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Issue 12, 2013
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Noncovalent interactions in halogenated ionic liquids: theoretical study and crystallographic implications

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Abstract

In recent years, several specific imidazolium-based ionic liquids with halogen substituents on the imidazole ring as well as on the alkyl chains have been reported. In this work, noncovalent interactions in four halogenated ionic liquids, i.e. 2-bromo-/iodo- and 4,5-dibromo-/diiodo-1,3-dimethylimidazolium trifluoromethanesulfonates, were systematically investigated using density functional theory calculations. The structural and energetic properties of the ion pairs for such ionic liquids have been fully examined and compared with the non-halogenated ones. It was found that C–X⋯O halogen bonds, C–H⋯O hydrogen bonds, and electrostatic interactions with the anion located over the imidazole ring in the ion pairs. In addition, the structures and energetics of two ion pairs for such ionic liquids were also explored to reproduce experimental observations. The halogen-bonded ring structures and the conformers with the concurrent C–H⋯O and C–X⋯O contacts were predicted, consistent with the X-ray crystal structures of corresponding organic salts. Finally, the implications of the observed structural and energetic features of ion pairs on the design of halogen-bonding ionic liquids were discussed. The results presented herein should provide useful information in the development of novel halogenated ionic liquids used for specific tasks ranging from organic synthesis to gas absorption.

Graphical abstract: Noncovalent interactions in halogenated ionic liquids: theoretical study and crystallographic implications

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Publication details

The article was received on 22 Dec 2012, accepted on 23 Jan 2013 and first published on 28 Jan 2013


Article type: Paper
DOI: 10.1039/C3CP44649B
Citation: Phys. Chem. Chem. Phys., 2013,15, 4405-4414
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    Noncovalent interactions in halogenated ionic liquids: theoretical study and crystallographic implications

    H. Li, Y. Lu, W. Wu, Y. Liu, C. Peng, H. Liu and W. Zhu, Phys. Chem. Chem. Phys., 2013, 15, 4405
    DOI: 10.1039/C3CP44649B

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