dc.contributor.author | López Francés, Adrián | |
dc.contributor.author | Del Corte Solaguren-Beascoa, Xabier | |
dc.contributor.author | Serna Burgos, Zuriñe | |
dc.contributor.author | De los Santos Ruiz, Jesús Manuel | |
dc.contributor.author | De Cózar Ruano, Abel | |
dc.contributor.author | Vicario Hernando, Javier | |
dc.date.accessioned | 2024-01-17T14:21:45Z | |
dc.date.available | 2024-01-17T14:21:45Z | |
dc.date.issued | 2023-10 | |
dc.identifier.citation | Organic Chemistry Frontiers 24(10) : 6103-6111 (2023) | es_ES |
dc.identifier.issn | 2052-4129 | |
dc.identifier.uri | http://hdl.handle.net/10810/64059 | |
dc.description.abstract | Hermaphroditism of molecules: as in nature some species behave as male or female depending on the environment, herein we report a bispericyclic dimerisation of cyclic 1-azadienes where a molecule can behave as either diene or dienophile, depending on its location at the transition state. In a symmetrical reactive complex, here represented by an arbitrary reference system, a molecule that is positioned on top acts as the diene unit, while the dienophile partner is the one situated at the bottom. In addition, a strong chiral self-recognition phenomenon is observed, where each enantiomer within a racemic mixture of chiral 1-azadienes exclusively recognises itself. In order to shed some light into the understanding of the chiral self-recognition effect, an extensive DFT study of the reaction pathway is provided, concluding that a combination of attractive π-stacking forces and repulsive steric interactions is at the origin of the high stereospecificity of the reaction. | es_ES |
dc.description.sponsorship | Financial support by Ministerio de Ciencia, Innovación y Universidades (MCIU-Madrid) (PID2021-122558OB-I00, UE), and Eusko Jaurlaritza (GV, IT1701-22 and IT-1553-22; UPV-EHU) is gratefully acknowledged. The authors are grateful for technical and human support provided by SGIker (UPV/EHU/ERDF, EU). The authors thank SGI/IZO-SGIker of the UPV/EHU and the DIPC for the generous allocation of analytical and computational resources. A. L.-F. thanks the Basque Country Government for a predoctoral grant. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | RSC | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2021-122558OB-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es/ | * |
dc.title | Chiral self-recognition in a bispericyclic cyclodimerisation reaction of 1-azadienes | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | This article is licensed undar a Creative Commons Attribution 3.0 Unported license. | es_ES |
dc.rights.holder | Atribución 3.0 España | * |
dc.relation.publisherversion | https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo01562a | es_ES |
dc.identifier.doi | 10.1039/d3qo01562a | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |