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.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.relation.projectID |
info:eu-repo/grantAgreement/MICINN//CTQ2009-11027/ES/Estudios de reactividad en química orgánica/ |
es_ES |
dc.relation.projectID |
info:eu-repo/grantAgreement/FONDECYT//1100278/ |
|
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. https://doi.org/10.1016/j.tet.2012.10.056 |
es_ES |
dc.description.accrualMethod |
S |
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 |
Fondo Nacional de Desarrollo Científico y Tecnológico, Chile |
|
dc.contributor.funder |
Ministerio de Ciencia e Innovación |
es_ES |