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Chiral recognition mechanism study of mandelic acid on whelk O1 column with pre-column derivatization

Hao Zeng, Yiwen Zhang, Shun Yao, Hang Song

The mandelic acid was derivatized with four amines and the derivatives were resolved on four types of chiral columns. The results indicated that phenethylamine derivative was resolved well on all the four columns and the Whelk O1 column had the best resolution. The resolution of phenethylamine derivative on Whelk O1 column was then validated before the mechanismstudy. The influence of temperature on chiral recognition of phenethylamine derivative had been investigated on Whelk O1 column. By analyzing thermodynamic data of chiral separation process, the mechanism of chiral separation was tentatively investigated. The results suggested that the separation was mainly controlled by steric hindrance, and it was an enthalpy-driven course. Chromatographic model was employed for enantionmeric separation of mandelic acid derivatives onWhelk O1 column using hexane/ethanol mobile phase.