Effects from hydrogen bonding and rigidity on selectivity in tartaric acid-based chiral selectors for enantioselective liquid chromatography

Tartaric acid‐based selectors 1 ((R,R)‐O,O′‐Bis(dimethylbenzoyl)‐N,N′‐diallyl‐N,N′‐dimethyl tartaramide) and 2 ((R,R)‐N‐allyl‐O,O′‐bis(dimethylbenzoyl) tartarimide) were synthesized, immobilized on silica, and evaluated as chiral stationary phases in enantioselective chromatography. Comparison with...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) Vol. 15; no. 9; pp. 787 - 793
Main Authors: Oxelbark, Joakim, Sellén, Inga-Britt
Format: Journal Article
Language:English
Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 2003
Subjects:
CD spectroscopy
chiral chromatography
tartar amide
tartar imide
ISSN:0899-0042, 1520-636X
Online Access:Get full text
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Summary:Tartaric acid‐based selectors 1 ((R,R)‐O,O′‐Bis(dimethylbenzoyl)‐N,N′‐diallyl‐N,N′‐dimethyl tartaramide) and 2 ((R,R)‐N‐allyl‐O,O′‐bis(dimethylbenzoyl) tartarimide) were synthesized, immobilized on silica, and evaluated as chiral stationary phases in enantioselective chromatography. Comparison with the commercially available column Kromasil‐CHI‐1, based on selector 3 ((R,R)‐O,O′‐Bis(dimethylbenzoyl)‐N,N′‐diallyl tartaramide) resulted in the conclusion that amide NH functions are essential to chiral recognition on this sorbent. Furthermore, NH functions contribute significantly to retention of analytes except for alcohols. It was also found that flexibility of the benzoyl moieties is essential to selectivity. Chirality 15:787–793, 2003. © 2003 Wiley‐Liss, Inc.
Bibliography:istex:17ABB7DD0C0F209016B5D25F07D80ECF9D89A002
AstraZeneca R&D Mölndal, EKA Chemicals AB, SSF/Selchem
ark:/67375/WNG-JCS1M92C-H
ArticleID:CHIR10299
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.10299