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18-crown-6-aminophenol isomer complexes studied by RPLC

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  • Column Liquid Chromatography
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Summary

The reserved-phase liquid chromatography retention of aminophenol isomer was investigated over a concentration range of 18-crown-6 (c: 0–0.15 M) using a C18 as the stationary phase and a phosphate buffer pH 2 as the mobile phase. A theoretical treatment was developed to investigate the effect of the polyether on the equilibrium between the solutes with the C18 phase and the aqueous medium respectively. This was found to be adequate to accurately describe the isomer retention behavior when c varied. It was expected that the addition of 18-crown-6 was responsible for an increase in the solute affinity for the C18 stationary phase due to complex formation and blockage of the polar amino group of the solute. The thermodynamic parameter variations were calculated using van’t Hoff plots. The enthalphy-entropy compensation was analyzed in relation to this retention model to confirm the influence of the modifier on the solute affinity towards the C18 phase. From the experimental data, the complexation and transfer constants for the different species were determined for the three isomers. This indicated that the hydroxyl group of the solute governed both the complexation and retention processes via hydrogen bonding and steric effects.

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Authors and Affiliations

  1. Laboratoire de Chimie Analytique, Faculté de Parmacie, Domaine de la Merci, 38700, La Tronche, France

    E. Peyrin, A. Villet, C. Grosset & J. Alary

  2. Laboratoire de Chimie Analytique, Faculté de Médecine et Pharmacie, Place Saint-Jacques, 25030, Besançon cedex, France

    Y. C. Guillaume

Authors
  1. E. Peyrin
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  2. Y. C. Guillaume
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  3. A. Villet
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  4. A. Ravel
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  5. C. Grosset
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  6. J. Alary
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Peyrin, E., Guillaume, Y.C., Villet, A. et al. 18-crown-6-aminophenol isomer complexes studied by RPLC. Chromatographia 52, 584–588 (2000). https://doi.org/10.1007/BF02789755

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  • DOI: https://doi.org/10.1007/BF02789755

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