2,2,2-三氟-1-(9-蒽基)乙醇对映体在涂敷型手性固定相上的拆分

Resolution of Enantiomers of 2,2,2-Trifluoro-1-(9-anthryl)ethanol on Cellulose Triphenylcarbamate as Chiral Stationary Phase

用高效液相色谱法在涂敷15%(Wt)三苯基氨基甲酸纤维素酯手性柱上,考察了洗脱液正己烷/醇(V/V)中醇对分离(±)-2,2,2-三氟-1-(9-蒽基)乙醇对映体的影响,初步认为,在对映体分离过程中,洗脱液中的醇与手性固定相的NH和C=O形成氢键作用,此过程与对映体和手性固定相的NH和C=O所形成氢键作用相竞争;洗脱液中醇的结构不同之所以影响对映体的分离效果,还与洗脱液中醇改变固定相中手性空穴的立体环境有关,醇的结构不同,造成固定相中手性空穴的立体环境不同.

Series of primary and secondary alcohols (ethanol, 1-propanol, 2-propanol, 1-butanol, iso-butyl alcohol, 1-pentanol) were used as the mobile phase component, respectively. The effect of these alcohols on the capacity factor and stereoselectivity of 2,2,2-trifluoro-l-(9-anthryl)ethanol enantiomers on chiral stationary phase (CSP) was investigated. The chiral recognition mechanism for the enantiomers may involve, (1) The aromatic portion of enantiomers may insert into a chiral cavity of the CSP via hydrogen bonding with the enantiomers's alcoholic hydrogen and NH and C = O groups on the CSP and the dipole-dipole interactionon ;(2)The various alcohols compete with the enantiomers for chiral, as well as achiral, binding sites on the CSP; The structure of .the various alcohols has some effect on stereoselectivity through an alteration of the steric environment of the chiral cavity.