Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene

Autores
Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M.F.
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The regioselectivity for a series of experimentally studied Diels–Alder reactions between furan derivatives and Danishefsky’s diene has been rationalized within the framework of local DFT-based descriptors (i.e. electrophilicity and nucleophilicity indexes). The importance of the solvent in the calculations has been studied. It has been shown that the relative trend of an atomic center to behave as an electrophile is affected by the medium (gas phase or benzene solution) and the basis set used in the calculation of the reactivity descriptors. The local electrophilicity (xk) and nucleophilicity (Nk) indexes properly account for the observed regioselectivity only when B3LYP/LANL2DZ and HF/LANL2DZ levels of theory have been used.
Fil: Brasca, Romina. Universidad Nacional del Litoral; Argentina
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; Argentina
Fil: Fabian, Walter M.F.. Universität Graz; Austria
Materia
Diels-Alder reactions
furan derivatives
regioselectivity
DFT-based descriptors
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:11336/103976
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s dieneBrasca, RominaKneeteman, Maria NelidaMancini, Pedro Maximo EmilioFabian, Walter M.F.Diels-Alder reactionsfuran derivativesregioselectivityDFT-based descriptorshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The regioselectivity for a series of experimentally studied Diels–Alder reactions between furan derivatives and Danishefsky’s diene has been rationalized within the framework of local DFT-based descriptors (i.e. electrophilicity and nucleophilicity indexes). The importance of the solvent in the calculations has been studied. It has been shown that the relative trend of an atomic center to behave as an electrophile is affected by the medium (gas phase or benzene solution) and the basis set used in the calculation of the reactivity descriptors. The local electrophilicity (xk) and nucleophilicity (Nk) indexes properly account for the observed regioselectivity only when B3LYP/LANL2DZ and HF/LANL2DZ levels of theory have been used.Fil: Brasca, Romina. Universidad Nacional del Litoral; ArgentinaFil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral; ArgentinaFil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; ArgentinaFil: Fabian, Walter M.F.. Universität Graz; AustriaElsevier Science2009-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/103976Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M.F.; Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene; Elsevier Science; Journal of Molecular Structure Theochem; 911; 1-3; 10-2009; 124-1310166-1280CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.elsevier.com/wps/find/journaldescription.cws_home/500851/description#descriptioninfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.theochem.2009.07.008info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:19:36Zoai:ri.conicet.gov.ar:11336/103976instacron: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:34982025-10-15 15:19:37.019CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
title Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
spellingShingle Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
Brasca, Romina
Diels-Alder reactions
furan derivatives
regioselectivity
DFT-based descriptors
title_short Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
title_full Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
title_fullStr Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
title_full_unstemmed Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
title_sort Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene
dc.creator.none.fl_str_mv Brasca, Romina
Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M.F.
author Brasca, Romina
author_facet Brasca, Romina
Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M.F.
author_role author
author2 Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M.F.
author2_role author
author
author
dc.subject.none.fl_str_mv Diels-Alder reactions
furan derivatives
regioselectivity
DFT-based descriptors
topic Diels-Alder reactions
furan derivatives
regioselectivity
DFT-based descriptors
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 regioselectivity for a series of experimentally studied Diels–Alder reactions between furan derivatives and Danishefsky’s diene has been rationalized within the framework of local DFT-based descriptors (i.e. electrophilicity and nucleophilicity indexes). The importance of the solvent in the calculations has been studied. It has been shown that the relative trend of an atomic center to behave as an electrophile is affected by the medium (gas phase or benzene solution) and the basis set used in the calculation of the reactivity descriptors. The local electrophilicity (xk) and nucleophilicity (Nk) indexes properly account for the observed regioselectivity only when B3LYP/LANL2DZ and HF/LANL2DZ levels of theory have been used.
Fil: Brasca, Romina. Universidad Nacional del Litoral; Argentina
Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; Argentina
Fil: Fabian, Walter M.F.. Universität Graz; Austria
description The regioselectivity for a series of experimentally studied Diels–Alder reactions between furan derivatives and Danishefsky’s diene has been rationalized within the framework of local DFT-based descriptors (i.e. electrophilicity and nucleophilicity indexes). The importance of the solvent in the calculations has been studied. It has been shown that the relative trend of an atomic center to behave as an electrophile is affected by the medium (gas phase or benzene solution) and the basis set used in the calculation of the reactivity descriptors. The local electrophilicity (xk) and nucleophilicity (Nk) indexes properly account for the observed regioselectivity only when B3LYP/LANL2DZ and HF/LANL2DZ levels of theory have been used.
publishDate 2009
dc.date.none.fl_str_mv 2009-10
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/11336/103976
Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M.F.; Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene; Elsevier Science; Journal of Molecular Structure Theochem; 911; 1-3; 10-2009; 124-131
0166-1280
CONICET Digital
CONICET
url http://hdl.handle.net/11336/103976
identifier_str_mv Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M.F.; Theoretical explanation of the regioselectivity of polar cycloaddition reactions between furan derivatives and Danishefsky’s diene; Elsevier Science; Journal of Molecular Structure Theochem; 911; 1-3; 10-2009; 124-131
0166-1280
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.elsevier.com/wps/find/journaldescription.cws_home/500851/description#description
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.theochem.2009.07.008
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 13.22299

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