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John P Stoppelman1, Jesse G McDaniel1

  • 1School of Chemistry and Biochemistry, Georgia Institute of Technology Atlanta, Georgia 30332-0400, United States.

The Journal of Physical Chemistry. B
|June 6, 2023
PubMed
Summary

N-heterocyclic carbenes (NHCs) are present at ppm levels in 1-ethyl-3-methylimidazolium acetate ionic liquids. Their concentration is significantly enhanced at the liquid/vapor interface due to solvation effects.

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Area of Science:

  • Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • N-heterocyclic carbenes (NHCs) are potent catalysts, but their native presence in imidazolium-based ionic liquids (ILs) like [EMIM+][OAc-] at room temperature is debated.
  • Experimental characterization of transient NHC species is challenging.
  • Ion solvation significantly influences the carbene formation reaction free energy, necessitating computational investigation.

Purpose of the Study:

  • To computationally investigate the formation of NHCs from imidazolium-based ionic liquids.
  • To develop and apply physics-based, neural network reactive force fields for free energy calculations.
  • To understand the influence of bulk and interfacial environments on NHC formation.

Main Methods:

  • Development of physics-based, neural network reactive force fields.
  • Simulation of NHC formation via deprotonation of [EMIM+] by [OAc-].
  • Umbrella sampling to compute reaction free energy profiles in bulk and at the liquid/vapor interface.

Main Results:

  • The bulk ionic liquid environment destabilizes NHC formation compared to the gas phase due to ion solvation energies.
  • Acetic acid shows a preference for proton sharing with acetate in solution and at the interface.
  • Predicted NHC content in bulk [EMIM+][OAc-] is in the parts-per-million (ppm) range.

Conclusions:

  • NHC concentration is orders of magnitude higher at the liquid/vapor interface compared to the bulk.
  • Interfacial enhancement is attributed to poorer solvation of ionic reactants and solvophobic stabilization of neutral NHCs.
  • This study provides quantitative insights into NHC presence in ionic liquids, crucial for catalytic applications.

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