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Separations of chiral aryl alcohol derivatives on the (+)‐ and (−)‐hexahelicen‐7‐yl acetic acid bonded phases
Author(s) -
Del Alamo Aurora,
Grieb Sally,
Tiritan Maria Elizabeth,
Matlin Stephen
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:5/6<416::aid-chir11>3.0.co;2-h
Subject(s) - chemistry , aryl , alkyl , chirality (physics) , enantiomer , acetic acid , alcohol , reagent , side chain , stereochemistry , organic chemistry , medicinal chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark , polymer
This paper describes the synthesis of (+)‐ and (−)‐hexahelicen‐7‐yl acetic acid bonded phases using two bonding reagents. The relationship between the structure of a series of DNB derivatives of chiral aryl alcohols and their enantioselectivity on the (+)‐hexahelicen‐7‐yl acetic acid bonded phase is presented. The DNB derivatives were selected to reflect a range of alkyl side chain lengths, spacer chain lengths between the chiral centre, and the aromatic group and the aromatic group size. The resolution increases with increasing length of the alkyl chain at the chiral centre and decreases on increasing the distance between the aromatic group and the chiral centre. It was confirmed that the enantiomer elution order reverses when changing from the (+)‐ to the (−)‐hexahelicene phase. Chirality 11:416–419, 1999. © 1999 Wiley‐Liss, Inc.