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A Theoretical and Experimental Chemist’s Joint View on Hydrogen Bonding in Ionic Liquids and Their Binary Mixtures

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Electronic Effects in Organic Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 351))

Abstract

A combined experimental and theoretical approach including quantum chemistry tools and computational simulation techniques can provide a holistic description of the nature of the interactions present in ionic liquid media. The nature of hydrogen bonding in ionic liquids is an especially intriguing aspect, and it is affected by all types of interactions occurring in this media. Overall, these interactions represent a delicate balance of forces that influence the structure and dynamics, and hence the properties of ionic liquids. An understanding of the fundamental principles can be achieved only by a combination of computations and experimental work. In this contribution we show recent results shedding light on the nature of hydrogen bonding, for certain cases the formation of a three-dimensional network of hydrogen bonding, and its dynamics by comparing 1-ethyl-3-methylimidazolium based acetate, chloride and thiocyanate ionic liquids.

A particularly interesting case to study hydrogen bonding and other interactions is the investigation of binary mixtures of ionic liquids of the type [cation1][anion1]/[cation1][anion2]. In these mixtures, competing interactions are to be expected. We present both a thorough property meta-analysis of the literature and new data covering a wide range of anions, i.e., mixtures of 1-ethyl-3-methylimidazolium acetate with either trifluoroacetate, tetrafluoroborate, methanesulfonate, or bis(trifluoromethanesulfonyl)imide. In most cases, ideal mixing behavior is found, a surprising result considering the multitude of interactions present. However, ideal mixing behavior allows for the prediction of properties such as density, refractive index, surface tension, and, in most cases, viscosity as function of molar composition. Furthermore, we show that the prediction of properties such as the density of binary ionic liquid mixtures is possible by making use of group contribution methods which were originally developed for less complex non-ionic molecules. Notwithstanding this ideal mixing behavior, several exciting applications are discussed where preferential solvation via hydrogen bonding gives rise to non-additive effects leading to performance improvements. The assessment of the excess properties and 1H NMR spectroscopic studies provide information on these structural changes and preferential interactions occurring in binary mixtures of ionic liquid, that clearly support the conclusions drawn from the computational studies.

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Abbreviations

[C n mim]+ :

1-Alkyl-3-methylimidazolium cation

[C n mpy]+ :

N-Alkyl-3-methylpyridinium cation

[C n mpyr]+ :

N-Alkyl-N-methylpyrrolidinium cation

[EtNH3]+ :

Ethylammonium cation

[NTf2]− :

Bis(trifluoromethanesulfonyl)imide anion

[OAc]− :

Acetate anion

[SCN]− :

Thiocyanate anion

AIMD:

Ab initio molecular dynamics

CDF:

Combined distribution function

DFT:

Density functional theory

IR:

Infra red

MD:

Molecular dynamics

MP2:

Møller–Plesset perturbation theory

NMR:

Nuclear magnetic resonance

u:

Uncertainty

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Acknowledgments

This work was supported by the DFG, in particular by the projects KI-768/4-1 and KI-768/4-2 from the ERA-chemistry, KI-768/5-2, KI-768/5-3, STA-1027/2-1, STA-1027/2-2, and STA-1027/2-3 from the priority program on ionic liquids (SPP 1191). The participation of ASP was made possible by a postdoctoral fellowship granted by the DFG through SPP 1191. Computer time from the RZ Leipzig is gratefully acknowledged. Likewise, we would like to thank M. Ramzan, M. Reichelt, H. Rudzik, A. Foerster, C. Birkemeyer, and L. Hennig for experimental support. Figures 3, 4, 5 and 6 were visualised using TRAVIS [131].

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Authors and Affiliations

  1. Institute for Chemical Technology, Universität Leipzig, Linnéstr. 3-4, 04103, Leipzig, Germany

    Annegret Stark

  2. Wilhelm-Ostwald-Institute for Physical and Theoretical Chemistry, Universität Leipzig, Linnéstr. 2, 04103, Leipzig, Germany

    Martin Brehm, Marc Brüssel, Sebastian B. C. Lehmann, Alfonso S. Pensado & Matthias Schöppke

  3. Mulliken Center for Theoretical Chemistry, Institute for Physical and Theoretical Chemistry, Universität Bonn, Beringstr. 4+6, 53115, Bonn, Germany

    Alfonso S. Pensado & Barbara Kirchner

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  1. Annegret Stark
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  1. Universität Bonn, Institut für Physikalische und Theoretische Chemie, Bonn

    Barbara Kirchner

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Stark, A. et al. (2013). A Theoretical and Experimental Chemist’s Joint View on Hydrogen Bonding in Ionic Liquids and Their Binary Mixtures. In: Kirchner, B. (eds) Electronic Effects in Organic Chemistry. Topics in Current Chemistry, vol 351. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_485

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