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

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dc.contributor.authorDomingo, Luis R.
dc.contributor.authorRíos-Gutiérrez, Mar
dc.contributor.authorPérez, Patricia
dc.date.accessioned2024-07-10T19:52:49Z
dc.date.available2024-07-10T19:52:49Z
dc.date.issued2020-06
dc.descriptionIndexación: Scopus.
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.
dc.description.urihttps://www.mdpi.com/1420-3049/25/11/2535
dc.identifier.citationMolecules Volume 25, Issue 11June 2020 Article number 2535
dc.identifier.doi10.3390/molecules25112535
dc.identifier.issn1420-3049
dc.identifier.urihttps://repositorio.unab.cl/handle/ria/58402
dc.language.isoen_US
dc.publisherMDPI AG
dc.rights.licenseATRIBUCIÓN 4.0 INTERNACIONAL
dc.rights.urihttps://www.mdpi.com/1420-3049/25/11/2535
dc.subjectCatalysis
dc.subjectDiels-Alder
dc.subjectLewis acid
dc.subjectMolecular electron density theory
dc.subjectRelation mechanism
dc.titleUnveiling the lewis acid catalyzed diels-alder reactions through the molecular electron density theory
dc.typeArtículo
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