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

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

doi:10.1071/CH16545

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 language	English
Journal	Australian Journal of Chemistry
Volume	70
Issue number	7
DOIs	https://doi.org/10.1071/CH16545
Publication status	Published - 08 Mar 2017

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1‐(+)‐Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy
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title = "1‐(+)‐Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy",

abstract = "Nine new ({\th})-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.",

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AU - Gunaratne, H. Q. Nimal

AU - Laaksonen, Tiina

AU - Seddon, Kenneth R.

AU - Wähälä, Kristiina

PY - 2017/3/8

Y1 - 2017/3/8

N2 - 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.

AB - 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.

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DO - 10.1071/CH16545

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VL - 70

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 7

ER -

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

Abstract

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