Adsorption of the enantiomers of 3-chloro-1-phenyl-propanol on silica-bonded chiral quinidine carbamate

Leonid Asnin, Krzysztof Kaczmarski, Attila Felinger, Fabrice Gritti, Georges Guiochon

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19 Citations (Scopus)

Abstract

The interactions of 3-chloro-1-phenyl-propanol with a quinidine carbamate-bonded chiral stationary phase under NPLC conditions were studied by measuring the adsorption isotherm data of its enantiomers by frontal analysis, modeling these data with a suitable isotherm model, and comparing the experimental overloaded elution band profiles with those calculated with this isotherm and the equilibrium dispersive model of liquid chromatography. The affinity energy distribution was calculated from the adsorption isotherm data. The results show that the surface of the adsorbent is heterogeneous and exhibits a bimodal adsorption energy distribution. This fact is interpreted in terms of the presence of two different types of adsorption sites on the stationary phase, nonselective and enantioselective sites. Albeit the bi-Langmuir isotherm model successfully accounts for the single-component data corresponding to both enantiomers, the competitive bi-Langmuir isotherm model does not allow an accurate prediction of the overloaded band profiles of the racemic mixture. Thermodynamic data are drawn for explanation. Some aspects of the retention mechanism are discussed in the light of the data obtained.

Original languageEnglish
Pages (from-to)158-170
Number of pages13
JournalJournal of Chromatography A
Volume1101
Issue number1-2
DOIs
Publication statusPublished - Jan 6 2006

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Keywords

  • 3-Chloro-1-phenyl-propanol
  • Adsorption isotherm
  • Chiral stationary phase
  • Competitive adsorption
  • Enantiomeric separation
  • Quinidine carbamate

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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