Elucidating the N−N and C−N Bond-breaking Mechanism in the Photoinduced Formation of Nitrile Imine

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dc.contributor.authorGuerra, Cristian
dc.contributor.authorAyarde-Henríquez, Leandro
dc.contributor.authorRodríguez-Núñez, Yeray A.
dc.contributor.authorEnsuncho, Adolfo
dc.contributor.authorChamorro, Eduardo
dc.date.accessioned2024-10-29T20:36:52Z
dc.date.available2024-10-29T20:36:52Z
dc.date.issued2023-06
dc.descriptionIndexación: Scopus
dc.description.abstractIn this study, we revealed the significance of chemical bonding for the photochemically induced mechanism of 2-phenyl tetrazole derivatives generating nitrile imines. The correlated electron localization function shows that the formation of imine nitrile involves two key bond events: (i) the heterolytic C−N breakage taking place in the T1 state and (ii) the homolytic N−N rupture occurring in the T2 excited state. In particular, a cation-radical specie results from the C−N cleavage, whereas the N−N rupture creates a biradical resonant form of imine nitrile. Additionally, we noticed that the substantial pair delocalization of the C−C-N bonded structure could play a significant role in the conversion of the biradical imine nitrile into both the propargylic and allenic forms via the T1→S0 deactivation. © 2023 The Authors. ChemPhysChem published by Wiley-VCH GmbH.
dc.description.urihttps://chemistry-europe-onlinelibrary-wiley-com.recursosbiblioteca.unab.cl/doi/10.1002/cphc.202200867
dc.identifier.citationChemPhysChem. Volume 24, Issue 11. 1 June 2023. Article number e202200867
dc.identifier.doi10.1002/cphc.202200867
dc.identifier.issn1439-4235
dc.identifier.urihttps://repositorio.unab.cl/handle/ria/61610
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc
dc.rights.licenseCC BY-NC-ND 4.0 Attribution-NonCommercial-NoDerivatives 4.0 International Deed
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectChemical Bonding
dc.subjectDensity Functional Theory
dc.subjectHeterolytic Scissions
dc.subjectHomolytic Scissions
dc.subjectNitrile Imine
dc.titleElucidating the N−N and C−N Bond-breaking Mechanism in the Photoinduced Formation of Nitrile Imine
dc.typeArtículo
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