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Diels-Alder reaction mechanisms of substituted chiral anthracene: A theoretical study based on the reaction force and reaction electronic flux

dc.creatorHernández Mancera J.P.
dc.creatorNúñez-Zarur F.
dc.creatorGutiérrez-Oliva S.
dc.creatorToro-Labbé A.
dc.creatorVivas-Reyes R.
dc.date2020
dc.date.accessioned2021-02-05T14:58:06Z
dc.date.available2021-02-05T14:58:06Z
dc.identifier.issn1928651
dc.identifier.urihttp://hdl.handle.net/11407/5939
dc.descriptionQuantum chemical calculations were used to study the mechanism of Diels-Alder reactions involving chiral anthracenes as dienes and a series of dienophiles. The reaction force analysis was employed to obtain a detailed scrutiny of the reaction mechanisms, it has been found that thermodynamics and kinetics of the reactions are quite consistent: the lower the activation energy, the lower the reaction energy, thus following the Bell-Evans-Polanyi principle. It has been found that activation energies are mostly due to structural rearrangements that in most cases represented more than 70% of the activation energy. Electronic activity mostly due to changes in σ and π bonding were revealed by the reaction electronic flux (REF), this property helps identify whether changes on σ or π bonding drive the reaction. Additionally, new global indexes describing the behavior of the electronic activity were introduced and then used to classify the reactions in terms of the spontaneity of their electronic activity. Local natural bond order electronic population analysis was used to check consistency with global REF through the characterization of specific changes in the electronic density that might be responsible for the activity already detected by the REF. Results show that reactions involving acetoxy lactones are driven by spontaneous electronic activity coming from bond forming/strengthening processes; in the case of maleic anhydrides and maleimides it appears that both spontaneous and non-spontaneous electronic activity are quite active in driving the reactions. © 2020 Wiley Periodicals LLC
dc.language.isoeng
dc.publisherJohn Wiley and Sons Inc.
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85087162376&doi=10.1002%2fjcc.26360&partnerID=40&md5=f7de9efcd429c79b448188de5f2fdaf7
dc.sourceJournal of Computational Chemistry
dc.subjectchiral anthracenespa
dc.subjectdiels Alders reaction mechanismsspa
dc.subjectreaction electronic flux (REF)spa
dc.subjectreaction force analysisspa
dc.titleDiels-Alder reaction mechanisms of substituted chiral anthracene: A theoretical study based on the reaction force and reaction electronic flux
dc.typeArticleeng
dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.identifier.doi10.1002/jcc.26360
dc.subject.keywordActivation analysiseng
dc.subject.keywordActivation energyeng
dc.subject.keywordAnthraceneeng
dc.subject.keywordChemical bondseng
dc.subject.keywordQuantum chemistryeng
dc.subject.keywordStereochemistryeng
dc.subject.keywordThermodynamicseng
dc.subject.keywordDiels-Alder reactioneng
dc.subject.keywordNatural bond orderseng
dc.subject.keywordPopulation analysiseng
dc.subject.keywordQuantum chemical calculationseng
dc.subject.keywordReaction electronic flux (REF)eng
dc.subject.keywordReaction electronic fluxeseng
dc.subject.keywordStructural rearrangementeng
dc.subject.keywordThermodynamics and kineticseng
dc.subject.keywordReaction kineticseng
dc.publisher.facultyFacultad de Ciencias Básicasspa
dc.affiliationHernández Mancera, J.P., Grupo de Química Cuántica y Teórica, Facultad de Ciencias Exactas y Naturales, Universidad de Cartagena, Cartagena, Colombia
dc.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Medellín, Colombia
dc.affiliationGutiérrez-Oliva, S., Laboratorio de Química Teórica Computacional (QTC), Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Santiago, Chile
dc.affiliationToro-Labbé, A., Laboratorio de Química Teórica Computacional (QTC), Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Santiago, Chile
dc.affiliationVivas-Reyes, R., Grupo de Química Cuántica y Teórica, Facultad de Ciencias Exactas y Naturales, Universidad de Cartagena, Cartagena, Colombia, Grupo CipTec, Fundación Universitaria Tecnológico de Comfenalco, Facultad de Ingenierías, Programa de Ingeniería Industrial, Cartagena de Indias, Bolivar, Colombia
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