Solvent effect on Hetero-Diels-Alder reaction of isoselenazole with symmetrical acetylenic dienophiles: A MEDT study

Publication date: Available online 7 March 2019Source: Computational and Theoretical ChemistryAuthor(s): Abdelilah BenallouAbstractA theoretical investigation study by the molecular electron density theory (MEDT) of the role of solvent toluene in the Hetero-Diels-Alder (HDA) reaction of isoselenazole with symmetrical acetylenic dienophiles is carried out, and also a comparative study was performed. The high activation energy involved in this reaction implies a not facile reaction. Whereas, ELF shows a missed pseudoradical formation at the N2 nitrogen atom of isoselenazole moiety increases the possibility of not formation of the new bond principally between N2 and C3 atoms. However, the inclusion of solvent toluene according to the PCM model has successfully reduced the barrier activation by 2.7kcal/mol, additionally the solvent toluene has assisted for the formation of pseudodiradical at N2 and C3 atoms in the earlier reaction through improving the charge transfer. Therefore, a new concept of the role of solvent toluene was effectively discovered by the molecular electron density theory analysis.Graphical abstract

Source: Computational and Theoretical Chemistry - March 7, 2019 Category: Chemistry Source Type: research