Enantiomer self-disproportionation of chiral compounds on achiral ordered mesoporous silica M41S and regular silica gel as a stationary phase.
Chromatographic behavior of nonracemic mixtures, viz., mandelic acid and stilbene oxide as analytes has been studied in detailed by enantiomer self-disproportionation on achiral ordered mesoporous material M41S and regular silica gel as stationary phases. Enantiomer self-disproportionation gave enhanced separation of analytes. The extent and magnitude of enantiomer self-disproportionation is dependent on the optical purity of the starting non-racemic molecules, presence of intermolecular hydrogen bonding/pi-pi interactions and the nature of eluents used. The present study and previous literature data suggest that percentage ee of a nonracemic mixture needs to be determined before any chromatographic purification is taken up as enantiomer self-disproportionation phenomenon could occur during purification. The data show that enantiomer self-disproportionation of nonracemic mixtures can be harnessed for its enantioenrichment on inexpensive achiral stationary phases.
Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute (CSMCRI), Bhavnagar, Gujarat, India.
V J
VJ
Mayani
S H R
SH
Abdi
R I
RI
Kureshy
N H
NH
Khan
S
S
Agrawal
R V
RV
Jasra
D002850:Chromatography, Gel / Q000379:methods*; D006860:Hydrogen Bonding; D008333:Mandelic Acids / Q000032:analysis / Q000302:isolation & purification; D016062:Porosity; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000032:analysis / Q000302:isolation & purification; D013499:Surface Properties; D013696:Temperature
D008333:Mandelic Acids; D012997:Solvents; D013267:Stilbenes; D058428:Silica Gel; D012822:Silicon Dioxide; C025906:stilbene oxide; C037938:mandelic acid