Investigation of brush-type chiral stationary phases based on O,O'-diaroyl tartardiamide and O,O'-bis-(arylcarbamoyl) tartardiamide.
Four chiral organosilanes based on O,O'-dibenzoyl tartardiamide, O,O'-bis-(3,5-dimethylbenzoyl) tartardiamide, O,O'-bis-(phenylcarbamoyl) tartardiamide and O,O'-bis-[(3,5-dimethylphenyl)carbamoyl] tartardiamide were synthesized and immobilized on silica to afford corresponding brush-type chiral stationary phases (CSPs) with well-defined structures. Using 54 compounds containing a wide variety of structures as analytes, the enantioselectivities of the four CSPs were evaluated under normal-phase modes. 3,5-Dimethyl substituent in the aryl group was found to significantly affect the enantioselectivity of CSPs containing aryl ester moieties. Aryl carbamate moieties in CSPs were observed more beneficial for enantioseparation than aryl ester moieties. The additional hydrogen-bond donors (NH) present in the carbamate groups contributed greatly to the enantioselectivity of CSPs, which is contrary to the results that have been found in network-polymeric CSPs.
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, PR China.
Haibo
H
Wu
Shuying
S
Ji
Bing
B
Yang
Hui
H
Yu
Yu
Y
Jin
Yanxiong
Y
Ke
Xinmiao
X
Liang
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D017646:Organosilicon Compounds; D013644:Tartrates; D014230:Triazoles; D012822:Silicon Dioxide