Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species

Detalhes bibliográficos
Autor(a) principal: Firme, Caio Lima
Data de Publicação: 2013
Outros Autores: Costa, Tamires Ferreira da, Penha, Eduardo Tanoue da, Esteves, Pierre Mothé
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFRN
Texto Completo: https://repositorio.ufrn.br/jspui/handle/123456789/29216
Resumo: The highly pyramidalized molecule bisnoradamantene is extremely reactive toward nucleophiles and dienes. In this work, we studied the electronic structure of bisnoaradamantene, as well as those of its cation and dication, which are previously unreported carbonium ions. According to QTAIM and MO analysis, there is a 3c-2e bonding system in the bisnoradamantenyl cation and a 4c-2e bonding system in the bisnoradamantenyl dication. A topological study indicated that, on going from bisnoradamantene to its dication, π-bond interaction with the bridgehead carbon atom increases. Additional study of the bisnoradamantanyl dication also indicated that it has two multicenter bonding systems. Comparison of the D3BIA and NICS aromaticity indices of these molecules and other derivatives indicates that these indices are well correlated, and analysis of these indices shows that the cationic and dicationic bisnoradamantenyl species are homoaromatic.
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spelling Firme, Caio LimaCosta, Tamires Ferreira daPenha, Eduardo Tanoue daEsteves, Pierre Mothé2020-06-10T03:58:19Z2020-06-10T03:58:19Z2013-02-28FIRME, Caio Lima; COSTA, Tamires Ferreira da; PENHA, Eduardo Tanoue da; ESTEVES, Pierre Mothé. Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species. Journal Of Molecular Modeling, [s. l.], v. 19, n. 6, p. 2485-2497, 2013. ISSN 0948-5023 versão online. DOI https://doi.org/10.1007/s00894-013-1785-0. Disponível em: https://link.springer.com/article/10.1007/s00894-013-1785-0. Acesso em: 09 jun. 2020.1610-2940 (print), 0948-5023 (online)https://repositorio.ufrn.br/jspui/handle/123456789/2921610.1007/s00894-013-1785-0SpringerAttribution 3.0 Brazilhttp://creativecommons.org/licenses/by/3.0/br/info:eu-repo/semantics/openAccessQTAIMBisnoradamantenyl dicationBisnoradamanteneBisnordamantanyl dicationCarbonium ionElectronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related speciesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleThe highly pyramidalized molecule bisnoradamantene is extremely reactive toward nucleophiles and dienes. In this work, we studied the electronic structure of bisnoaradamantene, as well as those of its cation and dication, which are previously unreported carbonium ions. According to QTAIM and MO analysis, there is a 3c-2e bonding system in the bisnoradamantenyl cation and a 4c-2e bonding system in the bisnoradamantenyl dication. A topological study indicated that, on going from bisnoradamantene to its dication, π-bond interaction with the bridgehead carbon atom increases. Additional study of the bisnoradamantanyl dication also indicated that it has two multicenter bonding systems. Comparison of the D3BIA and NICS aromaticity indices of these molecules and other derivatives indicates that these indices are well correlated, and analysis of these indices shows that the cationic and dicationic bisnoradamantenyl species are homoaromatic.engreponame:Repositório Institucional da UFRNinstname:Universidade Federal do Rio Grande do Norte (UFRN)instacron:UFRNORIGINALElectronicStructuresBisnoradamantenyl_Firme_2013.pdfElectronicStructuresBisnoradamantenyl_Firme_2013.pdfapplication/pdf920417https://repositorio.ufrn.br/bitstream/123456789/29216/1/ElectronicStructuresBisnoradamantenyl_Firme_2013.pdfe047caf879964fdf9322e3bde322e04aMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.ufrn.br/bitstream/123456789/29216/2/license_rdf4d2950bda3d176f570a9f8b328dfbbefMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81484https://repositorio.ufrn.br/bitstream/123456789/29216/3/license.txte9597aa2854d128fd968be5edc8a28d9MD53TEXTElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.txtElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.txtExtracted texttext/plain50301https://repositorio.ufrn.br/bitstream/123456789/29216/4/ElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.txte2a404cdb655a5f42c63de2e4a31eb22MD54THUMBNAILElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.jpgElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.jpgGenerated Thumbnailimage/jpeg1761https://repositorio.ufrn.br/bitstream/123456789/29216/5/ElectronicStructuresBisnoradamantenyl_Firme_2013.pdf.jpg7632a74e39b2b944c19560890bdfc38eMD55123456789/292162021-02-15 16:16:00.434oai:https://repositorio.ufrn.br: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Repositório de PublicaçõesPUBhttp://repositorio.ufrn.br/oai/opendoar:2021-02-15T19:16Repositório Institucional da UFRN - Universidade Federal do Rio Grande do Norte (UFRN)false
dc.title.pt_BR.fl_str_mv Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
title Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
spellingShingle Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
Firme, Caio Lima
QTAIM
Bisnoradamantenyl dication
Bisnoradamantene
Bisnordamantanyl dication
Carbonium ion
title_short Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
title_full Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
title_fullStr Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
title_full_unstemmed Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
title_sort Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species
author Firme, Caio Lima
author_facet Firme, Caio Lima
Costa, Tamires Ferreira da
Penha, Eduardo Tanoue da
Esteves, Pierre Mothé
author_role author
author2 Costa, Tamires Ferreira da
Penha, Eduardo Tanoue da
Esteves, Pierre Mothé
author2_role author
author
author
dc.contributor.author.fl_str_mv Firme, Caio Lima
Costa, Tamires Ferreira da
Penha, Eduardo Tanoue da
Esteves, Pierre Mothé
dc.subject.por.fl_str_mv QTAIM
Bisnoradamantenyl dication
Bisnoradamantene
Bisnordamantanyl dication
Carbonium ion
topic QTAIM
Bisnoradamantenyl dication
Bisnoradamantene
Bisnordamantanyl dication
Carbonium ion
description The highly pyramidalized molecule bisnoradamantene is extremely reactive toward nucleophiles and dienes. In this work, we studied the electronic structure of bisnoaradamantene, as well as those of its cation and dication, which are previously unreported carbonium ions. According to QTAIM and MO analysis, there is a 3c-2e bonding system in the bisnoradamantenyl cation and a 4c-2e bonding system in the bisnoradamantenyl dication. A topological study indicated that, on going from bisnoradamantene to its dication, π-bond interaction with the bridgehead carbon atom increases. Additional study of the bisnoradamantanyl dication also indicated that it has two multicenter bonding systems. Comparison of the D3BIA and NICS aromaticity indices of these molecules and other derivatives indicates that these indices are well correlated, and analysis of these indices shows that the cationic and dicationic bisnoradamantenyl species are homoaromatic.
publishDate 2013
dc.date.issued.fl_str_mv 2013-02-28
dc.date.accessioned.fl_str_mv 2020-06-10T03:58:19Z
dc.date.available.fl_str_mv 2020-06-10T03:58:19Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.citation.fl_str_mv FIRME, Caio Lima; COSTA, Tamires Ferreira da; PENHA, Eduardo Tanoue da; ESTEVES, Pierre Mothé. Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species. Journal Of Molecular Modeling, [s. l.], v. 19, n. 6, p. 2485-2497, 2013. ISSN 0948-5023 versão online. DOI https://doi.org/10.1007/s00894-013-1785-0. Disponível em: https://link.springer.com/article/10.1007/s00894-013-1785-0. Acesso em: 09 jun. 2020.
dc.identifier.uri.fl_str_mv https://repositorio.ufrn.br/jspui/handle/123456789/29216
dc.identifier.issn.none.fl_str_mv 1610-2940 (print), 0948-5023 (online)
dc.identifier.doi.none.fl_str_mv 10.1007/s00894-013-1785-0
identifier_str_mv FIRME, Caio Lima; COSTA, Tamires Ferreira da; PENHA, Eduardo Tanoue da; ESTEVES, Pierre Mothé. Electronic structures of bisnoradamantenyl and bisnoradamantanyl dications and related species. Journal Of Molecular Modeling, [s. l.], v. 19, n. 6, p. 2485-2497, 2013. ISSN 0948-5023 versão online. DOI https://doi.org/10.1007/s00894-013-1785-0. Disponível em: https://link.springer.com/article/10.1007/s00894-013-1785-0. Acesso em: 09 jun. 2020.
1610-2940 (print), 0948-5023 (online)
10.1007/s00894-013-1785-0
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http://creativecommons.org/licenses/by/3.0/br/
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rights_invalid_str_mv Attribution 3.0 Brazil
http://creativecommons.org/licenses/by/3.0/br/
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