Chiral stationary phases consisting of axially dissymmetric 2′-substituted-1,1′-binaphthyl-2-carboxylic acids bonded to silica gel for high-performance liquid chromatographic separation of enantiomers

Shuichi Oi, Masayuki Shijo, Hideyuki Tanaka, Sotaro Miyano, Junzo Yamashita

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

Seven chiral stationary phases (CSPS) were prepared by bonding axially dissymmetric 2′-substituted-1,1′- binaphthyl-2-carboxylic acids to aminoalkylsilanized silica gels through an amide linkage, and the effect of the 2′-substituents (CN, COOH, CONH2, CONHEt, CONEt2 and OCH3) was investigated for the high-performance liquid chromatographic (HPLC) separation of enantiomers. Among these CSPS, that which had a 2′-carboxyl substituent showed the best performance and efficiently discriminated several enantiomeric amino acids, amines and alcohols as their 3,5-dinitrophenyl derivatives, and biaryls bearing 2,2′-polar substituents, by normal-phase HPLC. Stereoselective π-donor-acceptor interaction and dipole stacking interaction between the CSPs and the analytes seem to play a critical role in the enantioseparation.

Original languageEnglish
Pages (from-to)17-28
Number of pages12
JournalJournal of Chromatography A
Volume645
Issue number1
DOIs
Publication statusPublished - 1993 Aug 13

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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