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    • WISSENSCHAFTLICHE ARBEITEN
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    Por favor, use este identificador para citar o enlazar este ítem:https://uvadoc.uva.es/handle/10324/48998

    Título
    How aromatic fluorination exchanges the interaction role of pyridine with carbonyl compounds: The formaldehyde adduct
    Autor
    López Alonso, Juan CarlosAutoridad UVA Orcid
    Macario Farto, AlbertoAutoridad UVA Orcid
    Maris, Assimo
    Alkorta, Ibon
    Blanco Rodríguez, SusanaAutoridad UVA Orcid
    Año del Documento
    2021
    Editorial
    Wiley
    Descripción
    Producción Científica
    Documento Fuente
    Chemistry – A European Journal, 2021, vol. 27, n. 55, p.13870 –13878
    Zusammenfassung
    The rotational spectrum of the weakly bound complex pentafluoropyridineꞏꞏꞏformaldehyde has been investigated using Fourier transform microwave spectroscopy. From the analysis of the rotational parameters of the parent species and of the 13C and 15N isotopologues, the structural arrangement of the adduct has been unambiguously established. The full ring fluorination of pyridine has a dramatic effect on its binding properties: It alters the electron density distribution at the π-cloud of pyridine creating a π-hole and changing its electron donor-acceptor capabilities. In the complex, formaldehyde lies above the aromatic ring with one of the oxygen lone pairs, as conventionally envisaged, pointing toward its centre. This lone pairꞏꞏꞏπ-hole interaction, reinforced by a weak C-HꞏꞏꞏN interaction, indicates an exchange of the electron-acceptor roles of both molecules when compared to the pyridineꞏꞏꞏformaldehyde adduct. Tunnelling doublets due to the internal rotation of formaldehyde have also been observed and analysed leading to a discussion on the competition between lone pairꞏꞏꞏπ-hole and π ꞏꞏꞏπ staking interactions.
    Materias Unesco
    23 Química
    Palabras Clave
    Aromatic fluorination
    Pyridine
    Carbonyl compounds
    Pentafluoropyridine
    Formaldehyde
    ISSN
    0947-6539
    Revisión por pares
    SI
    DOI
    10.1002/chem.202102163
    Patrocinador
    Ministerio de Economía y Competitividad (grant CTQ2016-75253-P)
    Ministerio de Ciencia, Innovación y Universidades de España (project PGC2018-094644-B-C22)
    Comunidad Autónoma de Madrid (grant P2018 / EMT-4329 AIRTEC-CM)
    Version del Editor
    https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202102163
    Propietario de los Derechos
    © 2021 The Authors
    Idioma
    eng
    URI
    https://uvadoc.uva.es/handle/10324/48998
    Tipo de versión
    info:eu-repo/semantics/publishedVersion
    Derechos
    openAccess
    Aparece en las colecciones
    • DEP63 - Artículos de revista [324]
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    Dateien zu dieser Ressource
    Nombre:
    How-aromatic-fluorination-exchanges.pdf
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