Different enantioselective interaction pathways induced by derivatized quinines.
The stereochemistries in solution of the diastereoisomeric complexes formed by quinines modified at the hydroxyl site (9-O-acetylquinine; 9-O-(3,5-dimethoxyphenylcarbamate)quinine) or quinuclidine nitrogen (N-benzylquininium chloride) and each enantiomer of 2-(3', 5'-dinitrobenzamido)-1-phenylethanol have been compared to those of the free compounds by (1)H NMR investigations. Completely different interaction models, also involving changes of the free state conformations, have been obtained.
Uccello-Barretta
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G
Centro di Studio del CNR per le Macromolecole Stereordinate ed Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, via Risorgimento 35, 56126 Pisa, Italy.
Balzano
F
F
Quintavalli
C
C
Salvadori
P
P
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011803:Quinine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012996:Solutions; D013237:Stereoisomerism
D007202:Indicators and Reagents; C572719:N-benzylquininium; D012996:Solutions; D011803:Quinine