Separation of 2-naphthol atropisomers on cyclofructan-based chiral stationary phases

Lillian A. Frink, Alain Berthod, Qing Long Xu, Hongyin Gao, Laszló Kurti, Daniel W. Armstrong

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A set of fifteen 2-naphthol-derived atropisomers were evaluated on three different cyclofructan-based chiral stationary phases (CSP). The cyclofructan CSPs were a dimethylphenyl-derivatized cyclofructan 7 (CF7-DMP), a isopropyl (CF6-P) and a R-naphthylethyl cyclofructan 6 (CF6-RN) derivative, all bonded to 5-µm spherical fully porous silica particles packed into three 25 cm × 4.6 mm columns (commercially available as Larihc columns). The 15 atropisomers were analyzed in the normal-phase mode with heptane/alcohol mobile phases. The CF7-DMP column was the most effective partially or fully separating 14 of the 15 compounds (93%). All 15 compounds could be separated by at least one cyclofructan column. Five compounds could be partially or fully separated by all three CSPs. The effect of ethanol, 2-propanol and butanol as 5 and 10% v/v polar modifiers in heptane was studied. A prototype 15 cm × 4.6 mm column packed with superficially porous 2.7 µm CF6-P bonded particles was tested with the same set of compounds and a standard HPLC system. The increased efficiency and solvent saving were significant.

Original languageEnglish (US)
Pages (from-to)710-717
Number of pages8
JournalJournal of Liquid Chromatography and Related Technologies
Volume39
Issue number15
DOIs
StatePublished - Sep 13 2016

Keywords

  • 2-naphthol phenyl derivatives
  • Atropisomer separation
  • cyclofructan selectors
  • superficially porous particles

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Pharmaceutical Science
  • Clinical Biochemistry

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