Nine new (þ)-dehydroabietylimidazolium salts were synthesised and studied as chiral solvating agents for several different racemic aromatic and non-aromatic carboxylate salts. These cationic chiral solvating agents resolve racemic ionic analytes better than non-ionic ones. Bis(dehydroabietylimidazolium) bis(trifluoromethanesulfonimide) gave the best discrimination for the enantiomers of carboxylate salts. Its resolution behaviour was studied by an NMR titration experiment, which indicated 1 : 1 complexation with the racemic analyte. The dehydroabietylimidazolium salts were also useful in enantiomeric excess (ee) determinations, and for the recognition of chirality of racemic aromatic and nonaromatic a-substituted carboxylic acids.
Gunaratne, H. Q. N., Laaksonen, T., Seddon, K. R., & Wähälä, K. (2017). 1‐(+)‐Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy. Australian Journal of Chemistry, 70(7). https://doi.org/10.1071/CH16545