1‐(+)‐Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy

H. Q. Nimal Gunaratne, Tiina Laaksonen, Kenneth R. Seddon, Kristiina Wähälä

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Abstract

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.
Original languageEnglish
JournalAustralian Journal of Chemistry
Volume70
Issue number7
DOIs
Publication statusPublished - 08 Mar 2017

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