Axially dissymmetric bianthracene-based chiral stationary phase for the high-performance liquid chromatographic separation of enantiomers

Shuichi Oi, Hiroyuki Ono, Hideyuki Tanaka, Masayuki Shijo, Sotaro Miyano

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Enantiomerically pure (aR)-1,1′-bianthracene-2,2′-dicarboxylic acid is prepared and bonded to a 3-aminopropylsilanized silica via an amide linkage to afford a novel chiral stationary phase (CSP 2) for high-performance liquid chromatographic separation of enantiomers. The performance of CSP 2 is compared with that of the previously prepared binaphthalene-based CSP (CSP 1), which was obtained by bonding axially dissymmetric (aS)-1,1′-binaphthalene-2,2′-dicarboxylic acid to the silica. As is expected from the chiral discrimination mechanism proposed for CSP 1, in which simultaneous π-donor-acceptor interaction and dipole-stacking interaction between the CSP and the analytes play a critical role for the separation of enantiomers, CSP 2 shows a greatly improved performance as compared with CSP 1 in the separation of a wide range of enantiomeric amino acids, amines, alcohols and carboxylic acids as the 3,5-dinitrophenyl derivatives.

Original languageEnglish
Pages (from-to)35-46
Number of pages12
JournalJournal of Chromatography A
Volume679
Issue number1
DOIs
Publication statusPublished - 1994 Sep 9

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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