Distortion Rules: Diene Ring Size Effects in Diels-Alder Reactions with Triazolinediones

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dc.contributor.affiliationHernández-Mancera, J.P., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30–65, Medellín, 050026, Colombia
dc.contributor.affiliationRojas-Valencia, N., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30–65, Medellín, 050026, Colombia
dc.contributor.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30–65, Medellín, 050026, Colombia
dc.contributor.authorHernández-Mancera J.P
dc.contributor.authorRojas-Valencia N
dc.contributor.authorNúñez-Zarur F.
dc.date.accessioned2024-07-31T21:06:56Z
dc.date.available2024-07-31T21:06:56Z
dc.date.issued2024
dc.descriptionTriazolinediones (TADs) are highly reactive electrophiles used in several processes within the field of organic chemistry, especially in Diels-Alder cycloadditions. The reactions of TADs with cyclic dienes have been observed to depend on the diene structure and size. To investigate the role of diene structure in the reactivity of TADs, computational chemistry based on DFT and Activation Strain Model were employed to quantitatively assess the impact of distortion and interaction energies on the observed reactivity. Calculations suggest that the reactions are endo selective based on lower energy barriers compared to the exo pathway. Additionally, the trends in reactivity agree with experimental observations: cyclopentadiene is the more reactive diene, followed by cyclohexadiene and cycloheptadiene. The ASM analysis reveals that this trend is a consequence of the degree of distortion the reactants along the reaction coordinate. These distortion energies also allowed to explain why the endo selective route is preferred over the exo one. © 2024 Wiley-VCH GmbH.
dc.identifier.doi10.1002/slct.202304683
dc.identifier.instnameinstname:Universidad de Medellínspa
dc.identifier.issn23656549
dc.identifier.reponamereponame:Repositorio Institucional Universidad de Medellínspa
dc.identifier.repourlrepourl:https://repository.udem.edu.co/
dc.identifier.urihttp://hdl.handle.net/11407/8416
dc.language.isoeng
dc.publisherJohn Wiley and Sons Incspa
dc.publisher.facultyFacultad de Ciencias Básicasspa
dc.relation.citationissue1
dc.relation.citationvolume9
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85181458312&doi=10.1002%2fslct.202304683&partnerID=40&md5=f7a58d51f9c83be0f5934a4b2845a48a
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dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.sourceChemistrySelect
dc.sourceChemistrySelect
dc.sourceScopus
dc.subjectActivation strain modeleng
dc.subjectComputational chemistryeng
dc.subjectCyclic dieneeng
dc.subjectDensity functional calculationseng
dc.subjectDiels-Aldereng
dc.subjectTriazolinedioneeng
dc.titleDistortion Rules: Diene Ring Size Effects in Diels-Alder Reactions with Triazolinedioneseng
dc.typearticle
dc.type.localArtículospa
dc.type.versioninfo:eu-repo/semantics/publishedVersion

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