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.
Mayani
V J
VJ
Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute (CSMCRI), Bhavnagar, Gujarat, India.
Abdi
S H R
SH
Kureshy
R I
RI
Khan
N H
NH
Agrawal
S
S
Jasra
R V
RV
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