| Enantiomer separation is one of the most important research fields of chiral technology. High performance liquid chromatographic (HPLC) separation of enantiomers on chiral stationary phases (CSPs) has been known as the most accurate and convenient means in determining the enantiomeric purity and preparing the chiral compounds. The Pirkle-Type CSPs, on which many chiral compounds can be separated, are important in various fields.In this thesis, two amide derivative chiral selectors of Brush-Type CSPs, 5-(10-undecenylpropylamido) acenaphthene and 5-(1-(3, 5-dinitrobenzoylamino) pent-4-enyl) acenaphthene, have been synthesized. Both reaction and purification conditions were studied to get a better recovery. The enantiomeric separation of 5-(10-undecenylpropylamido) acenaphthene and 5-(1-(3, 5-dinitrobenzoylamino) pent-4-enyl) acenaphthene by HPLC on several chiral stationary phases, such as DNB-Leucine CSP, DNB-PG CSP, Whelk-O1 CSPand SH-1 CSP, were studied. The results showed that separation conditions of 5-(10-undecenylpropylamido) acenaphth-ene by HPLC on DNB-Leucine CSP, DNB-PG CSP, and Whelk-O1 CSP were better, and separation conditions of 5-(1-(3, 5-dinitrobenzoylamino) pent-4-enyl) acenaph-thene on DNB-Leucine CSP, DNB-PG CSP, and SH-1 CSP were better. The optimium conditions of the separation were investigated, which could be taken as an important reference for preparative chiral liquid chromatography. Based on these results, the hypothetical chiral recognition mechanism was discussed. These chiral selectors were detected by Photo-Diode-Array detector and Optical-Rotation detector of high performance liquid chromatography. The method separated the racemate is established, and this is useful for further study of chiral separation mechanism.(R)-2-thiothiazolidine-4-carboxylic acid is one of the chiral resolutive reagents, and can separate the racemates, such as amino acyl esters, amino alcohol, and phenylethylamine and so on. The direct separation of the racemate, 2-thiothiazolidine-4-carboxylic acid, by high performance liquid chromatography is unrecorded. As the useful chiral separation reagents, it is unfeasible that the special rotation is just noted, but the enantiomeric purity is not reported. This can influence on its synthetic optimization, and prevent its applications. In this thesis, the direct separation conditions of the racemate of 2-thiothiazolidine-4-carboxylic acid on DNB-Leucine CSP, DNB-PG CSP, Whelk-O1 CSP and OD-H CSP were studied, but failed. The 2-thiothiazolidine-4-carboxylic acid was derivatized with aniline which was the reagent of pre-column derivatization of high performance liquid chromatography. The derivative was separated by DNB-Leucine chiral stationary phase, and detected by Photo-Diode-Array detector and Optical-Rotation detector. The method which separated the racemate and determined the enantiomeric purity of 2-thiothiazolidine-4-carboxylic acid was established. Chromatographic model was employed for enantionmeric separation of 2-thiothiazolidine-4-carboxylic acid derivatives on the DNB-Leucine chiral column in hexane/alcohol (ethanol or isopropyl alcohol) mobile phase. The effects of chromatography conditions, such as mobile phases and temperature to chiral recognition, had been investigated. A better condition of analysis was obtained, and the separation factor was more than 1.2. Furthermore, the results of enantiomeric purity determined by polarimeter and HPLC were very consistent, and the relative deviation was not more than 1.34ï¼…. The method of pre-column derivatization of high performance liquid chromatography is credible, accurate and can be applied to determine enantiomeric purity of 2-thiothiazolidine-4-carboxylic acid. The effects of concentration and temperature on special rotation of (R)-2-thiothiazolidine-4-carboxylic acid were studied. From 0.50 to 1.50 g/100mL, the concentration had little influence on its special rotation. The temperature had no influence on its special rotation. The method of determining the enantiomeric purity and special rotation is established. It is significative of exploitation and applications of the novel chiral resolutive reagent (R)-2-thiothiazolidine-4-carboxylic acid.
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