Computational investigation of cyclic substituted iodine(III) halogen bond donors

Several novel substituted iodine(III)-based halogen bond donors have been computationally investigated using density functional theory (DFT). Their properties of interest related to their Lewis acidity and stability were evaluated. These results constitute a theorical background for the rational design of new active iodine(III)-based organocatalysts. Notably, cyclic diaryliodonium salts with a central six-membered ring (iodininium salts) have been identified as a promising new class of halogen bond donors, although highly Lewis acidic variants have not been synthetized yet.