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The structure of N-(5-aminopyrimidin-2-yl)-N-methyl-2-methoxymethylaniline in solid state (X-ray crystallography) and in solution (NMR) and determination of its protonation site

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dc.contributor.authorReviriego, Felipe
dc.contributor.authorDelgado Martínez, Patricia
dc.contributor.authorTorralba, María del Carmen
dc.contributor.authorClaramunt, Rosa M.
dc.contributor.authorAlkorta, Ibon
dc.contributor.authorElguero, José
dc.contributor.funderAgencia Estatal de Investigación (AEI)
dc.date.accessioned2025-10-09T09:40:09Z
dc.date.available2025-10-09T09:40:09Z
dc.date.issued2025-09-27
dc.descriptionThe registered version of this article, first published in Journal of Molecular Structure 1351 (Part 1) 144176, is available online at the publisher's website: https://doi.org/10.1016/j.molstruc.2025.144176
dc.descriptionLa versión registrada de este artículo, publicado por primera vez en Journal of Molecular Structure 1351 (Part 1) 144176, está disponible en línea en el sitio web del editor: https://doi.org/10.1016/j.molstruc.2025.144176
dc.descriptionThis work was carried out with financial support from the Ministerio de Ciencia, Innovación y Universidades (PID2021–125207NB-C32). Library and scientific-technical services of the Universidad Nacional de Educación a Distancia (UNED) are greatly acknowledged. Thanks are also given to the CTI (CSIC) for their continued computational support
dc.description.abstractThe structure of the title compound was determined both in the solid state by crystallography and in solution by NMR, particularly concerning the conformation around the C2–N8 bond. Hirshfeld surface (HS) analysis of this molecule was performed, using Crystal Explorer 25.09, in order to evaluate the zones of potential intermolecular contacts in the crystal as well as to determine the atoms involved. As crystals of the protonated form could not be obtained due to the rapid decomposition of the pyrimidine ring, multinuclear 1H, 13C, and 15N NMR spectroscopy was employed. This revealed that protonation occurs on the ring nitrogens in a 90/10 ratio. Theoretical calculations of geometries and energies have been carried out at the Becke Three-parameter Lee–Yang–Parr (B3LYP)/6–311++G(d,p) level, and the optimized structures used to calculate chemical shifts via the Gauge-Invariant Atomic Orbital (GIAO) method. These calculations were crucial to draw definitive conclusions.en
dc.description.versionversión publicada
dc.identifier.citationFelipe Reviriego, Patricia Delgado-Martínez, M. Carmen Torralba, Rosa M. Claramunt, Ibon Alkorta, José Elguero The structure of N-(5-aminopyrimidin-2-yl)-N-methyl-2-methoxymethylaniline in solid state (X-ray crystallography) and in solution (NMR) and determination of its protonation site Journal of Molecular Structure 1351 (2026) 144176. https://doi.org/10.1016/j.molstruc.2025.144176
dc.identifier.doihttps://doi.org/10.1016/j.molstruc.2025.144176
dc.identifier.issn0022-2860 | eISSN 1872-8014
dc.identifier.urihttps://hdl.handle.net/20.500.14468/30356
dc.journal.titleJournal of Molecular Structure
dc.journal.volume1351
dc.language.isoen
dc.publisherElsevier
dc.relation.centerFacultad de Ciencias
dc.relation.departmentQuímica Orgánica y Bio-Orgánica
dc.relation.projectidinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021–125207NB-C32/ES/PARES DE LEWIS FRUSTRADOS Y NUEVOS MATERIALES BASADOS EN BORO Y BERILIO: CARACTERIZACION ESPECTROSCOPICA Y MODELIZACION COMPUTACIONAL
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
dc.subject2306 Química orgánica
dc.subject2302 Bioquímica
dc.subject.keywords5-aminopyrimidinesen
dc.subject.keywordsX-ray crystallographyen
dc.subject.keywordsB3LYP/6-311++G(d,p) calculationsen
dc.subject.keywordsProtonation siteen
dc.titleThe structure of N-(5-aminopyrimidin-2-yl)-N-methyl-2-methoxymethylaniline in solid state (X-ray crystallography) and in solution (NMR) and determination of its protonation siteen
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dc.typejournal articleen
dspace.entity.typePublication
relation.isAuthorOfPublicationbd6cfe0a-be8f-48cd-aac5-7c34967578e7
relation.isAuthorOfPublication.latestForDiscoverybd6cfe0a-be8f-48cd-aac5-7c34967578e7
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