Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2-naphthol and 2-(α-aminobenzyl)-1-naphthol analogs

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Abstract

The enantiomers of 1-(α-aminobenzyl)-2-naphthol and 2-(α-aminobenzyl)-1-naphthol analogs were separated isothermally on a celllulose-tris-3,5-dimethylphenyl carbamate-based chiral stationary phase (Chiralcel OD-H), at 10°C increments in the range of 5-35°C, using n-hexane/2-propanol/diethylamine as mobile phase. The mobile phase composition and temperature were varied to achieve baseline resolutions in a single chromatographic run. The dependence of the natural logarithms of selectivity factors, In α, on the inverse of temperature, 1/T, was used to determine the thermodynamic data of the enantiomers. The thermodynamic data revealed that all the compounds in this study separate via the same enthalpy-driven chiral recognition mechanism.

Original languageEnglish
Pages (from-to)2505-2510
Number of pages6
JournalJournal of separation science
Volume28
Issue number18
DOIs
Publication statusPublished - Dec 1 2005

Keywords

  • 1-(α-Aminobenzyl)-2-naphthol analogs
  • 2-(α-Aminobenzyl)-1-naphthol analogs
  • Enantiomer separation
  • HPLC
  • Temperature effect

ASJC Scopus subject areas

  • Analytical Chemistry
  • Filtration and Separation

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