Interactions Of Chiral Molecules With An (r)‐n‐(3,5‐dinitrobenzoyl) Phenylglycine HPLC Stationary Phase

Abstract

Forty different chiral molecules were studied by liquid chromatography with a Pirkle‐type, (R)‐N‐(3,5‐dinitrobenzoyl) phenylglycine (DNBPG), chiral stationary phase column. The dramatic effect of a small molecular change on chiral recognition was demonstrated using DL‐amino acid derivatives. The inductive effect on chiral recognition was also studied using trifluoro‐, trichloro‐, dichloro‐, monochloroacetyl, and acetyl derivatives of four different chiral amines. The study of the enantiomer separation of 11 different crown ethers of 2,2′‐binaphthyldiyl showed that the rigidity of the chiral center can be an additional parameter in chiral recognition for the DNBPG phase but not for a β‐cyclodextrin bonded chiral phase. It is apparent from this study that steric effects, inductive effects, and molecular rigidity play important roles in chiral recognition with DNBPG chiral stationary phases. Copyright © 1990 Wiley‐Liss, Inc.

Department(s)

Chemistry

Keywords and Phrases

chiral recognition mechanism; chiral stationary phases; column liquid chromatography; derivatization effects

International Standard Serial Number (ISSN)

1520-636X; 0899-0042

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 Wiley, All rights reserved.

Publication Date

01 Jan 1990

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