Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study

Autores
Laurella, Sergio Luis; González Sierra, Manuel; Furlong, Jorge Javier Pedro; Allegretti, Patricia Ercilia
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Substituent, temperature and solvent effects on tautomeric equilibria in several β-ketoamides have been investigated by means of nuclear magnetic resonance spectroscopy (NMR). Keto-enol equilibrium predominates over the amide-imidol one. The relative stability of the individual tautomers and the corresponding equilibrium shifts are explained consider- ing electronic and steric effects and tautomer stabilization via internal hydrogen bonds. In solution, these compounds exist mainly as ketoamide and Z-enolamide tautomers, both presenting intramolecular hydrogen bonds.
Fil: Laurella, Sergio Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: González Sierra, Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Furlong, Jorge Javier Pedro. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Allegretti, Patricia Ercilia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Materia
β-KETOAMIDES
KETO-ENOL EQUILIBRIUM
NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
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:11336/24489
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance StudyLaurella, Sergio LuisGonzález Sierra, ManuelFurlong, Jorge Javier PedroAllegretti, Patricia Erciliaβ-KETOAMIDESKETO-ENOL EQUILIBRIUMNUCLEAR MAGNETIC RESONANCE SPECTROSCOPYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Substituent, temperature and solvent effects on tautomeric equilibria in several β-ketoamides have been investigated by means of nuclear magnetic resonance spectroscopy (NMR). Keto-enol equilibrium predominates over the amide-imidol one. The relative stability of the individual tautomers and the corresponding equilibrium shifts are explained consider- ing electronic and steric effects and tautomer stabilization via internal hydrogen bonds. In solution, these compounds exist mainly as ketoamide and Z-enolamide tautomers, both presenting intramolecular hydrogen bonds.Fil: Laurella, Sergio Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: González Sierra, Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Furlong, Jorge Javier Pedro. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Allegretti, Patricia Ercilia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaScientific Research Publishing2013-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/24489Laurella, Sergio Luis; González Sierra, Manuel; Furlong, Jorge Javier Pedro; Allegretti, Patricia Ercilia; Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study; Scientific Research Publishing; Open Journal of Physical Chemistry; 3; 4; 11-2013; 138-1492162-1977CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://file.scirp.org/Html/38583.htmlinfo:eu-repo/semantics/altIdentifier/doi/10.4236/ojpc.2013.34017info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-26T09:08:26Zoai:ri.conicet.gov.ar:11336/24489instacron: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:34982025-11-26 09:08:26.562CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
title Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
spellingShingle Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
Laurella, Sergio Luis
β-KETOAMIDES
KETO-ENOL EQUILIBRIUM
NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
title_short Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
title_full Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
title_fullStr Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
title_full_unstemmed Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
title_sort Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study
dc.creator.none.fl_str_mv Laurella, Sergio Luis
González Sierra, Manuel
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
author Laurella, Sergio Luis
author_facet Laurella, Sergio Luis
González Sierra, Manuel
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
author_role author
author2 González Sierra, Manuel
Furlong, Jorge Javier Pedro
Allegretti, Patricia Ercilia
author2_role author
author
author
dc.subject.none.fl_str_mv β-KETOAMIDES
KETO-ENOL EQUILIBRIUM
NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
topic β-KETOAMIDES
KETO-ENOL EQUILIBRIUM
NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Substituent, temperature and solvent effects on tautomeric equilibria in several β-ketoamides have been investigated by means of nuclear magnetic resonance spectroscopy (NMR). Keto-enol equilibrium predominates over the amide-imidol one. The relative stability of the individual tautomers and the corresponding equilibrium shifts are explained consider- ing electronic and steric effects and tautomer stabilization via internal hydrogen bonds. In solution, these compounds exist mainly as ketoamide and Z-enolamide tautomers, both presenting intramolecular hydrogen bonds.
Fil: Laurella, Sergio Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: González Sierra, Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Furlong, Jorge Javier Pedro. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Allegretti, Patricia Ercilia. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
description Substituent, temperature and solvent effects on tautomeric equilibria in several β-ketoamides have been investigated by means of nuclear magnetic resonance spectroscopy (NMR). Keto-enol equilibrium predominates over the amide-imidol one. The relative stability of the individual tautomers and the corresponding equilibrium shifts are explained consider- ing electronic and steric effects and tautomer stabilization via internal hydrogen bonds. In solution, these compounds exist mainly as ketoamide and Z-enolamide tautomers, both presenting intramolecular hydrogen bonds.
publishDate 2013
dc.date.none.fl_str_mv 2013-11
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/11336/24489
Laurella, Sergio Luis; González Sierra, Manuel; Furlong, Jorge Javier Pedro; Allegretti, Patricia Ercilia; Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study; Scientific Research Publishing; Open Journal of Physical Chemistry; 3; 4; 11-2013; 138-149
2162-1977
CONICET Digital
CONICET
url http://hdl.handle.net/11336/24489
identifier_str_mv Laurella, Sergio Luis; González Sierra, Manuel; Furlong, Jorge Javier Pedro; Allegretti, Patricia Ercilia; Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in beta-Ketoamides: A Nuclear Magnetic Resonance Study; Scientific Research Publishing; Open Journal of Physical Chemistry; 3; 4; 11-2013; 138-149
2162-1977
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://file.scirp.org/Html/38583.html
info:eu-repo/semantics/altIdentifier/doi/10.4236/ojpc.2013.34017
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
dc.publisher.none.fl_str_mv Scientific Research Publishing
publisher.none.fl_str_mv Scientific Research Publishing
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 13.011256

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