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Issue 11, 2008
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Ionic liquid characteristics of 1-alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl)pyridinium salts

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Abstract

1-Alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl)pyridinium salts have been synthesised and characterised in order to compare the effects of different electron-withdrawing functional groups on their ability to form ionic liquids. The presence of the electron-withdrawing nitrile or trifluoromethyl substituent on the pyridinium ring leads to salts with higher melting points than with the corresponding 1-alkylpyridinium or 1-alkylpicolinium cations. Solid-state structures were determined by single crystal X-ray crystallography for seven salts; 1-methyl-4-cyanopyridinium methylsulfate, and 1-methyl-3-cyanopyridinium, 1-methyl-4-cyanopyridinium, 1-ethyl-2-cyanopyridinium, 1-ethyl-3-cyanopyridinium, 1-ethyl-4-cyanopyridinium and 1-ethyl-4-(trifluormethyl)pyridinium bis{(trifluoromethyl)sulfonyl}imide, and show the effects of ring-substitution position on hydrogen-bonding in the solid-state and on melting points.

Graphical abstract: Ionic liquid characteristics of 1-alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl)pyridinium salts

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Article information


Submitted
26 Mar 2008
Accepted
30 May 2008
First published
18 Jul 2008

New J. Chem., 2008,32, 1953-1967
Article type
Paper

Ionic liquid characteristics of 1-alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl)pyridinium salts

C. Hardacre, J. D. Holbrey, C. L. Mullan, M. Nieuwenhuyzen, W. M. Reichert, K. R. Seddon and S. J. Teat, New J. Chem., 2008, 32, 1953
DOI: 10.1039/B805063E

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