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Performance of brush‐type HPLC chiral stationary phases with tertiary amide in the connecting tether
Author(s) -
Forjan Davorka Moslavac,
Kontrec Darko,
Vinković Vladimir
Publication year - 2006
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/chir.20329
Subject(s) - chemistry , amide , enantiomer , chiral column chromatography , chiral stationary phase , alanine , chirality (physics) , stereochemistry , kinetic resolution , enantioselective synthesis , amino acid , organic chemistry , catalysis , chiral symmetry breaking , quantum mechanics , quark , biochemistry , nambu–jona lasinio model , physics
The replacement of the NH hydrogen of the secondary amide‐tethered Pirkle‐concept N ‐(3,5‐dinitrobenzoyl)‐ L ‐leucine derived chiral stationary phase with various π‐basic or aliphatic groups improved the chiral discrimination ability of new chiral stationary phases, based on the leucine‐ or alanine‐derived chiral selector, for the enantiomers of various racemic neutral analytes with amide functional groups. Retention times decreased while separation and resolution factors increased, thus proving the role of π‐donor aromatic unit as an electron‐rich shield in the front of a silica surface. In general, chiral stationary phase (CSP) 5 with the 3,5‐dimethylphenyl unit showed best performance, while CSP 3 , with phenyl unit, and CSP 7 , with 1‐naphthyl unit in the tertiary amide connecting tether, were less efficient. Chirality, 2006. © 2006 Wiley‐Liss, Inc.