A DFT Study of the Reactivity Indexes of Ionic [4 + 2+] Diels-Alder Cycloaddition to Nitrilium and Immonium Ions

Abstract

The global electrophilicity index, defined within the conceptual density functional theory (DFT), was used to classify the dienes and dienophiles currently used in Diels-Alder reactions on a unique scale of electrophilicity. The index, obtained within the Kohn-Sham scheme, is based on the HOMO and LUMO energies. A systematic study of the global reactivity indexes of the reagents involved in formal [4 + 2 + ] Diels-Alder cycloaddition reactions of nitrilium and immonium ions with isoprene is presented. © 2011 Bentham Science Publishers Ltd.