A molecular electron density theory study of the participation of tetrazines in aza-Diels-Alder reactions

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dc.contributor.authorDomingo, L.R.
dc.contributor.authorRíos-Gutiérrez, M.
dc.contributor.authorPérez, P.
dc.date.accessioned2021-11-26T16:51:37Z
dc.date.available2021-11-26T16:51:37Z
dc.date.issued2020-04
dc.descriptionIndexación: Scopuses
dc.description.abstractThe reactions of eight tetrazines of increased electrophilic character with nucleophilic tetramethyl ethylene (TME) and with electrophilic tetracyanoethylene (TCE) have been studied using Molecular Electron Density Theory. These reactions are domino processes comprising an aza-Diels-Alder (ADA) reaction followed by an extrusion of molecular nitrogen, yielding a dihydropyridazine. Analysis of the conceptual DFT (CDFT) indices showed an increase of the electrophilicity and a decrease of the nucleophilicity of tetrazines with an increase of the electron-withdrawing character of the substituent. A very good correlation between the global electron density transfer at the transition structures and the activation enthalpies for the ADA reactions involving TME was found. However, tetrazines have no tendency to react with electrophilic ethylenes such as TCE. Bonding Evolution Theory (BET) analysis of the ADA reaction of dinitro tetrazine with TME showed that the activation energy is mainly associated with the continuous depopulation of the C-C and C-N double bonds. This journal is © 2020 The Royal Society of Chemistry.es
dc.description.urihttps://pubs.rsc.org/en/content/articlelanding/2020/RA/D0RA01548B
dc.identifier.citationRSC Advances Volume 10, Issue 26, Pages 15394 - 1540521 April 2020es
dc.identifier.doi10.1039/d0ra01548b
dc.identifier.issn2046-2069
dc.identifier.urihttp://repositorio.unab.cl/xmlui/handle/ria/21094
dc.language.isoenes
dc.publisherRoyal Society of Chemistryes
dc.rights.licenseAtribución 4.0 Internacional (CC BY 4.0)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/deed.es
dc.subjectMolecular Electron Density Theoryes
dc.subjectElectron density.es
dc.subjectTetrazineses
dc.titleA molecular electron density theory study of the participation of tetrazines in aza-Diels-Alder reactionses
dc.typeArtículoes
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