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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
引用本文:王来来,吕士杰,高平,夏春谷,李树本.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[J].分析化学,1999,27(7):828-831.
作者姓名:王来来  吕士杰  高平  夏春谷  李树本
作者单位:中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,兰州,730000
摘    要:用高效液相色谱法在涂敷15%(Wt)三苯基氨基甲酸纤维素醌手性柱上,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,还与洗脱中醇改变固定相中手性空穴的立体环境有关,

关 键 词:三苯基氨基甲酸纤维素酯  手性柱  对映体拆分  高效液相色谱法

Resolution of Enantiomers of 2,2,2-Trifluoro-1- ( 9-anthryl ) ethanol on Cellulose Triphenylcarbamate as Chiral Stationary Phase
Wang Lailai,L Shijie,Gao Ping,XIA Chungu,LI Shuben.Resolution of Enantiomers of 2,2,2-Trifluoro-1- ( 9-anthryl ) ethanol on Cellulose Triphenylcarbamate as Chiral Stationary Phase[J].Chinese Journal of Analytical Chemistry,1999,27(7):828-831.
Authors:Wang Lailai  L Shijie  Gao Ping  XIA Chungu  LI Shuben
Institution:Wang Lailai,L(u) Shijie,Gao Ping,XIA Chungu,LI Shuben
Abstract: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.
Keywords:Cellulose triphenylcarbamate  chiral column  resolution of enantiomers  high performance liquid chromatography
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