Issue 3, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

A comparative study of the determination of the stability constants of inclusion complexes of p-sulfonatocalix[4]arene with amino acids by RP-HPLC and 1H NMR

Olga I. Kalchenko,a   Florent Perret,bc   Nicole Morel-Desrosiersc  and  Anthony W. Coleman*b  

* Corresponding authors

a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya, 5, 02094, Kiev, Ukraine

b IBCP, CNRS UMR 5086, 7, Passage du Vercors, Lyon Cedex 07, France
E-mail: aw.coleman@ibcp.fr

c Laboratoire de Thermodynamique des Solutions et des Polymères, UMR CNRS 6003, Université Blaise Pascal (Clermont-Ferrand II), 24 avenue des Landais, Aubière cedex, France

Abstract

Reversed-phase high-performance liquid chromatography (Separon SGX C 18, UV detection at 254 nm and acetonitrile–water–trifluoroacetic acid (70 ∶ 30 ∶ 0.5, v/v), and methanol–water–trifluoroacetic acid (3 ∶ 97 ∶ 0.5, v/v) as mobile phases) was applied to the study of the host–guest complexation of p-sulfonatocalix[4]arene (SC[4]A) with amino acids as guests in the mobile phase. It was established that the formation of the inclusion complexes results in changes in the retention times of the amino acids. Stability constants of the complexes were determined. The variations in stability constants may be explained in terms of the various interactions (ion-pairing, hydrophobic, aromatic–aromatic and electrostatic interactions) that may occur between a given amino acid and SC[4]A. For the amino acids aspartic acid and proline the association constants were also derived from 1H NMR experiments.

Graphical abstract: A comparative study of the determination of the stability constants of inclusion complexes of p-sulfonatocalix[4]arene with amino acids by RP-HPLC and 1H NMR

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Article information

DOI
https://doi.org/10.1039/B005497F
Article type
Paper
Submitted
10 Jul 2000
Accepted
19 Dec 2000
First published
07 Feb 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 258-263

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A comparative study of the determination of the stability constants of inclusion complexes of p-sulfonatocalix[4]arene with amino acids by RP-HPLC and 1H NMR

O. I. Kalchenko, F. Perret, N. Morel-Desrosiers and A. W. Coleman, J. Chem. Soc., Perkin Trans. 2, 2001, 258 DOI: 10.1039/B005497F

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