The study of the Complexation of Calix[4]arene and Calix[4]resorcinarene with resin acids by the RP HPLC method. binding constants determination

O. I. Kalchenko, S. O. Cherenok, A. V. Solovyov, V. V. Gorbatchuk, S. Yu. Suikov, V. I. Kalchenko

Abstract


The Host-Guest complexation of octakis-(diphenoxyphosphoryloxy)tetramethylcalix[4]resorcinarene (CR) and 5,17-bis-(N-tolyliminomethyl)-25,27-dipropoxycalix[4]arene (CA) with 6 diterpenoid (resin) acids has been studied by the reversed phase high-performance liquid chromatography (RP HPLC). The chromatographic characteristics (retention time tR and retention factor k’) of resin acids have been determined. The lipophilicity values log P of the acids, binding constants KA (395-682 M-1 for CR and 844-1268 M-1 for CA), as well as Gibbs free energies ∆G (-14.79 – -16.14 kJ/mol for CR and -16.70 – -17.67 kJ/mol for CA) of the complexes with resin acids have been calculated. Molecular modelling of CA complexes has revealed the presence of hydrogen bonds between carboxylic groups of acids and nitrogen atoms of imino groups at the upper rim or oxygen atoms of the hydroxyl groups at the lower rim of the CA macrocycle. Molecular modelling of CR complexes has shown the presence of hydrogen bonds between carboxylic groups of acids and oxygen atoms of diphenoxyphosphoryloxy groups at the upper rim of the CR macrocycle. The effect of log P values on KA values of the CR/CA complexes has been assessed. The linear dependence of the binding constants on the acid lipophilicity indicates a significant role of solvophobic interactions on the complexation. The relationship between supramolecular (KA) and physicochemical (log P, pKa) characteristics of acids has been determined.

Keywords


calix[4]arenes; resin acids; reversed-phase high performance liquid chromatography; inclusion complexes; binding constants; molecular modelling

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References


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DOI: https://doi.org/10.24959/ophcj.16.884

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)