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Abstract
A new liquid chromatographic chiral stationary phase (CSP) was prepared by bonding N-(3,5-dimethoxybenzoyl)cefaclor to spherical silica gel. The new CSP was successfully utilized for the resolution of racemic N-(3,5-dinitrobenzoyl)-α-amino acid derivatives and racemic 3-substituted 1,4-benzodiazepin-2-ones. For the resolution of racemic N-(3,5-dinitrobenzoyl)-α-amino acid derivatives on the CSP, a chiral recognition mechanism utilizing the enantioselective π−π donor–acceptor interaction between the π-basic 3,5-dimethoxybenzoyl group of the CSP and the π-acidic 3,5-dinitrobenzoyl group of analytes was proposed.
ACKNOWLEDGMENTS
This work was supported by a grant-in-aid for the National Core Research Center Program from MEST and KOSEF (R15-2006-022-03001-0).
Manuscript 6427
Notes
a Mobile phase: 20% isopropyl alcohol in hexane. Flow rate: 1.0 mL/min. Detection: 254 nm UV. Temperature: 20°C. k 1: Retention factor of the first eluted enantiomer. The absolute configuration of the first eluted enantiomer is presented in the parenthesis. k 2: Retention factor of the second eluted enantiomer. The absolute configuration of the second eluted enantiomer is presented in the parenthesis. α: Separation factor.
a Mobile phase: 20% ethyl alcohol in hexane. Flow rate: 1.0 mL/min. Detection: 254 nm UV. Temperature: 20°C. k 1: Retention factor of the first eluted enantiomer. The absolute configuration of the first eluted enantiomer is presented in the parenthesis. k 2: Retention factor of the second eluted enantiomer. The absolute configuration of the second eluted enantiomer is presented in the parenthesis. α: Separation factor.
a Mobile phase: 20% ethyl alcohol in hexane. Flow rate: 1.0 mL/min. Detection: 254 nm UV. Temperature: 20°C. k 1: Retention factor of the first eluted enantiomer. The absolute configuration of the first eluted enantiomer is presented in the parenthesis. k 2: Retention factor of the second eluted enantiomer. The absolute configuration of the second eluted enantiomer is presented in the parenthesis. α: Separation factor.
a Mobile phase: 20% isopropyl alcohol in hexane. Flow rate: 1.0 mL/min. Detection: 254 nm UV. Temperature: 20°C. k 1: Retention factor of the first eluted enantiomer. The absolute configuration of the first eluted enantiomer is presented in the parenthesis. k 2: Retention factor of the second eluted enantiomer. The absolute configuration of the second eluted enantiomer is presented in the parenthesis. α: Separation factor.