Enantioseparation of Amino Acids and Amino Alcohols on a Chiral Stationary Phase Derived from L‐Alanyl‐ and Piperidinyl‐Disubstituted Cyanuric Chloride

Abstract

AbstractA silica‐base chiral stationary phase (CSP) derived from L‐alanyl‐ and piperidinyl‐disubstituted cyanuric chloride was prepared for the enantioseparation of methyl esters of N‐(3,5‐dinitrobenzoyl)amino acids and amino alcohols. This CSP provides good chiral recognition and effective separation of enantiomers of both methyl esters of N‐(3,5‐dinitrobenzoyl)amino acids, except for proline, and N‐(3,5‐dinitrobenzoyl)amino alcohols by high‐performance liquid chromatography. The enantioselectivity depends mainly on three preferential interactions which include a π‐π interaction and two hydrogen‐bonding interactions. However, steric interaction between substituents attached to the chiral center of chiral selectands and the chiral selector also plays a significant role in chiral recognition. Comparison of chromatographic results of the CSP prepared in this study with those of the CSP containing pyrrolidinyl group attached to the s‐triazine moiety, reported previously (J. Chromatogr. A, 722 (1996) 189), reveals that influences of steric interaction and the basic nature of piperidinyl substituent attached to the s‐triazine ring of the chiral selector on chiral discrimination may not be neglected.