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Carbene Formation in Ionic Liquids: Spontaneous, Induced, or Prohibited?

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† Mulliken Centre for Theoretical Chemistry, University of Bonn, Beringstraße 4, D-53115 Bonn, Germany
‡ Wilhelm-Ostwald-Institut für Physikalische und Theoretische Chemie, Universität Leipzig, Linnéstraße 2, D-04103 Leipzig, Germany
§ Institut für Chemie, Technische Universität Chemnitz, Strasse der Nationen 62, D-09111 Chemnitz, Germany
∥ Institut für Technische Chemie, Universität Leipzig, Linnéstraße 3-4, D-04103 Leipzig, Germany
*E-mail: O.H., [email protected]; B.K., [email protected]
Cite this: J. Phys. Chem. B 2013, 117, 19, 5898–5907
Publication Date (Web):April 8, 2013
https://doi.org/10.1021/jp4004399
Copyright © 2013 American Chemical Society
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Abstract

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We present a theoretical study of carbene formation from the 1-ethyl-3-methylimidazolium acetate ionic liquid in the absence and presence of CO2 in gas and liquid phase. Although CO2 physisorption constitutes a precursory step of chemisorption (the CO2’s reaction with carbenes, which forms from cations via proton abstraction by anions), it also enables a very stable CO2–anion associate. However, this counteracts the chemical absorption by reducing the basicity of the anion and the electrophilicity of the CO2, which is reflected by charge transfer. Accordingly, the observable carbene formation in the gas phase is hindered in the presence of CO2. In the neat liquid, the carbene formation is also suppressed by the charge screening compared to the case of the gas phase; nevertheless, indications for carbene incidents appear. Interestingly, in the CO2-containing liquid we detect more carbene-like incidents than in the neat one, which is caused by the way CO2 is solvated. Despite the weakness of the CO2–cation interaction, the CO2–anion associate is distorted by cations, which can be seen in longer associate distances and reduced “binding” energies. While the single solvating anion is shifted away from CO2, many more solvating cations approach it compared to the case of the gas phase. This leads to the conclusion that while the ionic liquid effect stabilizes charged species, introducing neutral species such as CO2 provides an opposite trend, leading to an inverse ionic liquid effect with the facilitation of carbene formation and thus of chemical absorption.

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The Supporting Information contains the analysis of static quantum chemical calculations at various levels of theory on the systems 1PMe and 1PMe+CO2 with a corresponding discussion, XYZ coordinates and total energies of all optimized structures, video on the contribution of anions and cations to the solvation of CO2 in the IL. This information is available free of charge via the Internet at http://pubs.acs.org/.

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