Dimerization of ion radicals in ionic liquids. An example of favourable “Coulombic” solvation

Literature Information

Publication Date 2010-06-02
DOI 10.1039/B920552G
Impact Factor 3.676
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Abstract

The irreversible dimerization of the acetophenone radical anion, chosen as an example of a carbon–carbon coupling reaction between two charged species, was investigated in a series of 1,3-dialkylimidazolium and 1,2,3-trialkylimidazolium ionic liquids. Indeed, such ion dimerizations which display slow kinetics despite small activation energies, are controlled by a subtle competition between bond formation, Coulombic repulsion and solvation. The effects of viscosity, “polarity” and ionic solvation on the reactivity of the radical anions were examined. The dimerization rate constants were demonstrated to be only weakly affected by the high viscosity of the medium or its apparent polarity. When the acetophenone radical anion is “solvated” in imidazolium-based ionic liquids, a strong interaction between the negatively-charged intermediates and the imidazolium cation occurs. The ensuing charge stabilization allows a fast dimerization step in all the ionic liquids used. The kinetic effect is even enhanced in the 1,3-dialkylimidazolium salts as compared to the 1,2,3-trialkylimidazolium ones because the interaction between the radical anions and the 1,3-dialkylimidazolium cations are stronger, probably due to the formation of H-bond. The reactivity of the ion radical is demonstrated not only to be mainly dominated by electrostatic interactions, but also that the nature of the ionic liquid cations with respect to that of the ion radical is a major factor that affects the reaction kinetics.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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