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To study the Pi-Pi interactions between a chiral selector and the enantiomers of an analyte, a Pi- acidic or Pi-basic group would be contained in the molecules of the derivatives of hydantoin-5-acetic acid, so the aromatic amines such as phenylamine, 4methylaniline, 3,5-dimethylaniline and 3-nitroaniline were chosen as derivatization reagents.
The resolution of the 3-nitroaniline derivative of hydantoin-5-acetic acid on the CHIDMB column was the best, but the retention time was too long.
1: the 3-nitroaniline derivative of hydantoin-5-acetic acid, 2: the phenylamine derivative of hydantoin-5-acetic acid, 3: the 4-methylaniline derivative of hydantoin-5-acetic acid, 4: the 3,5-dimethylaniline derivative of hydantoin-5-acetic acid; mobile phase composition on the CHI-DMB column: n-hexane 80%; mobile phase composition on the Chiralcel OD-H column: n-hexane 85%; t 1 : retention time of the first enantiomer; t 2 : retention time of the second enantiomer; Alpha: separation factor; R s : resolution; flow rate: 1.
The type and concentration of organic modifier were found to influence the retention and resolution of the phenylamine and 3-nitroaniline derivatives of hydantoin-5-acetic acid on the CHIDMB column dramatically.
As a compromise between resolution and retention time, 20% isopropanol in n-hexane was found to be an optimum mobile phase for the phenylamine derivative of hydantoin-5-acetic acid, and 40% isopropanol in nhexane was found to be an optimum mobile phase for the 3-nitroaniline derivative of hydantoin-5-acetic acid.
Table-2: Effect of mobile phase composition on selectivity and resolution of the 3-nitroaniline and phenylamine derivatives of hydantoin-5-acetic acid enantiomers.
1: the 3-nitroaniline derivative of hydantoin-5-acetic acid, 2: the phenylamine derivative of hydantoin-5-acetic acid; Alpha : separation factor; R s : resolution; stationary phase: CHI-DMB; flow rate: 1.
These compounds were synthesized by cycloaddition reaction starting from the commercially available 3-nitroanilines 1, benzaldehyde 2, and trans-anethole, according to the literature procedure (Kouznetsov et al.
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