Premium
Chromatographic resolution and enantiomerization barriers of axially chiral 1‐naphthamides
Author(s) -
Gasparrini Francesco,
D'Acquarica Ilaria,
Pierini Marco,
Villani Claudio
Publication year - 2001
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/1615-9314(20011201)24:12<941::aid-jssc941>3.0.co;2-v
Subject(s) - enantiomer , chemistry , chiral stationary phase , chiral column chromatography , chromatography , axial symmetry , alkyl , resolution (logic) , high performance liquid chromatography , column chromatography , volumetric flow rate , phase (matter) , packed bed , atropisomer , analytical chemistry (journal) , organic chemistry , thermodynamics , physics , structural engineering , artificial intelligence , computer science , engineering
The interconverting enantiomers of axially chiral 1‐Naphthamides have been resolved by HPLC on the Whelk‐O1 chiral stationary phase, at temperatures ranging from +50°C to –60°C. For each compound, a combination of eluent flow rate and column temperature was chosen to generate exchange‐broadened chromatographic profiles. Computer simulation of these profiles gave the rate constants for the on‐column R‐S interconversion process, occurring by C Ar —CO bond rotation. For one 1‐naphthamide with different N ‐alkyl substituents, both C Ar —CO and CO—N rotations were detected by low temperature HPLC on the same chiral stationary phase.