New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study

Many undergraduate organic chemistry books do not agree with the order of relative stability of alkenes towards hydrogenation reactions. Although they ascribe the stability of alkenes to the number and spatial position of the alkyl groups attached to the vinyl carbon atoms, results from the quantum...

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Principais autores: Freitas, Gutto Raffyson Silva de, Firme, Caio Lima
Formato: article
Idioma:English
Publicado em: Springer
Assuntos:
QTAIM
DFT
GVB
Alkene
Alkyne
Stability
Endereço do item:https://repositorio.ufrn.br/jspui/handle/123456789/29214
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spelling ri-123456789-292142021-02-15T19:17:23Z New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study Freitas, Gutto Raffyson Silva de Firme, Caio Lima QTAIM DFT GVB Alkene Alkyne Stability Many undergraduate organic chemistry books do not agree with the order of relative stability of alkenes towards hydrogenation reactions. Although they ascribe the stability of alkenes to the number and spatial position of the alkyl groups attached to the vinyl carbon atoms, results from the quantum theory of atoms in molecules indicate that the influence of an alkyl substituent on the stability of unsaturated hydrocarbons arises from the slight removal of electron density of the π bond, not from donation of their charge density to unsaturated carbon atoms as stated in many text books. There is an inverse relation between delocalization index—the number of shared electrons between two atoms, or Wiberg bond index of C=C bond—and the number of methyl groups attached to the vinyl carbon atoms. Electron withdrawing groups (EWGs) attached to unsaturated carbon atoms of alkenes and alkynes have two different behaviors: slight EWGs (alkyl groups) stabilize unsaturated carbon atoms while the strong EWG destabilizes the unsaturated carbon atoms. Generalized valence bond theory was also used to study the ambiguous behavior of fluorine substituents bonded to vinyl carbon atoms. 2020-06-10T03:47:37Z 2020-06-10T03:47:37Z 2013-10-17 article FREITAS, Gutto Raffyson Silva de; FIRME, Caio Lima. New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study. Journal Of Molecular Modeling, [s. l.], v. 19, n. 12, p. 5267-5276, 17 out. 2013. ISSN 0948-5023 versão online. DOI https://doi.org/10.1007/s00894-013-2022-6. Disponível em: https://link.springer.com/article/10.1007/s00894-013-2022-6. Acesso em: 09 jun. 2020. 1610-2940 (print), 0948-5023 (online) https://repositorio.ufrn.br/jspui/handle/123456789/29214 10.1007/s00894-013-2022-6 en Attribution 3.0 Brazil http://creativecommons.org/licenses/by/3.0/br/ application/pdf Springer
institution Repositório Institucional
collection RI - UFRN
language English
topic QTAIM
DFT
GVB
Alkene
Alkyne
Stability
spellingShingle QTAIM
DFT
GVB
Alkene
Alkyne
Stability
Freitas, Gutto Raffyson Silva de
Firme, Caio Lima
New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
description Many undergraduate organic chemistry books do not agree with the order of relative stability of alkenes towards hydrogenation reactions. Although they ascribe the stability of alkenes to the number and spatial position of the alkyl groups attached to the vinyl carbon atoms, results from the quantum theory of atoms in molecules indicate that the influence of an alkyl substituent on the stability of unsaturated hydrocarbons arises from the slight removal of electron density of the π bond, not from donation of their charge density to unsaturated carbon atoms as stated in many text books. There is an inverse relation between delocalization index—the number of shared electrons between two atoms, or Wiberg bond index of C=C bond—and the number of methyl groups attached to the vinyl carbon atoms. Electron withdrawing groups (EWGs) attached to unsaturated carbon atoms of alkenes and alkynes have two different behaviors: slight EWGs (alkyl groups) stabilize unsaturated carbon atoms while the strong EWG destabilizes the unsaturated carbon atoms. Generalized valence bond theory was also used to study the ambiguous behavior of fluorine substituents bonded to vinyl carbon atoms.
format article
author Freitas, Gutto Raffyson Silva de
Firme, Caio Lima
author_facet Freitas, Gutto Raffyson Silva de
Firme, Caio Lima
author_sort Freitas, Gutto Raffyson Silva de
title New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
title_short New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
title_full New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
title_fullStr New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
title_full_unstemmed New insights into the stability of alkenes and alkynes, fluoro-substituted or not: a DFT, G4, QTAIM and GVB study
title_sort new insights into the stability of alkenes and alkynes, fluoro-substituted or not: a dft, g4, qtaim and gvb study
publisher Springer
publishDate 2020
url https://repositorio.ufrn.br/jspui/handle/123456789/29214
work_keys_str_mv AT freitasguttoraffysonsilvade newinsightsintothestabilityofalkenesandalkynesfluorosubstitutedornotadftg4qtaimandgvbstudy
AT firmecaiolima newinsightsintothestabilityofalkenesandalkynesfluorosubstitutedornotadftg4qtaimandgvbstudy
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