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Synthesis and Enantioseparation Ability of Xylan Bisphenylcarbamate Derivatives as Chiral Stationary Phases in HPLC
Author(s) -
Li Geng,
Shen Jun,
Li Qiang,
Okamoto Yoshio
Publication year - 2015
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.22472
Subject(s) - chemistry , xylan , high performance liquid chromatography , cellulose , chiral column chromatography , organic chemistry , chirality (physics) , chiral derivatizing agent , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Ten novel xylan bisphenylcarbamate derivatives bearing meta ‐ and para ‐substituents on their phenyl groups were synthesized and their chiral recognition abilities were evaluated as the chiral stationary phases (CSPs) for high‐performance liquid chromatography (HPLC) after coating them on macroporous silica. The chiral recognition abilities of these CSPs depended on the nature, position, and number of the substituents on the phenyl moieties. The introduction of an electron‐donating group was more attractive than an electron‐withdrawing group to improve the chiral recognition ability of the xylan phenylcarbamate derivatives. Among the CSPs discussed in this study, xylan bis(3,5‐dimethylphenylcarbamate)‐based CSP seems to possess the highest resolving power for many racemates, and the meta ‐substituted CSPs showed relatively better chiral recognition than the para ‐substituted ones. For some racemates, the xylan bis(3,5‐dimethylphenylcarbamate) derivative exhibited higher enantioselectivity than the CSP based on cellulose tris(3,5‐dimethylphenylcarbamate). Chirality 27:518–522, 2015 © 2015 Wiley Periodicals, Inc.