Revisiting the Stability of endo/exo Diels-Alder Adducts between Cyclopentadiene and 1,4-benzoquinone

dc.creatorTormena, CF
dc.creatorLacerda, V
dc.creatorde Oliveira, KT
dc.date2010
dc.date2014-11-17T05:24:34Z
dc.date2015-11-26T16:50:37Z
dc.date2014-11-17T05:24:34Z
dc.date2015-11-26T16:50:37Z
dc.date.accessioned2018-03-28T23:37:23Z
dc.date.available2018-03-28T23:37:23Z
dc.identifierJournal Of The Brazilian Chemical Society. Soc Brasileira Quimica, v. 21, n. 1, n. 112, n. 118, 2010.
dc.identifier0103-5053
dc.identifierWOS:000275106400016
dc.identifier10.1590/S0103-50532010000100017
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/79813
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/79813
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/79813
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1275772
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionIn this work it is presented a detailed theoretical analysis of the relative stability of endo/exo Diels-Alder adducts formed by the reaction between cyclopentadiene (1) and 1,4-benzoquinone (2). The intrinsic reaction coordinate (IRC) showed the existence of only one transition state for the reaction studied, for both endo 3 and exo 4 adducts. The energies of both adducts were obtained at high level of theory (CBS-Q) confirming that the endo adduct is more stable than exo, which is in the opposite way to the observed in reactions that usually follow Alder's rule. An electronic structure analysis was performed through NBO methodology, indicating that the attractive delocalization interaction predominates over the steric repulsive interaction in the endo adducts. In summary, for the studied cycloaddition reaction the endo adduct is the thermodynamic and kinetic product, which can be also confirmed by experimental data mentioned in this work.
dc.description21
dc.description1
dc.description112
dc.description118
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionFAPESP [05/59649-0, 06/03980-2, 07/03589-4, 2008/06619-4]
dc.languageen
dc.publisherSoc Brasileira Quimica
dc.publisherSao Paulo
dc.publisherBrasil
dc.relationJournal Of The Brazilian Chemical Society
dc.relationJ. Braz. Chem. Soc.
dc.rightsaberto
dc.sourceWeb of Science
dc.subjectDiels-Alder reaction
dc.subjectendo/exo stability
dc.subjecttheoretical calculation
dc.subjectNBO analysis
dc.subjectSecondary Orbital Interactions
dc.subjectSteric Course
dc.subjectAddition-reactions
dc.subjectDouble-bonds
dc.subjectTransition Structures
dc.subjectStepwise Mechanisms
dc.subjectServing-synthesis
dc.subjectDiene Synthesis
dc.subjectCycloadditions
dc.subjectDensity
dc.titleRevisiting the Stability of endo/exo Diels-Alder Adducts between Cyclopentadiene and 1,4-benzoquinone
dc.typeArtículos de revistas


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