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Homogeneous synthesis of partially substituted cellulose phenylcarbamates aiming at chiral recognition
Author(s) -
Chen Weiwei,
Zhang Mei,
Feng Ye,
Wu Jin,
Gao Xia,
Zhang Jinming,
He Jiasong,
Zhang Jun
Publication year - 2015
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.4884
Subject(s) - reactivity (psychology) , cellulose , substituent , chemistry , organic chemistry , isocyanate , ionic liquid , electronic effect , catalysis , medicinal chemistry , medicine , alternative medicine , pathology , polyurethane
Abstract Homogeneous carbanilation of cellulose with nine kinds of substituted phenyl isocyanates, in which the substituents were varied from electron‐donating to electron‐withdrawing groups, was carried out in 1‐allyl‐3‐methylimidazolium chloride ( AmimCl ) without any catalyst. The degree of substitution ( DS ) of cellulose phenylcarbamates in a range from 0 to 3 was readily controlled by altering reaction temperature, reaction time and molar ratio of phenyl isocyanate/anhydroglucose unit. Furthermore, the electronic effect of the substituents on the aromatic ring had a prominent impact on the reactivity of phenyl isocyanates. The phenyl isocyanates with stronger electron‐withdrawing substituents exhibited a higher reactivity. A plot of DS and Hammett substituent constants exhibited linearity with a positive slope. Subsequently, four kinds of partially substituted cellulose phenylcarbamates with DS of 2.0 were synthesized successfully in AmimCl , and then employed as coated‐type chiral stationary phases ( CSPs ) for high‐performance liquid chromatography. The enantioseparation results demonstrated that these CSPs exhibited high chiral recognition abilities for some racemates. The substituents on the phenyl moieties had a considerable effect on the chiral recognition ability of cellulose phenylcarbamate‐based CSPs . © 2015 Society of Chemical Industry