The interconverting enantiomers of axially chiral 1-naphthamides have been resolved by HPLC on the Whelk-O1 chiral stationary phase, at temps. ranging from +50 to -60. For each compd., a combination of eluent flow rate and column temp. was chosen to generate exchange-broadened chromatog. profiles. Computer simulation of these profiles gave the rate consts. for the on-column R-S interconversion process, occurring by CAr-CO bond rotation. For one 1-naphthamide with different N-alkyl substituents, both CAr-CO and CO-N rotations were detected by low temp. HPLC on the same chiral stationary phase.
Chromatographic resolution and enantiomerization barriers of axially chiral 1-naphthamides / Gasparrini, Francesco; D'Acquarica, Ilaria; Pierini, Marco; Villani, Claudio. - In: JOURNAL OF SEPARATION SCIENCE. - ISSN 1615-9306. - STAMPA. - 24:(2001), pp. 941-946. [10.1002/1615-9314(20011201)24:12<941::AID-JSSC941>3.0.CO;2-V]
Chromatographic resolution and enantiomerization barriers of axially chiral 1-naphthamides
GASPARRINI, Francesco;D'ACQUARICA, Ilaria;PIERINI, MARCO;VILLANI, Claudio
2001
Abstract
The interconverting enantiomers of axially chiral 1-naphthamides have been resolved by HPLC on the Whelk-O1 chiral stationary phase, at temps. ranging from +50 to -60. For each compd., a combination of eluent flow rate and column temp. was chosen to generate exchange-broadened chromatog. profiles. Computer simulation of these profiles gave the rate consts. for the on-column R-S interconversion process, occurring by CAr-CO bond rotation. For one 1-naphthamide with different N-alkyl substituents, both CAr-CO and CO-N rotations were detected by low temp. HPLC on the same chiral stationary phase.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
