Unveiling the lewis acid catalyzed diels-alder reactions through the molecular electron density theory

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dc.contributor.authorDomingo, L.R.
dc.contributor.authorRíos-Gutiérrez, M.
dc.contributor.authorPérez, P.
dc.date.accessioned2021-11-22T19:39:44Z
dc.date.available2021-11-22T19:39:44Z
dc.date.issued2020-05
dc.descriptionIndexación: Scopuses
dc.description.abstractThe effects of metal-based Lewis acid (LA) catalysts on the reaction rate and regioselectivity in polar Diels-Alder (P-DA) reactions has been analyzed within the molecular electron density theory (MEDT). A clear linear correlation between the reduction of the activation energies and the increase of the polar character of the reactions measured by analysis of the global electron density transfer at the corresponding transition state structures (TS) is found, a behavior easily predictable by analysis of the electrophilicity ω and nucleophilicity N indices of the reagents. The presence of a strong electron-releasing group in the diene changes the mechanism of these P-DA reactions from a two-stage one-step to a two-step one via formation of a zwitterionic intermediate. However, this change in the reaction mechanism does not have any chemical relevance. This MEDT study makes it possible to establish that the more favorable nucleophilic/electrophilic interactions taking place at the TSs of LA catalyzed P-DA reactions are responsible for the high acceleration and complete regioselectivity experimentally observed. © 2020 by the authors. Licensee MDPI, Basel, Switzerland.es
dc.description.urihttps://www.mdpi.com/1420-3049/25/11/2535
dc.identifier.citationMolecules Volume 25, Issue 11June 2020 Article number 2535es
dc.identifier.doi10.3390/molecules25112535
dc.identifier.issn1420-3049
dc.identifier.urihttp://repositorio.unab.cl/xmlui/handle/ria/21010
dc.language.isoenes
dc.publisherMultidisciplinary Digital Publishing Institute (MDPI)es
dc.rights.licenseAtribución 4.0 Internacional (CC BY 4.0)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/deed.es
dc.subjectRelation mechanism.es
dc.subjectMolecular electron density theory.es
dc.subjectLewis acid.es
dc.subjectDiels-Alder.es
dc.subjectCatalysis.es
dc.titleUnveiling the lewis acid catalyzed diels-alder reactions through the molecular electron density theoryes
dc.typeArtículoes
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