Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives

Autores
Favaro, Denize C.; Ducati, Lucas C.; Dos Santos, Francisco P.; Contreras, Ruben Horacio; Tormena, Claudio F.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society.
Fil: Favaro, Denize C.. Universidade Estadual de Campinas; Brasil
Fil: Ducati, Lucas C.. Universidade Estadual de Campinas; Brasil
Fil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; Brasil
Fil: Contreras, Ruben Horacio. Universidad de Buenos Aires; Argentina. 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, Claudio F.. Universidade Estadual de Campinas; Brasil
Materia
Vicinal 3-J(Ch) Couplings
Stereochemical Dependence
Proximity Interaction
Substituent Effect on Rear Lobe Interaction
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:11336/56650

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spelling Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivativesFavaro, Denize C.Ducati, Lucas C.Dos Santos, Francisco P.Contreras, Ruben HoracioTormena, Claudio F.Vicinal 3-J(Ch) CouplingsStereochemical DependenceProximity InteractionSubstituent Effect on Rear Lobe Interactionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society.Fil: Favaro, Denize C.. Universidade Estadual de Campinas; BrasilFil: Ducati, Lucas C.. Universidade Estadual de Campinas; BrasilFil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; BrasilFil: Contreras, Ruben Horacio. Universidad de Buenos Aires; Argentina. 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, Claudio F.. Universidade Estadual de Campinas; BrasilAmerican Chemical Society2011-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/56650Favaro, Denize C.; Ducati, Lucas C.; Dos Santos, Francisco P.; Contreras, Ruben Horacio; Tormena, Claudio F.; Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives; American Chemical Society; Journal of Physical Chemistry A; 115; 50; 11-2011; 14539-145451089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp2083456info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:57:09Zoai:ri.conicet.gov.ar:11336/56650instacron: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:34982025-10-22 11:57:10.154CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
spellingShingle Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
Favaro, Denize C.
Vicinal 3-J(Ch) Couplings
Stereochemical Dependence
Proximity Interaction
Substituent Effect on Rear Lobe Interaction
title_short Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_full Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_fullStr Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_full_unstemmed Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
title_sort Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives
dc.creator.none.fl_str_mv Favaro, Denize C.
Ducati, Lucas C.
Dos Santos, Francisco P.
Contreras, Ruben Horacio
Tormena, Claudio F.
author Favaro, Denize C.
author_facet Favaro, Denize C.
Ducati, Lucas C.
Dos Santos, Francisco P.
Contreras, Ruben Horacio
Tormena, Claudio F.
author_role author
author2 Ducati, Lucas C.
Dos Santos, Francisco P.
Contreras, Ruben Horacio
Tormena, Claudio F.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Vicinal 3-J(Ch) Couplings
Stereochemical Dependence
Proximity Interaction
Substituent Effect on Rear Lobe Interaction
topic Vicinal 3-J(Ch) Couplings
Stereochemical Dependence
Proximity Interaction
Substituent Effect on Rear Lobe Interaction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society.
Fil: Favaro, Denize C.. Universidade Estadual de Campinas; Brasil
Fil: Ducati, Lucas C.. Universidade Estadual de Campinas; Brasil
Fil: Dos Santos, Francisco P.. Universidade Estadual de Campinas; Brasil
Fil: Contreras, Ruben Horacio. Universidad de Buenos Aires; Argentina. 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, Claudio F.. Universidade Estadual de Campinas; Brasil
description Theoretical and experimental studies on 3J C2H6eq NMR spin - spin coupling constants in both the 2-X-4-t-butyl-cyclohexanone (X = H, CH 3, F, Cl, and Br) and in their alcohol derivatives series are reported. Results thus found are rationalized in terms of the transmission of the Fermi contact contribution to such couplings. To this end, dependencies of 3J C2H6eq couplings versus the C 2 - C 1 - C 6 angle are compared in both series for equatorial and axial X orientations. The main trend is described in terms of the rear lobes interaction. Besides, for X = halogen atom in equatorial orientation a rather strong interaction between oxygen and halogen lone pairs is observed, and its influence on 3J C2H6eq couplings is discussed and rationalized in terms of different Fermi contact transmission pathways. (Figure presented) © 2011 American Chemical Society.
publishDate 2011
dc.date.none.fl_str_mv 2011-11
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/11336/56650
Favaro, Denize C.; Ducati, Lucas C.; Dos Santos, Francisco P.; Contreras, Ruben Horacio; Tormena, Claudio F.; Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives; American Chemical Society; Journal of Physical Chemistry A; 115; 50; 11-2011; 14539-14545
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/56650
identifier_str_mv Favaro, Denize C.; Ducati, Lucas C.; Dos Santos, Francisco P.; Contreras, Ruben Horacio; Tormena, Claudio F.; Stereochemical dependence of 3J CH coupling constants in 2-substituted 4-t-butyl-cyclohexanone and their alcohol derivatives; American Chemical Society; Journal of Physical Chemistry A; 115; 50; 11-2011; 14539-14545
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jp2083456
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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