Computational study of the supramolecular complexation of azocompounds with cucurbit[7]uril: effects on the production and release of free radicals

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dc.article.number337
dc.catalogadorgjm
dc.contributor.authorForero Girón, Angie
dc.contributor.authorGutiérrez Oliva, Soledad
dc.contributor.authorLópez Alarcón, Camilo Ignacio
dc.contributor.authorHerrera Pisani, Bárbara Andrea
dc.contributor.authorAliaga Miranda, Margarita Elly
dc.date.accessioned2025-01-02T16:36:34Z
dc.date.available2025-01-02T16:36:34Z
dc.date.issued2024
dc.description.abstractContext: An inclusion complex between 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH), a widely employed azocompound, and cucurbit[7]util (CB[7]), has shown an increased yield of radicals derived from the homolytic cleavage of the azo bond. Aimed to get insights about the formation of complexes and their effect on the yield of radicals production, complexes of CB[7] with seven azocompounds were studied by computational methods. Molecular electrostatic surfaces and structural analysis showed that the inclusion of symmetrical azocompounds inside of CB[7] depends mainly on the charge density and position of the functional groups at the main chain of the azoderivative. Analysis of non-covalent interactions and thermodynamic outcomes revealed that positively charged azocompounds with amidinium or imidazolium groups presented strong favorable interactions (multiple hydrogen bonds) with the oxygens of CB[7] portals. Additionally, carbon-centered radicals generated from the complexes (azocompounds@CB[7]) were corroborated using the electron localization function (ELF). Results evidenced that the strength of the interactions and the level of inclusion (partial or complete) between the azocompound and CB[7] determined the final orientation of the radicals (located out- or inside of the CB[7] cavity). Obtained results could be employed to design new supramolecular systems based on the properties of azocomplound@CB[7] complexes for new scientific or industrial applications. Methods: First-principles calculations at B3LYP-D3BJ/6-311g(d,p) level theory in the gas phase and in solvent (PCM, water) were performed in Gaussian 16 software package. The dispersion energy correction was included through the Grimme’s dispersion with Becke-Johnson damping D3(BJ). Thermodynamical data and the minimum character of all structures were obtained from vibrational frequency calculations. NBO, Multiwfn, Chemcraft, and NCIPLOT software were used to perform population analysis, analyze outcomes, visualize data, and display non-covalent interactions respectively.
dc.description.funderFondecyt
dc.description.funderFondecyt
dc.format.extent13 páginas
dc.fuente.origenSCOPUS
dc.identifier.doi10.1007/s00894-024-06132-7
dc.identifier.issn0948-5023
dc.identifier.scopusidSCOPUS_ID:85204288608
dc.identifier.urihttps://doi.org/10.1007/s00894-024-06132-7
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/89455
dc.information.autorucEscuela de Química; Forero Girón, Angie; S/I; 1050653
dc.information.autorucEscuela de Química; Gutiérrez Oliva, Soledad; 0000-0002-3436-1985; 1004064
dc.information.autorucEscuela de Química; López Alarcón, Camilo Ignacio; S/I; 1004308
dc.information.autorucEscuela de Química; Herrera Pisani, Bárbara Andrea; 0000-0003-1911-4473; 4439
dc.information.autorucEscuela de Química; Aliaga Miranda, Margarita Elly; 0000-0002-4143-0301; 13361
dc.language.isoen
dc.nota.accesocontenido parcial
dc.publisherSpringer Science and Business Media Deutschland GmbH
dc.revistaJournal of Molecular Modeling
dc.rightsacceso restringido
dc.subjectAlkyl radicals
dc.subjectAzocompounds
dc.subjectComputational chemistry
dc.subjectCucurbit[7]uril complexes
dc.subjectPeroxyl radicals
dc.subjectSupramolecular radical chemistry
dc.subject.ddc510
dc.subject.deweyMatemática física y químicaes_ES
dc.subject.ods09 Industry, innovation and infrastructure
dc.subject.odspa09 Industria, innovación e infraestructura
dc.titleComputational study of the supramolecular complexation of azocompounds with cucurbit[7]uril: effects on the production and release of free radicals
dc.typeartículo
dc.volumen30
sipa.codpersvinculados1050653
sipa.codpersvinculados1004064
sipa.codpersvinculados1004308
sipa.codpersvinculados4439
sipa.codpersvinculados13361
sipa.trazabilidadSCOPUS;2024-09-29
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