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Complexation of calix[4]arenehydroxymethylphosphonic acids with amino acids. Binding constants determination of the complexes by HPLC method

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Abstract

Host–Guest complexation process of calixarenehydroxymethylphosphonic acids with 10 amino acids in solution H2O/MeCN (99:1) had been studied. Binding constants of the inclusion complexes from the dependence between capacity factors of the Guest and the calixarene-Host concentration in the mobile phase had been calculated. It was shown the binding constants depend on the nature of the amino acid residue, conformation of the calixarene skeleton, quantity of phosphoryl groups at the upper rim. In accordance with molecular calculation the complexation is determined by the electrostatic interactions between the positively charged nitrogen atom of amino acid and the negatively charged oxygen atom of phosphonic group of calixarene molecule, hydrogen bonds, π–π, CH–π and solvatophobic, interactions.

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Acknowledgments

The work is partially supported by the State Fund for Fundamental Researches of Ukraine (grant F 40/78-2011). The authors are grateful to Dr. O.M. Chernega for fruitful discussion.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska str. 5, Kiev, 02660, Ukraine

    Olga Kalchenko, Sergiy Cherenok, Olexander Yushchenko & Vitaly Kalchenko

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  1. Olga Kalchenko
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  2. Sergiy Cherenok
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  3. Olexander Yushchenko
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  4. Vitaly Kalchenko
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Correspondence to Olga Kalchenko.

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Kalchenko, O., Cherenok, S., Yushchenko, O. et al. Complexation of calix[4]arenehydroxymethylphosphonic acids with amino acids. Binding constants determination of the complexes by HPLC method. J Incl Phenom Macrocycl Chem 76, 29–36 (2013). https://doi.org/10.1007/s10847-012-0169-x

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