Identification of carbonium and carbenium ions by QTAIM
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000300020 |
Resumo: | The Gassman-Fentiman tool of increasing electron demand was used to identify carbonium and carbenium ions. Nonetheless, due to its ambiguous understanding, it was pivot of a historical dispute. We applied the Quantum Theory of Atoms in Molecules (QTAIM) metodology to characterize the carbonium and carbenium ions on an easier and more effective way. By comparing selected topological information of reference carbenium ions the QTAIM metodology can be used to evaluate whether a carbocation is classical or not. In addition, it is possible to rank a set of carbonium ions in order of their corresponding σ or π delocalization. There are few differences between our QTAIM-based model and Gassman-Fentiman tool. Unlike Gassman-Fentiman tool results, 7-anisyl-7-norbornenyl and 2-anisyl-2-norbornyl cations are non-classical, although they are the least nonclassical ions in their corresponding set of studied cations. |
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Identification of carbonium and carbenium ions by QTAIMnorbornyl cationnorbornenyl cationQTAIMcarbonium ioncarbenium ionThe Gassman-Fentiman tool of increasing electron demand was used to identify carbonium and carbenium ions. Nonetheless, due to its ambiguous understanding, it was pivot of a historical dispute. We applied the Quantum Theory of Atoms in Molecules (QTAIM) metodology to characterize the carbonium and carbenium ions on an easier and more effective way. By comparing selected topological information of reference carbenium ions the QTAIM metodology can be used to evaluate whether a carbocation is classical or not. In addition, it is possible to rank a set of carbonium ions in order of their corresponding σ or π delocalization. There are few differences between our QTAIM-based model and Gassman-Fentiman tool. Unlike Gassman-Fentiman tool results, 7-anisyl-7-norbornenyl and 2-anisyl-2-norbornyl cations are non-classical, although they are the least nonclassical ions in their corresponding set of studied cations.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000300020Journal of the Brazilian Chemical Society v.20 n.3 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000300020info:eu-repo/semantics/openAccessFirme,Caio L.Antunes,O. A. C.Esteves,Pierre M.eng2009-05-25T00:00:00Zoai:scielo:S0103-50532009000300020Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-05-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Identification of carbonium and carbenium ions by QTAIM |
title |
Identification of carbonium and carbenium ions by QTAIM |
spellingShingle |
Identification of carbonium and carbenium ions by QTAIM Firme,Caio L. norbornyl cation norbornenyl cation QTAIM carbonium ion carbenium ion |
title_short |
Identification of carbonium and carbenium ions by QTAIM |
title_full |
Identification of carbonium and carbenium ions by QTAIM |
title_fullStr |
Identification of carbonium and carbenium ions by QTAIM |
title_full_unstemmed |
Identification of carbonium and carbenium ions by QTAIM |
title_sort |
Identification of carbonium and carbenium ions by QTAIM |
author |
Firme,Caio L. |
author_facet |
Firme,Caio L. Antunes,O. A. C. Esteves,Pierre M. |
author_role |
author |
author2 |
Antunes,O. A. C. Esteves,Pierre M. |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Firme,Caio L. Antunes,O. A. C. Esteves,Pierre M. |
dc.subject.por.fl_str_mv |
norbornyl cation norbornenyl cation QTAIM carbonium ion carbenium ion |
topic |
norbornyl cation norbornenyl cation QTAIM carbonium ion carbenium ion |
description |
The Gassman-Fentiman tool of increasing electron demand was used to identify carbonium and carbenium ions. Nonetheless, due to its ambiguous understanding, it was pivot of a historical dispute. We applied the Quantum Theory of Atoms in Molecules (QTAIM) metodology to characterize the carbonium and carbenium ions on an easier and more effective way. By comparing selected topological information of reference carbenium ions the QTAIM metodology can be used to evaluate whether a carbocation is classical or not. In addition, it is possible to rank a set of carbonium ions in order of their corresponding σ or π delocalization. There are few differences between our QTAIM-based model and Gassman-Fentiman tool. Unlike Gassman-Fentiman tool results, 7-anisyl-7-norbornenyl and 2-anisyl-2-norbornyl cations are non-classical, although they are the least nonclassical ions in their corresponding set of studied cations. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-01-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000300020 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000300020 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532009000300020 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.20 n.3 2009 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318169797427200 |