Resolution of enantiomers of 2,2,2-trifluoro-1-(9-anthryl)ethanol on cellulose, triphenylcarbamate as chiral stationary phase

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-1-(9-anthryl) ethanol enantiomers on chiral stationary phase (CSP) was investigated. The chiral recognition mechanism for die 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 interaction on;(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.