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

Autores
Cortés, Iván; Cabrera Trujillo, Jorge Juan; Fernández, Israel
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The 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.
Fil: Cortés, Iván. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Cabrera Trujillo, Jorge Juan. Universidad Complutense de Madrid; España
Fil: Fernández, Israel. Universidad Complutense de Madrid; España
Materia
BORANTHRENE
ANTHRACENE
REACTIVITY
DENSITY FUNCTIONAL THEORY CALCULATIONS
CYCLOADDITION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/166176
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Influence of the CH/B replacement on the reactivity of boranthrene and related compoundsCortés, IvánCabrera Trujillo, Jorge JuanFernández, IsraelBORANTHRENEANTHRACENEREACTIVITYDENSITY FUNCTIONAL THEORY CALCULATIONSCYCLOADDITIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The 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.Fil: Cortés, Iván. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Cabrera Trujillo, Jorge Juan. Universidad Complutense de Madrid; EspañaFil: Fernández, Israel. Universidad Complutense de Madrid; EspañaAmerican Chemical Society2021-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/166176Cortés, Iván; Cabrera Trujillo, Jorge Juan; Fernández, Israel; Influence of the CH/B replacement on the reactivity of boranthrene and related compounds; American Chemical Society; ACS Organic & Inorganic Au; 2; 1; 10-2021; 44-522694-247XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsorginorgau.1c00023info:eu-repo/semantics/altIdentifier/doi/10.1021/acsorginorgau.1c00023info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:19:54Zoai:ri.conicet.gov.ar:11336/166176instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:19:54.638CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
title Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
spellingShingle Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
Cortés, Iván
BORANTHRENE
ANTHRACENE
REACTIVITY
DENSITY FUNCTIONAL THEORY CALCULATIONS
CYCLOADDITION
title_short Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
title_full Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
title_fullStr Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
title_full_unstemmed Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
title_sort Influence of the CH/B replacement on the reactivity of boranthrene and related compounds
dc.creator.none.fl_str_mv Cortés, Iván
Cabrera Trujillo, Jorge Juan
Fernández, Israel
author Cortés, Iván
author_facet Cortés, Iván
Cabrera Trujillo, Jorge Juan
Fernández, Israel
author_role author
author2 Cabrera Trujillo, Jorge Juan
Fernández, Israel
author2_role author
author
dc.subject.none.fl_str_mv BORANTHRENE
ANTHRACENE
REACTIVITY
DENSITY FUNCTIONAL THEORY CALCULATIONS
CYCLOADDITION
topic BORANTHRENE
ANTHRACENE
REACTIVITY
DENSITY FUNCTIONAL THEORY CALCULATIONS
CYCLOADDITION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The 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.
Fil: Cortés, Iván. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Cabrera Trujillo, Jorge Juan. Universidad Complutense de Madrid; España
Fil: Fernández, Israel. Universidad Complutense de Madrid; España
description The 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.
publishDate 2021
dc.date.none.fl_str_mv 2021-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/166176
Cortés, Iván; Cabrera Trujillo, Jorge Juan; Fernández, Israel; Influence of the CH/B replacement on the reactivity of boranthrene and related compounds; American Chemical Society; ACS Organic & Inorganic Au; 2; 1; 10-2021; 44-52
2694-247X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/166176
identifier_str_mv Cortés, Iván; Cabrera Trujillo, Jorge Juan; Fernández, Israel; Influence of the CH/B replacement on the reactivity of boranthrene and related compounds; American Chemical Society; ACS Organic & Inorganic Au; 2; 1; 10-2021; 44-52
2694-247X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsorginorgau.1c00023
info:eu-repo/semantics/altIdentifier/doi/10.1021/acsorginorgau.1c00023
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.8982525

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