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Calix[4]arene-bis(t-octylbenzo-18-crown-6) as an extraordinarily effective macrocyclic receptor for the univalent thallium cation

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Abstract

From extraction experiments and \( \gamma \)-activity measurements, the exchange extraction constant corresponding to the equilibrium Tl+ (aq) + 1·Cs+ (org) ⇔ 1·Tl+ (org) + Cs+ (aq) taking place in the two-phase water–phenyltrifluoromethyl sulfone (abbrev. FS 13) system (1 = calix[4]arene-bis(t-octylbenzo-18-crown-6); aq = aqueous phase, org = FS 13 phase) was evaluated as log K ex (Tl+, 1·Cs+) = 1.7 ± 0.1. Further, the extraordinarily high stability constant of the 1·Tl+ complex in FS 13 saturated with water was calculated for a temperature of 25 °C: log β org(1·Tl+) = 13.1 ± 0.2. Finally, by using quantum mechanical DFT calculations, the most probable structure of the cationic complex species 1·Tl+ was derived. In the resulting 1·Tl+ complex, the “central” cation Tl+ is bound by eight bond interactions to six oxygen atoms from the respective 18-crown-6 moiety and to two carbons of the corresponding two benzene rings of the parent receptor 1 via cation–π interaction.

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Acknowledgments

This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No.: 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society,” by the Czech Ministry of Education, Youth, and Sports (Project MSM 6046137307), and by the Czech Science Foundation (Project P 205/10/2280). Finally, the participation of B.A.M. was sponsored by the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, U. S. Department of Energy.

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Authors and Affiliations

  1. Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21, Prague 6, Czech Republic

    E. Makrlík

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

    P. Toman

  3. Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic

    P. Vaňura

  4. Chemical Sciences Division, Oak Ridge National Laboratory, P.O. Box 2008, Oak Ridge, TN, 37831-6119, USA

    B. A. Moyer

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  1. E. Makrlík
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  2. P. Toman
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Correspondence to E. Makrlík.

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Makrlík, E., Toman, P., Vaňura, P. et al. Calix[4]arene-bis(t-octylbenzo-18-crown-6) as an extraordinarily effective macrocyclic receptor for the univalent thallium cation. Struct Chem 25, 847–852 (2014). https://doi.org/10.1007/s11224-013-0349-3

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