Comparison of 1-(1-naphthyl)ethylcarbamate derivatives of a carbohydrate bonded chiral stationary phase.
New chiral stationary bonded phases (CSPs) based on derivatized malto-oligosaccharides are reported. Chiral separations are reported for 3,5-dinitrobenzoyl-derivatized amines and amino acids as well as some 3,5-dinitrophenylcarbamoylated alcohols. These new CSPs incorporate a 1-(1-naphthyl)ethylcarbamate (NEC) moiety which introduces additional stereogenicity and provides a useful probe for investigating chiral recognition. The elution order, when known, was dependent upon the configuration of the NEC substituent; that is, the S enantiomers were retained longest on the S column and the R enantiomers were retained longest on the R column. Elution order from the RS column, when known, was the same as that observed for the S column. In most cases, retention correlated with bonded ligand concentration on the silica substrate. In general, the best enantioselectivities and resolution were obtained on the S column.
Stalcup
A M
AM
Department of Chemistry, University of Hawaii-Manoa, Honolulu 96822, USA.
Williams
K L
KL
D000438:Alcohols / Q000032:analysis; D000588:Amines / Q000032:analysis; D000596:Amino Acids / Q000032:analysis; D002219:Carbamates / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D004952:Esters / Q000032:analysis; D009281:Naphthalenes / Q000737:chemistry*
D000438:Alcohols; D000588:Amines; D000596:Amino Acids; D002219:Carbamates; D002241:Carbohydrates; D004952:Esters; D009281:Naphthalenes