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  • Solvent effect in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on a polysaccharide-based chiral stationary phase.

Solvent effect in the chromatographic enantioseparation of 1,1'-bi-2-naphthol on a polysaccharide-based chiral stationary phase.

Journal of chromatography. A (2010-05-15)
Fengping Zhan, Guangyan Yu, Bixia Yao, Xueping Guo, Ting Liang, Minggen Yu, Qingle Zeng, Wen Weng
RESUMEN

Enantioseparation of 1,1'-bi-2-naphthol (BINOL) was performed on a polysaccharide-based chiral stationary phase, Chiralcel OD-H, under normal-phase mode. The effects of polar modifier in the mobile phase on the retention, enantioseparation and elution order were investigated in detail. Solvent-induced reversal of elution order for BINOL was observed. When linear alcohols were adopted, R-BINOL was always eluted first. S-BINOL was eluted first when 2-propanol was used as a polar modifier. Enantioseparation could not be obtained when sec-butyl alcohol or tert-butyl alcohol was used as a polar modifier. When isoamyl alcohol or cyclohexanol was used as a polar modifier, favorable enantioseparation was obtained as with 1-pentanol or 1-hexanol; also, R-BINOL was the first-eluted enantiomer. It is worth emphasizing that significantly better enantioseparation was obtained when higher alcohols were used as polar modifier of the mobile phase. A nonlinear characteristic for the lnalpha against 1/T plots was universally observed in this study though the lnk against 1/T plots exhibited a linear feature. Associated with the obtained thermodynamic parameters, some interesting inferences about chiral recognition mechanism were proposed.

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1,1′-Bi-2-naphthol, 99%