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A Practical Solvating Agent for the Chiral NMR Discrimination of Carboxylic Acids
Author(s) -
Kim Seonmi,
Choi Kihang
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100692
Subject(s) - chemistry , enantiomer , reagent , carboxylic acid , chiral derivatizing agent , organic chemistry , chemical shift , combinatorial chemistry , computational chemistry , chiral column chromatography
A bisimidazoline compound has been prepared as a new chiral solvating agent starting from isophthalaldehyde and ( S , S )‐1,2‐diphenylethylenediamine through a single‐step synthesis. In the presence of one equivalent of this reagent, carboxylic acid racemates show 1 H NMR chemical shift nonequivalences large enough for the discrimination of the enantiomers. Studies with related compounds showed that the 1,3‐disubstituted structure is crucial for the acid‐solvating ability of the bisimidazoline compound.