Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-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.
Facultad de Ciencias Exactas
Laboratorio de Estudio de Compuestos Orgánicos (LADECOR)
Materia
Química
β-Ketoamides
Keto-Enol Equilibrium
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/81150
Acceder
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network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance StudyLaurella, Sergio LuisGonzález Sierra, ManuelFurlong, Jorge Javier PedroAllegretti, Patricia ErciliaQuímicaβ-KetoamidesKeto-Enol EquilibriumSubstituent, 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.Facultad de Ciencias ExactasLaboratorio de Estudio de Compuestos Orgánicos (LADECOR)2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf138-149http://sedici.unlp.edu.ar/handle/10915/81150enginfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-17T09:57:47Zoai:sedici.unlp.edu.ar:10915/81150Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-17 09:57:48.017SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
title Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
spellingShingle Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
Laurella, Sergio Luis
Química
β-Ketoamides
Keto-Enol Equilibrium
title_short Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
title_full Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
title_fullStr Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
title_full_unstemmed Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-Ketoamides: A Nuclear Magnetic Resonance Study
title_sort Substituent, Temperature and Solvent Effects on the Keto-Enol Equilibrium in β-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 Química
β-Ketoamides
Keto-Enol Equilibrium
topic Química
β-Ketoamides
Keto-Enol Equilibrium
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.
Facultad de Ciencias Exactas
Laboratorio de Estudio de Compuestos Orgánicos (LADECOR)
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
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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://sedici.unlp.edu.ar/handle/10915/81150
url http://sedici.unlp.edu.ar/handle/10915/81150
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
138-149
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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score 13.000565

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