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    Por favor, use este identificador para citar o enlazar este ítem:http://uvadoc.uva.es/handle/10324/45883

    Título
    Intrinsic antioxidant potential of the aminoindole structure: A computational kinetics study of tryptamine
    Autor
    Bentz, Erika N.
    Lobayan, Rosana M.
    Martínez García, María del HenarAutoridad UVA Orcid
    Redondo Cristóbal, María del PilarAutoridad UVA Orcid
    Largo Cabrerizo, AntonioAutoridad UVA Orcid
    Año del Documento
    2018
    Editorial
    ACS Publications
    Descripción
    Producción Científica
    Documento Fuente
    The Journal of Physical Chemistry B, 2018, vol. 122, n. 24. p. 6386–6395
    Zusammenfassung
    A computational kinetics study of the antioxidant activity of tryptamine toward HO• and HOO• radicals in water at 298 K has been carried out. Density functional methods have been employed for the quantum chemical calculations, and the conventional transition state theory was used for rate constant evaluation. Different mechanisms have been considered: radical adduct formation (RAF), single electron transfer (SET), and hydrogen atom transfer (HAT). For the reaction of tryptamine with the hydroxyl radical, nearly all channels are diffusion-controlled, and the overall rate constant is very high, 6.29 × 1010 M–1 s–1. The RAF mechanism has a branching ratio of 55%, followed by the HAT mechanism (31%), whereas the SET mechanism accounts just for 13% of the products. The less hindered carbon atom neighboring to the nitrogen of the indole ring seems to be the preferred site for the RAF mechanism, with a branching ratio of 16%. The overall rate constant for the reaction of tryptamine with the HOO• radical is 3.71 × 104 M–1 s–1, suggesting that it could be a competitive process with other reactions of hydroperoxyl radicals in biological environments. For this reaction only the HAT mechanism seems viable. Furthermore, only two centers may contribute to the HAT mechanism, the nitrogen atom of the indole ring and a carbon atom of the aminoethyl chain, the former accounting for more than 91% of the total products. Our results suggest that tryptamine could have a noticeable scavenging activity toward radicals, and that this activity is mainly related to the nitrogen atom of the indole ring, thus showing the relevance of their behavior in the study of aminoindoles.
    Palabras Clave
    Aminoindole
    Aminoindol
    Tryptamine
    Triptamina
    Transition states
    Estados de transición
    Chemical reactions
    Reacciónes químicas
    ISSN
    1520-5207
    Revisión por pares
    SI
    DOI
    10.1021/acs.jpcb.8b03807
    Patrocinador
    Universidad Nacional del Nordeste (grant F008-2013)
    Ministerio de Economía, Industria y Competitividad (grant AYA2017-87515-P)
    Version del Editor
    https://pubs.acs.org/doi/10.1021/acs.jpcb.8b03807
    Propietario de los Derechos
    © 2018 ACS Publications
    Idioma
    eng
    URI
    http://uvadoc.uva.es/handle/10324/45883
    Tipo de versión
    info:eu-repo/semantics/acceptedVersion
    Derechos
    openAccess
    Aparece en las colecciones
    • DEP63 - Artículos de revista [322]
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    Dateien zu dieser Ressource
    Nombre:
    Intrinsic-antioxidant-potential.pdf
    Tamaño:
    1.113Mb
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