High-performance liquid chromatographic enantioseparation of 1-(phenylethylamino)- or 1-(naphthylethylamino)methyl-2-naphthol analogs and a temperature-induced inversion of the elution sequence on polysaccharide-based chiral stationary phases

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Abstract

The stereoisomers of five 1-(phenylethylamino)methyl-2-naphthol analogs or 1-(naphthylethylamino)methyl-2-naphthol analogs containing two chiral centers were directly separated on chiral stationary phases containing the chiral selectors cellulose tris-(3,5-dimethylphenyl) carbamate (Lux Cellulose-1), cellulose tris-(3-chloro-4-methylphenyl) carbamate (Lux Cellulose-2) and amylose tris-(5-chloro-2-methylphenyl) carbamate (Lux Amylose-2). Experiments were performed in normal-phase mode in a wide temperature range -5 to 70°C. Thermodynamic parameters and Tiso values were calculated from plots of lnk or lnα vs. 1/T. -Δ(ΔH°) ranged from 1.0 to 4.7kJmol-1, -Δ(ΔS°) from 1.6 to 11.0Jmol-1K-1 and -Δ(ΔG°) from 0.1 to 1.5kJmol-1. The sequence of elution of the stereoisomers was determined in all cases and in one case a temperature-induced inversion of the elution sequence was observed.

Original languageEnglish
Pages (from-to)4869-4876
Number of pages8
JournalJournal of Chromatography A
Volume1218
Issue number30
DOIs
Publication statusPublished - Jul 29 2011

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Keywords

  • 1-(Naphthylethylamino)methyl-2-naphthol analogs
  • 1-(Phenylethylamino)methyl-2-naphthol analogs
  • Column liquid chromatography
  • Enantiomer separation
  • Lux Amylose-2 column
  • Lux Cellulose-1 column
  • Lux Cellulose-2 column

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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