ArticleMolecules (Basel, Switzerland)2025
Photochemical Rearrangements of Pyridine N-Oxides: Pathways to Oxaziridine Derivatives.
Cristian J Guerra, Yeray A Rodríguez-Núñez, Efraín Polo-Cuadrado, Mitchell Bacho, Jorge Soto-Delgado, Victor B Fuentes-Guerrero, Eduardo I Torres-Olguín, Cristopher A Fica-Cornejo, Daniela Rodríguez-García, Manuel E Taborda-Martínez and 2 more
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In one paragraphArticle in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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5 · Who and what moneyAuthors and funding
12 authors.
Cristian J GuerraLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.ORCID 0000-0002-9664-2504 Yeray A Rodríguez-NúñezLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.ORCID 0000-0003-4935-876X Efraín Polo-CuadradoLaboratorio de Diseño y Síntesis de Compuestos Bioactivos, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Concepción 4070386, Chile.ORCID 0000-0003-2280-9321 Mitchell BachoDepartamento de Ciencias Biológicas y Químicas, Facultad de Medicina y Ciencia, Universidad San Sebastián, Campus los Leones, Lota 2465, Providencia, Santiago 7510602, Chile.
Jorge Soto-DelgadoDepartamento de Ciencias Químicas, Facultad de Ciencias Exactas Bello, Universidad Andrés Bello, Quillota 980, Viña del Mar 2531015, Chile.ORCID 0000-0002-2983-1727 Victor B Fuentes-GuerreroLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.
Eduardo I Torres-OlguínLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.ORCID 0009-0006-7023-5181 Cristopher A Fica-CornejoLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.ORCID 0009-0001-1250-0841 Daniela Rodríguez-GarcíaLaboratorio de Síntesis y Reactividad de Compuestos Orgánicos, Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, República 275, Santiago 8370146, Chile.ORCID 0009-0004-2829-7480 Manuel E Taborda-MartínezFacultad de Ciencias de la Educación, Universidad del Magdalena, Carrera 32 No. 22-08, Santa Marta 470004, Colombia.
Adolfo E EnsunchoGrupo de Química Computacional, Facultad de Ciencias Básicas, Universidad de Córdoba, Carrera 6 No. 77-305, Montería-Córdoba 230001, Colombia.
Funding
No grant is acknowledged in the PubMed record.
6 · The paper itselfAbstract
The photochemical behavior of substituted pyridine N-Oxides is characterized by complex rearrangements culminating in the formation of valuable photoproducts. The CAS(10,8)/cc-pVDZ approach with NEVPT2 corrections is applied to investigate geometric distortions associated with the S1 excited state, conical intersections, and the ultimate transformation of pyridine N-Oxides into oxaziridine-like derivative formations. Our results reveal that the deactivation of the S1 excited state is driven by an out-of-plane rotation of the N-O oxygen atom, resulting in the formation of a lone pair over the nitrogen atom. Along this excited-state reaction pathway, the N-O bond undergoes significant weakening, while a C=C double bond emerges mainly in the excited state. The deactivation at the minimum-energy conical intersection leading to the ground state reveals the formation of an oxaziridine-like intermediate, which subsequently converts into a 1,2-oxazepine derivative.
Indexed as
ab initio calculationscharge redistributionphotochemical rearrangementsthermochemistry
Identifiers
PMID41471800
PMCPMC12736228
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