DFT modeling of reactivity in an ionic liquid: How many ion pairs?

Fabdznne Bessac, Feliu Maseras

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29 Citations (Scopus)


The modeling of reactivity in an ionic liquid is examined with DFT and DFT/MM calculations on the SN2 intramolecular rearrangement of the Z-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole into 4-benzoylamino-2,5-diphenyl-1,2,3-triazole induced by amines. Experimental research has shown that the reaction occurs in 1-butyl-3-methylimidazolium tetrafluoroborate, and in conventional organic solvents such as acetonitrile with comparable rates. The structure for the reactants, transition states and products for the rate-determining step are optimized, and the energy barrier is computed in three different environments: gas phase, water solvent, and ionic liquid. The results are encouraging in describing the energy barrier in the ionic liquid. A simple model is formulated to explain the effect of the solvent in this particular process, and a procedure to study theoretically the reactivity in an ionic liquid is proposed. © 2007 Wiley Periodicals, Inc.
Original languageEnglish
Pages (from-to)892-899
JournalJournal of Computational Chemistry
Issue number6
Publication statusPublished - 30 Apr 2008


  • DFT
  • Ion pairs
  • Ionic liquids
  • S 2 substitution N
  • Solvation effects


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