Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines

Autores
Jios, Jorge Luis; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Magiera, Damian; Duddeck, Helmut
Año de publicación
2002
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
1 H, 13 C and 15 N NMR spectra of twenty substituted N-phenoxyethylanilines 1Ð20 were completely and unambiguously assigned using a combination of both homo- and heteronuclear (gs-COSY), 1 H detected heteronuclear one-bond (gs-HMQC) and long-range (gsHMBC) gradient-selected correlation experiments. Correlations between chemical shifts and substituent constants are analyzed separately for both phenyl rings using variable substituents para to the fixed substituent -OCH2CH2NHC6H5 (series I) and -NHCH2CH2OC6H5 (series II), respectively. The correlation coefficient for chemical shifts vs. a linear combination of inductive and resonance substituent constants is high and improves when only the six values, corresponding to each para-monosubstituted series, were used. For nitrogen chemical shifts excellent linear dependences were obtained. The results show that the ethylene chain is not able to transmit the substituent effect from one aromatic ring to the other.
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Magiera, Damian. Universität Hannover. Institut für Organische Chemie; Alemania
Fil: Duddeck, Helmut. Universität Hannover. Institut für Organische Chemie; Alemania
Materia
Nmr Data
Phenoxyethylanilines
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:11336/62696
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-PhenoxyethylanilinesJios, Jorge LuisRomanelli, Gustavo PabloAutino, Juan CarlosMagiera, DamianDuddeck, HelmutNmr DataPhenoxyethylanilinesSubstituent Effectshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/11 H, 13 C and 15 N NMR spectra of twenty substituted N-phenoxyethylanilines 1Ð20 were completely and unambiguously assigned using a combination of both homo- and heteronuclear (gs-COSY), 1 H detected heteronuclear one-bond (gs-HMQC) and long-range (gsHMBC) gradient-selected correlation experiments. Correlations between chemical shifts and substituent constants are analyzed separately for both phenyl rings using variable substituents para to the fixed substituent -OCH2CH2NHC6H5 (series I) and -NHCH2CH2OC6H5 (series II), respectively. The correlation coefficient for chemical shifts vs. a linear combination of inductive and resonance substituent constants is high and improves when only the six values, corresponding to each para-monosubstituted series, were used. For nitrogen chemical shifts excellent linear dependences were obtained. The results show that the ethylene chain is not able to transmit the substituent effect from one aromatic ring to the other.Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Magiera, Damian. Universität Hannover. Institut für Organische Chemie; AlemaniaFil: Duddeck, Helmut. Universität Hannover. Institut für Organische Chemie; AlemaniaDe Gruyter2002-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62696Jios, Jorge Luis; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Magiera, Damian; Duddeck, Helmut; Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines; De Gruyter; Zeitschrift für Naturforschung Section B - A Journal of Chemical Sciences; 57; 2; 1-2-2002; 226-2320932-07761865-7117CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1515/znb-2002-0214info:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/view/j/znb.2002.57.issue-2/znb-2002-0214/znb-2002-0214.xmlinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:06:57Zoai:ri.conicet.gov.ar:11336/62696instacron: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:34982025-09-29 10:06:57.756CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
title Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
spellingShingle Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
Jios, Jorge Luis
Nmr Data
Phenoxyethylanilines
Substituent Effects
title_short Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
title_full Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
title_fullStr Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
title_full_unstemmed Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
title_sort Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines
dc.creator.none.fl_str_mv Jios, Jorge Luis
Romanelli, Gustavo Pablo
Autino, Juan Carlos
Magiera, Damian
Duddeck, Helmut
author Jios, Jorge Luis
author_facet Jios, Jorge Luis
Romanelli, Gustavo Pablo
Autino, Juan Carlos
Magiera, Damian
Duddeck, Helmut
author_role author
author2 Romanelli, Gustavo Pablo
Autino, Juan Carlos
Magiera, Damian
Duddeck, Helmut
author2_role author
author
author
author
dc.subject.none.fl_str_mv Nmr Data
Phenoxyethylanilines
Substituent Effects
topic Nmr Data
Phenoxyethylanilines
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 1 H, 13 C and 15 N NMR spectra of twenty substituted N-phenoxyethylanilines 1Ð20 were completely and unambiguously assigned using a combination of both homo- and heteronuclear (gs-COSY), 1 H detected heteronuclear one-bond (gs-HMQC) and long-range (gsHMBC) gradient-selected correlation experiments. Correlations between chemical shifts and substituent constants are analyzed separately for both phenyl rings using variable substituents para to the fixed substituent -OCH2CH2NHC6H5 (series I) and -NHCH2CH2OC6H5 (series II), respectively. The correlation coefficient for chemical shifts vs. a linear combination of inductive and resonance substituent constants is high and improves when only the six values, corresponding to each para-monosubstituted series, were used. For nitrogen chemical shifts excellent linear dependences were obtained. The results show that the ethylene chain is not able to transmit the substituent effect from one aromatic ring to the other.
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Magiera, Damian. Universität Hannover. Institut für Organische Chemie; Alemania
Fil: Duddeck, Helmut. Universität Hannover. Institut für Organische Chemie; Alemania
description 1 H, 13 C and 15 N NMR spectra of twenty substituted N-phenoxyethylanilines 1Ð20 were completely and unambiguously assigned using a combination of both homo- and heteronuclear (gs-COSY), 1 H detected heteronuclear one-bond (gs-HMQC) and long-range (gsHMBC) gradient-selected correlation experiments. Correlations between chemical shifts and substituent constants are analyzed separately for both phenyl rings using variable substituents para to the fixed substituent -OCH2CH2NHC6H5 (series I) and -NHCH2CH2OC6H5 (series II), respectively. The correlation coefficient for chemical shifts vs. a linear combination of inductive and resonance substituent constants is high and improves when only the six values, corresponding to each para-monosubstituted series, were used. For nitrogen chemical shifts excellent linear dependences were obtained. The results show that the ethylene chain is not able to transmit the substituent effect from one aromatic ring to the other.
publishDate 2002
dc.date.none.fl_str_mv 2002-02-01
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/11336/62696
Jios, Jorge Luis; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Magiera, Damian; Duddeck, Helmut; Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines; De Gruyter; Zeitschrift für Naturforschung Section B - A Journal of Chemical Sciences; 57; 2; 1-2-2002; 226-232
0932-0776
1865-7117
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62696
identifier_str_mv Jios, Jorge Luis; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Magiera, Damian; Duddeck, Helmut; Multinuclear (1H, 13C and 15N) Magnetic Resonance Spectroscopy and Substituent Effects on N-Phenoxyethylanilines; De Gruyter; Zeitschrift für Naturforschung Section B - A Journal of Chemical Sciences; 57; 2; 1-2-2002; 226-232
0932-0776
1865-7117
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1515/znb-2002-0214
info:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/view/j/znb.2002.57.issue-2/znb-2002-0214/znb-2002-0214.xml
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 De Gruyter
publisher.none.fl_str_mv De Gruyter
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 13.070432

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