Complexation of amino acids derivatives in water by calix[4]arene phosphonic acids |
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Authors: | Joanna Dziemidowicz Dariusz Witt Janusz Rachoń |
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Institution: | 1. Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952, Gdansk, Poland
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Abstract: | Series of the calix4]arene phosphonic acids with various substituents at the lower rim was synthesized. Complexing properties of these receptors towards methyl esters of six amino acids strongly depended on the calix4]arene conformation flexibility. The complex formation processes were monitored using 1H NMR spectroscopy (deuterated phosphate buffer at pD 7.3, 22 °C) and association constant values were evaluated. Inherently mobile calix4]arene molecule 3 occurred in cone conformation in aqueous solution turned out to be more effective in complexation of the basic amino acids methyl esters compared to the rigid 2 and flexible 4. Mixed 1:2 and 2:1 (host–guest) complexes were observed for compound 1 with all amino acids methyl esters. |
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