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Combined Theoretical and Experimental Study of the Complexation of a Hexaarylbenzene-Based Receptor with the Potassium Cation

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Abstract

In this study, non-covalent binding interactions of the hexaarylbenzene-based receptor (R) with the potassium cation have been investigated. Employing quantum mechanical density functional theory calculations, the most probable structure of the KR + complex species was predicted. In this complex, the K+ cation synergistically interacts with the polar ethereal oxygen fence and with the central hydrophobic benzene bottom via cation–π interaction. The strength of the KR + complex was evaluated experimentally by affinity capillary electrophoresis. From the dependence of the effective electrophoretic mobility of the receptor R on the concentration of the potassium ion in the background electrolyte, the thermodynamic binding (stability, association) constant (K KR) of the KR + complex in methanol was evaluated as log10 K KR = 3.20 ± 0.22.

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Acknowledgments

This work was supported by the Czech Science Foundation, Grants Nos. 203/08/1428, 203/09/0675 and P205/10/2280; by the Research Project No. AV0Z40550506 of the Academy of Sciences of the Czech Republic, by the Ministry of Education, Youth and Sports of the Czech Republic, Project No. MSM6383917201 and by the Grant Agency of Faculty of Enviromental Sciences, Czech University of Life Sciences, Prague, Project No.: 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society”. R.R. thanks the National Science Foundation for the financial support.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10, Prague 6, Czech Republic

    Sille Ehala & Václav Kašička

  2. Institute of Macromolecular Chemistry, v.v.i., Academy of Sciences of the Czech Republic, Heyrovského nám. 2, 162 06, Prague 6, Czech Republic

    Petr Toman

  3. Faculty of Enviromental Sciences, Czech University of Life Sciences Prague, Kamýcká 129, 165 21, Prague 6, Czech Republic

    Emanuel Makrlík

  4. Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, Wisconsin, 53201-1881, USA

    Rajendra Rathore

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  1. Sille Ehala
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Correspondence to Václav Kašička.

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Ehala, S., Toman, P., Makrlík, E. et al. Combined Theoretical and Experimental Study of the Complexation of a Hexaarylbenzene-Based Receptor with the Potassium Cation. J Solution Chem 41, 1812–1824 (2012). https://doi.org/10.1007/s10953-012-9896-2

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