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
.jpg)
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/81150
Ver los metadatos del registro completo
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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:UNLP2025-10-29T15:20:06Zoai: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:13292025-10-29 15:20:06.969SEDICI (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 |
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article |
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http://sedici.unlp.edu.ar/handle/10915/81150 |
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| dc.language.none.fl_str_mv |
eng |
| language |
eng |
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info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) |
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openAccess |
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http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) |
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application/pdf 138-149 |
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