Chiral separation of glycidyl selenide and glycidyl sulfide racemates on cellulose-based chiral stationary phases.
In recent years, a growing interest has been paid to glycidyl selenide and glycidyl sulfide racemic compounds for their importance in the life science field. In this study, cellulose-based chiral stationary phases are employed for the separation of glycerin selenium and glycerin sulfur racemates. Most analytes obtain satisfactory separation. In order to optimize the resolution of racemates, mixtures of n-hexane with different alcohols are used as mobile phases. The structural features of these racemic compounds affecting chiral discrimination are discussed in detail. The results in this study suggest that the chiral recognition mechanism for these racemic compounds involve two factors: (a) the substitution residue on a nonchiral atom can play a direct or indirect effect during chiral discrimination and (b) the competition between hydrogen-bonding and pi-pi interaction exists for compounds containing both the hydroxyl and aromatic group at the same time. The two interactions play an opposite role in the chiral discrimination process.
Hou
J G
JG
Institute of Chemistry, Northwest Normal University, Lanzhou, China.
Han
X Q
XQ
Liu
H T
HT
Wang
Y L
YL
Gao
J Z
JZ
D002219:Carbamates; D002482:Cellulose / Q000031:analogs & derivatives; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005990:Glycerol / Q000737:chemistry / Q000302:isolation & purification*; D006860:Hydrogen Bonding; D048448:Phenylcarbamates; D018036:Selenium Compounds / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry / Q000302:isolation & purification*
D002219:Carbamates; D048448:Phenylcarbamates; D018036:Selenium Compounds; D013440:Sulfides; C065943:cellulose tris-3,5-dimethylphenyl-carbamate; D002482:Cellulose; D005990:Glycerol