New Insights into the Stability of Anhydrous 2H-Imidazolium Fluoride and its High Dissolution Capability toward a Strongly Hydrogen-Bonded Compound

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Huisheng Huang
  • Jie Zhong
  • Xiaoping Tan
  • Xiaogang Guo
  • Binfang Yuan
  • Yinhe Lin
  • Joseph S. Francisco

Detail(s)

Original languageEnglish
Pages (from-to)10314-10318
Journal / PublicationJournal of the American Chemical Society
Volume142
Issue number23
Online published20 May 2020
Publication statusPublished - 10 Jun 2020
Externally publishedYes

Abstract

Fluorides have been widely applied in pharmaceutical, medicinal, and materials science as well as in fine chemical manufacturing. The performance of fluorides, however, can be markedly affected by the water content. One previous study (Maiti, A.; et al. Phys. Chem. Chem. Phys. 2008, 10, 5050) suggested that anhydrous 1,3-dimethylimidazolium fluoride ([DMIm]F) was unstable since the fluoride undergoes a self-decomposition reaction. Herein we first show quantum-chemical calculation evidence that although gas-phase [DMIm]F is unstable, the bulk phase of anhydrous [DMIm]F is quite stable. We then demonstrate the successful synthesis of the anhydrous [DMIm]F compound via the reaction between 1,3-dimethylimidazolium iodide and silver fluoride. Importantly, we find that anhydrous [DMIm]F possesses a high dissolution capability toward 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), although it is known that TATB is hardly dissolved in many common organic solvents. Our Born-Oppenheimer molecular dynamics (BOMD) simulations further show that the high dissolving ability of anhydrous [DMIm]F toward TATB can be attributed to the chemical reaction between the F- anion and the TATB molecules, which disrupts the strong hydrogen-bonding interaction among the TATB molecules. Alternatively, water molecules in hydrous [DMIm]F tend to form a hydration layer around the F- anion, thereby preventing F- from reacting with the TATB molecule. This result explains why TATB is barely dissolved in hydrous [DMIm]F.

Citation Format(s)

New Insights into the Stability of Anhydrous 2H-Imidazolium Fluoride and its High Dissolution Capability toward a Strongly Hydrogen-Bonded Compound. / Huang, Huisheng; Zhong, Jie; Tan, Xiaoping; Guo, Xiaogang; Yuan, Binfang; Lin, Yinhe; Francisco, Joseph S.; Zeng, Xiao Cheng.

In: Journal of the American Chemical Society, Vol. 142, No. 23, 10.06.2020, p. 10314-10318.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review