The use of ionic liquids as a reaction medium for chemical reactions has dramatically increased in recent years, due in large part to numerous reported advances in catalysis and organic synthesis. In some extreme cases, ionic liquids have been shown to induce mechanistic changes relative to conventional solvents. Despite the large interest in the solvents, a clear understanding of the intermolecular interactions behind their chemical impact is lacking. Mixed quantum and molecular mechanical (QM/MM) calculations featuring our recently developed ionic liquid force field have been applied to a wide range of representative reactions including: aldol reactions, Diels-Alder, Kemp eliminations, aromatic nucleophilic substitutions, heterocyclic rearrangements, and beta-eliminations. This seminar details changes along multiple reaction pathways and provides a better understanding of how the immediate solvent environment affects the rates, selectivity, and mechanism. Technical computational advances will also discussed, including the development of a new pairwise long-range electrostatic interaction alternative and force field development efforts.

Modeling chemical reactions in ionic liquids using QM/MM calculations

251st National Meeting (2016)

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