Keteniminium Salt Chemistry

Keteniminium salts are the cationic intermediates having higly electrophlilic, regioselective and and reactive nature. The keteniminium intermediates are highly functional for organic synthesis leading to formation of biologically activated compounds. These  reactive intermediates are used in a broad range of reactions such as 6p/10p electrocyclization, inter/intramolecular [2+2] cycloaddition, Michael addition, Diels Alder and Pictet-Spengler reactions. By means of density functional theory (DFT) the reaction mechanisms are modeled and properties of keteniminium cations are investigated and rationalized. Furthermore, conceptual DFT methods; Anisotropy of the Induced Current Density (ACIDS), Frontier Molecular Orbital (FMO), Nucleus-Independent Chemical Shift (NICS), Natural Bond Orbital (NBO), Fukui and Parr functions analyses are used to elucidate the reactivity differences and preference of mechanism pathways.