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

Huisheng Huang, Jie Zhong, Xiaoping Tan, Xiaogang Guo, Binfang Yuan, Yinhe Lin, Joseph S. Francisco, Xiao Cheng Zeng

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)10314-10318
Number of pages5
JournalJournal of the American Chemical Society
Volume142
Issue number23
DOIs
StatePublished - Jun 10 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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