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The origin of the high reactivity of triazolinediones (TADs) in Diels-Alder reactions from a theoretical perspective

dc.creatorRojas-Valencia N.
dc.creatorNúñez-Zarur F.
dc.date2020
dc.date.accessioned2021-02-05T14:58:55Z
dc.date.available2021-02-05T14:58:55Z
dc.identifier.issn404020
dc.identifier.urihttp://hdl.handle.net/11407/6034
dc.descriptionWe investigate on the origin of the high reactivity of triazolinediones compared to maleimides in Diels-Alder reactions by using a combination of Molecular Orbital Theory and the Activation Strain Model of reactivity. Calculations at M06-2X/6–311++G(d,p)//M06-2X/6-31+G(d) level show that the energy barrier of the cycloaddition between anthracene and triazolinedione is much lower than that for maleimides. The analysis of frontier molecular orbitals (FMO) reveals that for the TAD system there is a much efficient charge transfer as consequence of a more delocalized HOMO over the dienophile fragment at the transition state structure. The Activation Strain Model revealed that the higher reactivity of TAD in the cycloaddition is related to the lower distortion of both fragments to attain the geometry of the transition state. © 2020 Elsevier Ltd
dc.language.isoeng
dc.publisherElsevier Ltd
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85089252149&doi=10.1016%2fj.tet.2020.131459&partnerID=40&md5=64af72f89eb3f1d9aa5034b7155d0d59
dc.sourceTetrahedron
dc.subjectActivation strain modelspa
dc.subjectCharge transferspa
dc.subjectDiels Alderspa
dc.subjectMaleimidesspa
dc.subjectStrain energiesspa
dc.subjectTriazolinedionesspa
dc.titleThe origin of the high reactivity of triazolinediones (TADs) in Diels-Alder reactions from a theoretical perspective
dc.typeArticleeng
dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.identifier.doi10.1016/j.tet.2020.131459
dc.publisher.facultyFacultad de Ciencias Básicasspa
dc.affiliationRojas-Valencia, N., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 Nº 30-65, Medellín, 050026, Colombia
dc.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 Nº 30-65, Medellín, 050026, Colombia
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