Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

H. Q. Nimal Gunaratne A , Tiina Laaksonen B , Kenneth R. Seddon A and Kristiina Wähälä B C D
+ Author Affiliations
- Author Affiliations

A QUILL Research Centre, School of Chemistry and Chemical Engineering, The Queen’s University of Belfast, Belfast BT9 5AG, Northern Ireland, UK.

B Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, PO Box 55, FI-00014 University of Helsinki, Finland.

C Medicum, PO Box 21, FI-000140 University of Helsinki, Finland.

D Corresponding author. Email: kristiina.wahala@helsinki.fi

Australian Journal of Chemistry 70(7) 845-856 https://doi.org/10.1071/CH16545
Submitted: 27 September 2016  Accepted: 3 February 2017   Published: 8 March 2017

Abstract

Nine new (+)-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 non-aromatic α-substituted carboxylic acids.


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