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Synthesis and hplc chiral recognition of regioselectively carbamoylated cellulose derivatives
Author(s) -
Tang Shouwan,
Li Xiaofang,
Wang Fang,
Liu Guihua,
Li Yonglong,
Pan Fuyou
Publication year - 2012
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.21978
Subject(s) - chemistry , regioselectivity , cellulose , chirality (physics) , derivative (finance) , high performance liquid chromatography , organic chemistry , chromatography , catalysis , physics , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark , chiral symmetry breaking
Abstract Four regioselective‐carbamoylated cellulose derivatives having two different substituents at 2‐, 3‐, and 6‐position were prepared and evaluated as chiral stationary phases (CSPs) for high‐performance liquid chromatography. Investigations showed that the nature andarrangement of the substituents significantly influenced the chiral recognition abilities of the heterosubstituted cellulose derivatives and each derivative exhibited characteristic enantioseparation. Some racemates were better resolved on these derivatives than the corresponding homogeneously substituted cellulose derivatives including a commercial CSP, Chiralcel OD. Racemic compounds shown in this study were most effectively discriminated on cellulose2,3‐(3‐chloro‐4‐methylphenylcarbamate)‐6‐(3,5‐dimethylphenylcarbamate) and 2,3‐(3,5‐dimethylphenylcarbamate)‐6‐(3‐chloro‐4‐methylphenylcarbamate). Chirality, 2012. © 2011 Wiley Periodicals, Inc.