. Wells, L. R. Blackholly, H. J. Shepherd, B. Wilson, G. P. Bustone, T. J. Runacres and J. R. Hiscock, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03888G

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