Influence of the CH/B replacement on the reactivity of boranthrene and related compounds

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dc.citation.titleACS Organic & Inorganic Au
dc.citation.volume44-52
dc.citation.volume2
dc.creatorCortés, Iván
dc.creatorCabrera Trujillo, Jorge Juan
dc.creatorFernández, Israel
dc.date.accessioned2024-04-05T13:51:22Z
dc.date.available2024-04-05T13:51:22Z
dc.date.issued2022-02-02
dc.description.abstractThe influence of the replacement of CH groups by boron atoms on the reactivity of planar polycyclic aromatic hydrocarbons has been explored by means of computational tools. To this end, [4 + 2]-cycloaddition reactions involving anthracene and neutral boranthrene with different dienophiles such as ethylene, acetylene, and CO2 have been compared. In addition, the influence of additional fused aromatic rings (pentacene or borapentacene) on the reactivity of these species has been also explored. It was found that the B-doped systems are systematically much more reactive than their all-carbon counterparts from both kinetic and thermodynamic points of view. The observed trends in reactivity are quantitatively analyzed in detail using state-of-the-art methods, namely, the activation strain model of reactivity and the energy decomposition analysis method. Our calculations reveal the importance of molecular orbital interactions as the key factor responsible for the enhanced reactivity of the B-doped systems.
dc.description.filFil: Cortés, Iván. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. Consejo Nacional de Investigaciones Científicas y Técnicas (IQUIR-CONICET); Argentina.
dc.description.filFil: Cabrera Trujillo, Jorge Juan. Universidad Complutense de Madrid. Facultad de Ciencias Químicas. Departamento de Química Orgánica I y Centro de Innovación en Química Avanzada (ORFEO-CINQA); España.
dc.description.filFil: Fernández, Israel. Universidad Complutense de Madrid. Facultad de Ciencias Químicas. Departamento de Química Orgánica I y Centro de Innovación en Química Avanzada (ORFEO-CINQA); España.
dc.description.sponsorshipSpanish MICIIN: PID2019-106184GB-I00, RED2018-102387-T
dc.description.sponsorshipthe Fundación Carolina
dc.description.sponsorshipMinisterio de Educación de Argentina
dc.identifier.issn2694-247X
dc.identifier.urihttps://hdl.handle.net/2133/26848
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.publisherversionhttps://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.1c00023
dc.relation.publisherversionhttps://doi.org/10.1021/acsorginorgau.1c00023
dc.rightsopenAccess
dc.rights.holderCortés, Iván
dc.rights.holderCabrera Trujillo, Jorge Juan
dc.rights.holderFernández, Israel
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas
dc.rights.textCC BY-NC-ND 4.0 DEED Attribution-NonCommercial-NoDerivs 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectBoranthrene
dc.subjectAnthracene
dc.subjectReactivity
dc.subjectDensity functional theory calculations
dc.subjectCycloaddition
dc.titleInfluence of the CH/B replacement on the reactivity of boranthrene and related compounds
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

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