Mechanistic aspects of the synthesis of seven-membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes Molecular Electron Density Theory computational study

Mechanistic aspects of the synthesis of seven-membered internal nitronates via stepwise [4 + 3] cycloaddition involving conjugated nitroalkenes : Molecular Electron Density Theory computational study

© 2022 Wiley Periodicals LLC.

Détails bibliographiques
Publié dans:Journal of computational chemistry. - 1984. - 43(2022), 18 vom: 05. Juli, Seite 1221-1228
Auteur principal: Kącka-Zych, Agnieszka (Auteur)
Autres auteurs: Jasiński, Radomir
Format: Article en ligne
Langue:English
Publié: 2022
Accès à la collection:Journal of computational chemistry
Sujets:Journal Article [4 + 3] cycloaddition reaction molecular electron density theory nitroalkenes nitronates
Description
Résumé:© 2022 Wiley Periodicals LLC.
The density functional theory computational study indicates the possibility of the synthesis of seven-membered internal nitronates via cycloaddition reactions involving Z-C-aryl-N-methylnitrones and E-2-aryl-1-cyano-1-nitroethenes. The detailed exploration of the reaction paths indicates a polar, stepwise reaction mechanism through the zwitterionic intermediate. Using bonding evolution theory (BET), we have deciphered the molecular mechanism of the [4 + 3] cycloaddition reaction between E-2-phenyl-1-cyano-1-nitroethene and Z-C-phenyl-N-methylnitrone. The BET study has revealed that the formation of two CO single bonds takes place in the same way, through the depopulation of NC and CC bonding regions and monosynaptic basins, respectively. The first O1C7 single bond was formed in the sixth phase, while the second C3O4 bond was formed in the last ninth phase
Description:Date Revised 27.05.2022
published: Print-Electronic
Citation Status PubMed-not-MEDLINE
ISSN:1096-987X
DOI:10.1002/jcc.26885