In Silico Study on Chemical Properties and Reactivity of Enal Derivatives

Autores
Borosky, Gabriela Leonor; Laali, Kenneth K.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis-silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio- and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
Materia
Computational Chemistry
Enals
Reaction Mechanisms
Silicon
Substituent Effects
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/50103
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50103
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling In Silico Study on Chemical Properties and Reactivity of Enal DerivativesBorosky, Gabriela LeonorLaali, Kenneth K.Computational ChemistryEnalsReaction MechanismsSiliconSubstituent Effectshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis-silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio- and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Laali, Kenneth K.. University of North Florida; Estados UnidosWiley VCH Verlag2015-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/50103Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico Study on Chemical Properties and Reactivity of Enal Derivatives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 30; 10-2015; 6615-66231434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201500853info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201500853info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-08-25T14:49:08Zoai:ri.conicet.gov.ar:11336/50103instacron: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:34982026-08-25 14:49:09.087CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
title In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
spellingShingle In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
Borosky, Gabriela Leonor
Computational Chemistry
Enals
Reaction Mechanisms
Silicon
Substituent Effects
title_short In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
title_full In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
title_fullStr In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
title_full_unstemmed In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
title_sort In Silico Study on Chemical Properties and Reactivity of Enal Derivatives
dc.creator.none.fl_str_mv Borosky, Gabriela Leonor
Laali, Kenneth K.
author Borosky, Gabriela Leonor
author_facet Borosky, Gabriela Leonor
Laali, Kenneth K.
author_role author
author2 Laali, Kenneth K.
author2_role author
dc.subject.none.fl_str_mv Computational Chemistry
Enals
Reaction Mechanisms
Silicon
Substituent Effects
topic Computational Chemistry
Enals
Reaction Mechanisms
Silicon
Substituent Effects
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 chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis-silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio- and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.
Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Laali, Kenneth K.. University of North Florida; Estados Unidos
description The chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis-silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio- and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
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/11336/50103
Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico Study on Chemical Properties and Reactivity of Enal Derivatives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 30; 10-2015; 6615-6623
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50103
identifier_str_mv Borosky, Gabriela Leonor; Laali, Kenneth K.; In Silico Study on Chemical Properties and Reactivity of Enal Derivatives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 30; 10-2015; 6615-6623
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201500853
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201500853
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.334379

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