What defines electrophilicity in carbonyl compounds

The origin of the electrophilicity of a series of cyclohexanones and benzaldehydes is investigated using the activation strain model and quantitative Kohn–Sham molecular orbital (MO) theory. We find that this electrophilicity is mainly determined by the electrostatic attractions between the carbonyl...

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Detalles Bibliográficos
Autores: Bickelhaupt, F. Matthias, Fernández López, Israel
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/109222
Acceso en línea:https://hdl.handle.net/20.500.14352/109222
Access Level:acceso abierto
Palabra clave:Química orgánica (Química)
2306 Química Orgánica
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spelling What defines electrophilicity in carbonyl compoundsBickelhaupt, F. MatthiasFernández López, IsraelQuímica orgánica (Química)2306 Química OrgánicaThe origin of the electrophilicity of a series of cyclohexanones and benzaldehydes is investigated using the activation strain model and quantitative Kohn–Sham molecular orbital (MO) theory. We find that this electrophilicity is mainly determined by the electrostatic attractions between the carbonyl compound and the nucleophile (cyanide) along the entire reaction coordinate. Donor–acceptor frontier molecular orbital interactions, on which the current rationale behind electrophilicity trends is based, appear to have little or no significant influence on the reactivity of these carbonyl compounds.Royal Society of ChemistryUniversidad Complutense de Madrid20242024-01-0120242024-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/109222reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)InglésengMCIN AEI 10.13039 PID2019-106184GB-I00MCIN AEI 10.13039 PID2022- 139318NB-I00MCIN AEI 10.13039 RED2022-134287-Topen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1092222026-06-02T12:44:21Z
dc.title.none.fl_str_mv What defines electrophilicity in carbonyl compounds
title What defines electrophilicity in carbonyl compounds
spellingShingle What defines electrophilicity in carbonyl compounds
Bickelhaupt, F. Matthias
Química orgánica (Química)
2306 Química Orgánica
title_short What defines electrophilicity in carbonyl compounds
title_full What defines electrophilicity in carbonyl compounds
title_fullStr What defines electrophilicity in carbonyl compounds
title_full_unstemmed What defines electrophilicity in carbonyl compounds
title_sort What defines electrophilicity in carbonyl compounds
dc.creator.none.fl_str_mv Bickelhaupt, F. Matthias
Fernández López, Israel
author Bickelhaupt, F. Matthias
author_facet Bickelhaupt, F. Matthias
Fernández López, Israel
author_role author
author2 Fernández López, Israel
author2_role author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv Química orgánica (Química)
2306 Química Orgánica
topic Química orgánica (Química)
2306 Química Orgánica
description The origin of the electrophilicity of a series of cyclohexanones and benzaldehydes is investigated using the activation strain model and quantitative Kohn–Sham molecular orbital (MO) theory. We find that this electrophilicity is mainly determined by the electrostatic attractions between the carbonyl compound and the nucleophile (cyanide) along the entire reaction coordinate. Donor–acceptor frontier molecular orbital interactions, on which the current rationale behind electrophilicity trends is based, appear to have little or no significant influence on the reactivity of these carbonyl compounds.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-01-01
2024
2024-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/109222
url https://hdl.handle.net/20.500.14352/109222
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv MCIN AEI 10.13039 PID2019-106184GB-I00
MCIN AEI 10.13039 PID2022- 139318NB-I00
MCIN AEI 10.13039 RED2022-134287-T
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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