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Homogeneous synthesis of partially substituted cellulose phenylcarbamates aiming at chiral recognition.
- Source :
- Polymer International; Aug2015, Vol. 64 Issue 8, p1037-1044, 8p
- Publication Year :
- 2015
-
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 andmolar 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- CELLULOSE
IONIC liquids
SUBSTITUTION reactions
CHIRAL recognition
ISOCYANATES
Subjects
Details
- Language :
- English
- ISSN :
- 09598103
- Volume :
- 64
- Issue :
- 8
- Database :
- Complementary Index
- Journal :
- Polymer International
- Publication Type :
- Academic Journal
- Accession number :
- 108796300
- Full Text :
- https://doi.org/10.1002/pi.4884