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

Christopher Hardacre, John Holbrey, Claire Mullan, Mark Nieuwenhuyzen, W.M. Reichert, Kenneth Seddon, S.J. Teat

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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.
Original languageEnglish
Pages (from-to)1953-1967
Number of pages15
JournalNew journal of chemistry
Volume32
Issue number11
DOIs
Publication statusPublished - 2008

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Hardacre, C., Holbrey, J., Mullan, C., Nieuwenhuyzen, M., Reichert, W. M., Seddon, K., & Teat, S. J. (2008). Ionic liquid characteristics of 1-alkyl-n-cyanopyridinium and 1-alkyl-n-(trifluoromethyl) pyridinium salts. New journal of chemistry, 32(11), 1953-1967. https://doi.org/10.1039/b805063e