NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides

Autores
Pedersoli, Susimaire; Dos Santos, Francisco P.; Rittner, Roberto; Contreras, Ruben Horacio; Tormena, Cláudio F.
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work 3JCH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for α-X-acetamides (X = F, Cl, Br and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of 3JCH SSCCs and its potential as a probe to study the stereochemical properties of the XH 2C group are discussed. Copyright © 2008 John Wiley & Sons, Ltd.
Fil: Pedersoli, Susimaire. Universidade Estadual de Campinas; Brasil
Fil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; Brasil
Fil: Rittner, Roberto. Universidade Estadual de Campinas; Brasil
Fil: Contreras, Ruben Horacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Física de Buenos Aires. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Física de Buenos Aires; Argentina
Fil: Tormena, Cláudio F.. Universidade Estadual de Campinas; Brasil
Materia
3jch Couplings
Fc Transmission
Negative Hyperconjugative Interactions
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:11336/61994
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamidesPedersoli, SusimaireDos Santos, Francisco P.Rittner, RobertoContreras, Ruben HoracioTormena, Cláudio F.3jch CouplingsFc TransmissionNegative Hyperconjugative Interactionshttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1In this work 3JCH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for α-X-acetamides (X = F, Cl, Br and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of 3JCH SSCCs and its potential as a probe to study the stereochemical properties of the XH 2C group are discussed. Copyright © 2008 John Wiley & Sons, Ltd.Fil: Pedersoli, Susimaire. Universidade Estadual de Campinas; BrasilFil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; BrasilFil: Rittner, Roberto. Universidade Estadual de Campinas; BrasilFil: Contreras, Ruben Horacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Física de Buenos Aires. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Física de Buenos Aires; ArgentinaFil: Tormena, Cláudio F.. Universidade Estadual de Campinas; BrasilJohn Wiley & Sons Ltd2008-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/61994Pedersoli, Susimaire; Dos Santos, Francisco P.; Rittner, Roberto; Contreras, Ruben Horacio; Tormena, Cláudio F.; NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides; John Wiley & Sons Ltd; Magnetic Resonance in Chemistry; 46; 3; 3-2008; 202-2050749-1581CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/mrc.2158info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/mrc.2158info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T10:44:08Zoai:ri.conicet.gov.ar:11336/61994instacron: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:34982025-09-17 10:44:09.03CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
title NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
spellingShingle NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
Pedersoli, Susimaire
3jch Couplings
Fc Transmission
Negative Hyperconjugative Interactions
title_short NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
title_full NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
title_fullStr NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
title_full_unstemmed NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
title_sort NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides
dc.creator.none.fl_str_mv Pedersoli, Susimaire
Dos Santos, Francisco P.
Rittner, Roberto
Contreras, Ruben Horacio
Tormena, Cláudio F.
author Pedersoli, Susimaire
author_facet Pedersoli, Susimaire
Dos Santos, Francisco P.
Rittner, Roberto
Contreras, Ruben Horacio
Tormena, Cláudio F.
author_role author
author2 Dos Santos, Francisco P.
Rittner, Roberto
Contreras, Ruben Horacio
Tormena, Cláudio F.
author2_role author
author
author
author
dc.subject.none.fl_str_mv 3jch Couplings
Fc Transmission
Negative Hyperconjugative Interactions
topic 3jch Couplings
Fc Transmission
Negative Hyperconjugative Interactions
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.3
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work 3JCH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for α-X-acetamides (X = F, Cl, Br and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of 3JCH SSCCs and its potential as a probe to study the stereochemical properties of the XH 2C group are discussed. Copyright © 2008 John Wiley & Sons, Ltd.
Fil: Pedersoli, Susimaire. Universidade Estadual de Campinas; Brasil
Fil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; Brasil
Fil: Rittner, Roberto. Universidade Estadual de Campinas; Brasil
Fil: Contreras, Ruben Horacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Física de Buenos Aires. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Física de Buenos Aires; Argentina
Fil: Tormena, Cláudio F.. Universidade Estadual de Campinas; Brasil
description In this work 3JCH spin-spin coupling constants (SSCCs) for the cis- and trans-conformers for α-X-acetamides (X = F, Cl, Br and CN) (1-4) were studied in detail since they were found to be notably different for both conformers. These differences are rationalized as originating in the changes of the strong negative hyperconjugative interactions that take place within the carbonyl group. Such changes are found to depend not only on conformation, but also on solvent. For the cis-conformers there is a close proximity between the X-substituent and the in-plane oxygen lone pair of pure p character, which affects notably their respective negative hyperconjugative interactions. Both the efficiency for transmitting the Fermi contact (FC) term through the coupling pathway of 3JCH SSCCs and its potential as a probe to study the stereochemical properties of the XH 2C group are discussed. Copyright © 2008 John Wiley & Sons, Ltd.
publishDate 2008
dc.date.none.fl_str_mv 2008-03
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/11336/61994
Pedersoli, Susimaire; Dos Santos, Francisco P.; Rittner, Roberto; Contreras, Ruben Horacio; Tormena, Cláudio F.; NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides; John Wiley & Sons Ltd; Magnetic Resonance in Chemistry; 46; 3; 3-2008; 202-205
0749-1581
CONICET Digital
CONICET
url http://hdl.handle.net/11336/61994
identifier_str_mv Pedersoli, Susimaire; Dos Santos, Francisco P.; Rittner, Roberto; Contreras, Ruben Horacio; Tormena, Cláudio F.; NMR spin-spin couplings involving nuclei in the neighborhood of a carbonyl group. 3JCH couplings in α-substituted acetamides; John Wiley & Sons Ltd; Magnetic Resonance in Chemistry; 46; 3; 3-2008; 202-205
0749-1581
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/mrc.2158
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/mrc.2158
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 John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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 13.000565

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