Investigation on the chiral discrimination mechanism using an axially asymmetric binaphthalene-based stationary phase for high-performance liquid chromatography

Shuichi Oi, Hiroyuki Ono, Hideyuki Tanaka, Yutaka Matsuzaka, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The chiral discrimination mechanism of 3,5-dinitrophenyl-derivatized enantiomeric alcohols, amines and carboxylic acids using a chiral stationary phase (CSP) prepared by bonding (aS)-1,1′-binaphthyl-2,2′-dicarboxylic acid to 3-aminopropylsilanized silica gel was investigated. Studies of the elution behaviour of a series of structurally related analytes on the CSP and 1H NMR measurements of a solubilized model compound of the CSP and analytes indicated that a π-donor-acceptor interaction between one of the naphthalene planes of the CSP and the 3,5-dinitrophenyl ring of the analyte cooperates with the dipole stacking interaction between two sets of amide linkages of the CSP and the analytes to determine the stability of the diastereomeric adsorbates.

Original languageEnglish
Pages (from-to)75-86
Number of pages12
JournalJournal of Chromatography A
Volume659
Issue number1
DOIs
Publication statusPublished - 1994 Jan 21

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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