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

J Sep Sci. 2005 Dec;28(18):2505-10. doi: 10.1002/jssc.200500138.

Abstract

The enantiomers of 1-(alpha-aminobenzyl)-2-naphthol and 2-(alpha-aminobenzyl)-1-naphthol analogs were separated isothermally on a cellulose-tris-3,5-dimethylphenyl carbamate-based chiral stationary phase (Chiralcel OD-H), at 10 degrees C increments in the range of 5-35 degrees 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 alpha, 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry / methods
  • Chromatography, High Pressure Liquid / methods*
  • Hot Temperature
  • Models, Chemical
  • Naphthols / analysis*
  • Naphthols / isolation & purification*
  • Stereoisomerism
  • Temperature
  • Thermodynamics

Substances

  • Naphthols
  • 1-amino-2-naphthol