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

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

Volume: 8 Issue: 2

Author(s): Raquel Castillo and Juan Andres

Affiliation:

Keywords: Diels-Alder, reactivity indexes, nitrilium, immonium, electrophilicity, nucleophilicity, Huckel molecular orbital (HMO) theory, electrofugality and nucleofugality, Berny analytical gradient, isoprene

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.

Cite this article as:

Castillo Raquel and Andres Juan, A DFT Study of the Reactivity Indexes of Ionic [4 + 2+] Diels-Alder Cycloaddition to Nitrilium and Immonium Ions, Letters in Organic Chemistry 2011; 8 (2) . https://dx.doi.org/10.2174/157017811794697449