Published:Journal of Chromatographic Science,
ISSN 0021-9665Volume
39, Number 9, September 2001, pp. 388-392
Chiral
Separation of Glycidyl Selenide and Glycidyl Sulfide Racemates on Cellulose-Based
Chiral Stationary Phases
Jing-Guo
Hou1, Xiao-Qian Han[1], Hui-Tao Liu[2], Ya-li Wang, and Jin-Zhang Gao[1]
[1]Institute of Chemistry, Northwest Normal University, Lanzhou 730070, China
and [2]Department of Chemistry,
Lanzhou University 730000, China
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 þ–þ 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.
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