Structural Consequences of Halogen Bonding in Dialkylimidazolium: A New Design Strategy for Ionic Liquids Illustrated with the I2 Cocrystal and Acetonitrile Solvate of 1,3-Dimethylimidazolium Iodide

Kelley, Steven P.; Pei, Hanwen; Smetana, Volodymyr; Mudring, Anja-Verena; Rogers, Robin D.

doi:10.1021/acs.cgd.9b01454

Title: Structural Consequences of Halogen Bonding in Dialkylimidazolium: A New Design Strategy for Ionic Liquids Illustrated with the I₂ Cocrystal and Acetonitrile Solvate of 1,3-Dimethylimidazolium Iodide

Journal Article · 04 December 2019 · Crystal Growth and Design

DOI: https://doi.org/10.1021/acs.cgd.9b01454 · OSTI ID:1657339

^[1]; Pei, Hanwen ^[2];

^[2];

^[3]

Univ. of Alabama, Tuscaloosa, AL (United States); The University of Alabama
Stockholm Univ. (Sweden)
Univ. of Alabama, Tuscaloosa, AL (United States); Stockholm Univ. (Sweden)

The reaction of 1,3-dimethylimidazolium-2-carboxylate with elemental iodine in acetonitrile rapidly affords crystalline iodide salts of the 1,3-dimethyl-2-iodoimidazolium cation ([C₁mim-2-I]⁺), [C₁mim-2-I]I·0.5I₂, and [C₁mim-2-I]I·0.5CH₃CN, depending on the temperature. Analysis of the two structures shows the significant role of halogen bonding interactions between the cation and anion in the [C₁mim-2-I]I salts, which reduces the ionicity of the compounds. This observation is backed by theoretical calculations revealing the importance of halogen bonding as a design strategy for ionic liquids (ILs), which, so far, has been underestimated. Additionally, the halogen bonding is also analyzed in terms of this new design concept for ILs.

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Research Organization:: Univ. of Alabama, Tuscaloosa, AL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Royal Swedish Academy of Science; Swedish Research Council (VR)

Grant/Contract Number:: SC0019220

OSTI ID:: 1657339

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 1 Vol. 20; ISSN 1528-7483

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Anions
Cations
Crystal structure
Halogen bonding
Salts

CCDC 1961533: Experimental Crystal Structure Determination P., Kelley, Steven; Hanwen, Pei,; Volodymyr, Smetana, https://doi.org/10.5517/ccdc.csd.cc23v48d The current record is supplemented by this dataset	dataset	January 2020
CCDC 1961534: Experimental Crystal Structure Determination P., Kelley, Steven; Hanwen, Pei,; Volodymyr, Smetana, https://doi.org/10.5517/ccdc.csd.cc23v49f The current record is supplemented by this dataset	dataset	January 2020

Title: Structural Consequences of Halogen Bonding in Dialkylimidazolium: A New Design Strategy for Ionic Liquids Illustrated with the I2 Cocrystal and Acetonitrile Solvate of 1,3-Dimethylimidazolium Iodide

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Title: Structural Consequences of Halogen Bonding in Dialkylimidazolium: A New Design Strategy for Ionic Liquids Illustrated with the I₂ Cocrystal and Acetonitrile Solvate of 1,3-Dimethylimidazolium Iodide