dc.creator | Laurella, Sergio Luis | |
dc.date.accessioned | 2021-05-07T17:30:29Z | |
dc.date.accessioned | 2022-10-15T10:43:33Z | |
dc.date.available | 2021-05-07T17:30:29Z | |
dc.date.available | 2022-10-15T10:43:33Z | |
dc.date.created | 2021-05-07T17:30:29Z | |
dc.date.issued | 2012-08 | |
dc.identifier | Laurella, Sergio Luis; Analysis of Tautomerism in beta-Ketobutanamides by Nuclear Magnetic Resonance: Substituent, Temperature and Solvent Effects; Lifescience Global; Journal of Applied Solution Chemistry and Modeling; 1; 1; 8-2012; 1-7 | |
dc.identifier | 1929-5030 | |
dc.identifier | http://hdl.handle.net/11336/131681 | |
dc.identifier | CONICET Digital | |
dc.identifier | CONICET | |
dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/4376969 | |
dc.description.abstract | β-ketoamides are versatile intermediates for the synthesis of several heterocycles and they are also relevant compounds in biological systems, with their tautomeric equilibria being a crucial aspect to be studied in order to understand their chemical and biological behaviour. Tautomeric equilibria of a series of β-ketobutanamides were analyzed by means of 1HNMR, determining that ketoamide and Z-enolamide are the main tautomeric species in solution, both presenting internal hydrogen bonds. Keto-enol equilibrium predominates over other possible tautomerisms (e.g. amide-imidol). The enol tautomer appears to be favoured by electron withdrawing substituents and non-protic solvents. Thermodynamic parameters ΔH and ΔS were determined in CDCl3 and DMSO-d6, showing that the keto-enol equilibria are exothermic and require a molecule order increase. | |
dc.language | eng | |
dc.publisher | Lifescience Global | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/https://www.lifescienceglobal.com/pms/index.php/JASCM/article/view/527 | |
dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | |
dc.rights | info:eu-repo/semantics/openAccess | |
dc.subject | BETA-KETOAMIDES | |
dc.subject | KETO-ENOL EQUILIBRIUM | |
dc.subject | NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY | |
dc.title | Analysis of Tautomerism in beta-Ketobutanamides by Nuclear Magnetic Resonance: Substituent, Temperature and Solvent Effects | |
dc.type | info:eu-repo/semantics/article | |
dc.type | info:ar-repo/semantics/artículo | |
dc.type | info:eu-repo/semantics/publishedVersion | |