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Diels-Alder Reactivity of a Chiral Anthracene Template with Symmetrical and Unsymmetrical Dienophiles: A DFT Study

dc.creatorHernández-Mancera J.P.
dc.creatorNúñez-Zarur F.
dc.creatorVivas-Reyes R.
dc.date2020
dc.date.accessioned2021-02-05T14:58:07Z
dc.date.available2021-02-05T14:58:07Z
dc.identifier.issn21911363
dc.identifier.urihttp://hdl.handle.net/11407/5940
dc.descriptionIn this work, we used Density Functional Theory calculations to assess the factors that control the reactivity of a chiral anthracene template with three sets of dienophiles including maleic anhydrides, maleimides and acetoxy lactones in the context of Diels-Alder cycloadditions. The results obtained here (at the M06-2X/6-311++G(d,p) level of theory) suggest that the activation energies for maleic anhydrides and acetoxy lactones are dependent on the nature of the substituent in the dienophile. Among all studied substituents, only −CN reduces the energy barrier of the cycloaddition. For maleimides, the activation energies are independent of the heteroatom of the dienophile and the R group attached to it. The analysis of frontier molecular orbitals, charge transfer and the activation strain model (at the M06-2X/TZVP level based on M06-2X/6-311++G(d,p) geometries) suggest that the activation energies in maleic anhydrides are mainly controlled by the amount of charge transfer from the diene to the dienophile during cycloaddition. For maleimides, there is a dual control of interaction and strain energies on the activation energies, whereas for the acetoxy lactones the activation energies seem to be controlled by the degree of template distortion at the transition state. Finally, calculations show that considering a catalyst on the studied cycloadditions changes the reaction mechanism from concerted to stepwise and proceed with much lower activation energies. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
dc.language.isoeng
dc.publisherWiley-VCH Verlag
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85088831022&doi=10.1002%2fopen.202000137&partnerID=40&md5=fdd21c1abeaf2fdd7f7370753745820c
dc.sourceChemistryOpen
dc.subjectactivation strain modelspa
dc.subjectcharge transferspa
dc.subjectchiral anthracenesspa
dc.subjectDFT calculationsspa
dc.subjectDiels-Alder reactionsspa
dc.titleDiels-Alder Reactivity of a Chiral Anthracene Template with Symmetrical and Unsymmetrical Dienophiles: A DFT Study
dc.typeArticleeng
dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.identifier.doi10.1002/open.202000137
dc.relation.citationvolume9
dc.relation.citationissue7
dc.relation.citationstartpage748
dc.relation.citationendpage761
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, Campus San Pablo, Cartagena, 130015, Colombia
dc.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30–65, Medellín, 050026, Colombia
dc.affiliationVivas-Reyes, R., Grupo de Química Cuántica y Teórica, Facultad de Ciencias Exactas y Naturales, Universidad de Cartagena, Campus San Pablo, Cartagena, 130015, Colombia, Grupo CipTec, Fundación Universitaria, Tecnológico de Comfenalco, Facultad de Ingenierías Cartagena de Indias, Bolívar, 130001, Colombia
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