ISSN:
0899-0042
Keywords:
chiral separation
;
chiral selector
;
separation of enantiomers
;
liquid chromatography
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A chiral stationary phase (CSP 1) prepared starting from (R)-4-hydroxyphenylglycine and then grafting (R)-N-butanoyl-4-allyloxyphenylglycine N-propyl amide to silica gel was found to be very effective in separating the enantiomers of N-(3,5-dinitrobenzoyl)-α-amino amides. From the chromatographic behaviors of the resolution of N-propyl amides, N,N-diethyl amides and ethyl esters of N-(3,5-dinitrobenzoyl)-α-amino acids and the resolution of various N-(substituted benzoyl)leucine N-propyl amides, the hydrogen bonding and the π-π donor-acceptor sites of the analyte for the interaction with the CSP have been proposed. Similarly, the hydrogen bonding donor and acceptor sites of the CSP for the interaction with the analyte have been proposed from the comparison of the chromatographic behaviors of the resolution of various N-(3,5-dinitrobenzoyl)-α-amino N-propyl amides on modified CSPs (CSP 7 containing trifluoroacetyl group instead of the butanoyl group of CSP 1 and CSP 8 containing N,N-diethyl group instead of the N-propyl group of CSP 1) with those on CSP 1. By correlating the interaction sites of the CSP and their complementary interaction sites of the analyte, a chiral recognition mechanism which utilizes the two hydrogen bonding interactions and the π-π donor-acceptor interaction between (R)-CSP 1 and more retained analytes, (S)-N-(3,5-dinitrobenzoyl)-α-amino amides, has been proposed. Chirality 10:592-599, 1998. © 1998 Wiley-Liss, Inc.
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
