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Understanding the regioselectivity in hetero Diels-Alder reactions. An ELF analysis of the reaction between nitrosoethylene and 1-vinylpyrrolidine.

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Understanding the regioselectivity in hetero Diels-Alder reactions. An ELF analysis of the reaction between nitrosoethylene and 1-vinylpyrrolidine.

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dc.contributor.author Domingo, Luis R. es_ES
dc.contributor.author Pérez, Patricia es_ES
dc.contributor.author Sáez-Cases, José Antonio es_ES
dc.date.accessioned 2017-07-18T11:45:42Z
dc.date.available 2017-07-18T11:45:42Z
dc.date.issued 2013-01-07
dc.identifier.issn 0040-4020
dc.identifier.uri http://hdl.handle.net/10251/85398
dc.description.abstract [EN] The regioselectivity in the hetero Diels-Alder reaction between nitrosoethylene 1 and 1-vinylpyrrolidine 2 has been studied by a comparative ELF bonding analysis along the IRC of the endo/ortho and endo/meta regioisomeric channels at the B3LYP/6-31G*. level. Along the most favorable endo/ortho regioisomeric channel, the C-C sigma bond is first formed by coupling of two pseudoradical centers located at the most electrophilic carbon of 1 and the most nucleophilic center of 2. Formation of these relevant pseudoradical centers, which depend on the total charge transfer process along the polar reaction, and not on the approach mode of each reagent, is well characterized by analysis of the atomic spin density in the radical anion of nitrosoethylene 1 and in the radical cation of vinylpyrrolidine 2. (C) 2012 Elsevier Ltd. All rights reserved. es_ES
dc.description.sponsorship We are grateful to the Spanish Government (project CTQ2009-11027/BQU), and the Fondecyt project No. 1100278. Professor L.R.D. also thanks Fondecyt by support through the Cooperacion Internacional.
dc.language Inglés es_ES
dc.publisher Elsevier es_ES
dc.relation MINECO/CTQ2009-1102/BQU es_ES
dc.relation FONDECYT/1100278
dc.relation.ispartof Tetrahedron es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Electron localization function es_ES
dc.subject Topological analysis es_ES
dc.subject Bond-formation es_ES
dc.subject Quantitative characterization es_ES
dc.subject Cycloaddition reaction es_ES
dc.subject Density es_ES
dc.subject Electrophilicity es_ES
dc.subject Index es_ES
dc.subject 1,3-Dipolar es_ES
dc.subject Parameter es_ES
dc.title Understanding the regioselectivity in hetero Diels-Alder reactions. An ELF analysis of the reaction between nitrosoethylene and 1-vinylpyrrolidine. es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1016/j.tet.2012.10.056
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Domingo, LR.; Pérez, P.; Sáez-Cases, JA. (2013). Understanding the regioselectivity in hetero Diels-Alder reactions. An ELF analysis of the reaction between nitrosoethylene and 1-vinylpyrrolidine. Tetrahedron. 69(1):107-114. doi:10.1016/j.tet.2012.10.056 es_ES
dc.description.accrualMethod Senia es_ES
dc.relation.publisherversion http://doi.org/10.1016/j.tet.2012.10.056 es_ES
dc.description.upvformatpinicio 107 es_ES
dc.description.upvformatpfin 114 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 69 es_ES
dc.description.issue 1 es_ES
dc.relation.senia 241466 es_ES
dc.contributor.funder Ministerio de Economía y Competitividad
dc.contributor.funder Fondo Nacional de Desarrollo Científico y Tecnológico, Chile


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