Session: Undergraduate Research Posters: Organic Chemistry:

Diaryliodoniums and their salts represent a class of green, metal-free reagents for the arylation of otherwise challenging systems. Prior experimental and computational studies on these compounds focus on their reactions with small anionic nucleophiles. Diaryliodoniums have been successfully used in systems featuring neutral and large anionic nucleophiles, and the underlying mechanisms remain largely unexplored. Our preliminary work centers on investigating the complexation of aromatic nucleophiles to diaryliodoniums and the mechanistic basis of consequent arylations. A density functional theory (DFT) approach utilizing the MN15 functional with the cc-PVTZ basis set for atoms in rows 1-3 and the SDD effective-core potential (ECP) basis set with added d and f polarization for iodine was used for this study. The data obtained suggest the existence of a small but consequential energy difference between systems featuring lone-pair (typical) vs. pi-pi (novel) coordination between the nucleophile and the hypervalent iodine.

Dr. Thomas Montgomery

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