Artículo
NMR and computational studies on tautomerism of 3-hydroxy-2-(2-thienylcarbonyl) cyclohex-2-en-1-one
Fecha de publicación:
12/2013
Editorial:
Elsevier Science
Revista:
Journal of Molecular Structure
ISSN:
0022-2860
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The tautomeric system of 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one 1 has been investigated by NMR spectroscopy between 224 and 298 K. At all temperatures an endocyclic enol tautomer was the major isomer; however, at low temperatures two other enol isomers were found. Conformational search of the potential energy surfaces of all tautomers of cyclohexenone 1 was also carried out. Extensive calculations were performed for two triketones and four cis-endocyclic double bond enol tautomers with the lowest energies. Syntheses of 3-methoxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one 2 and 2-benzoyl-3-hydroxycyclohex-2-en-1-one 3 were carried out to analyze the features of thienyl group rotation and structural differences with a symmetrical substituent, respectively.
Palabras clave:
Acylcyclohexanediones
,
Tautomerism
,
Rmn
,
Computational Chemistry
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Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Chans, Guillermo Manuel; Moyano, Elizabeth Laura; Baumgartner, Maria Teresa del V.; NMR and computational studies on tautomerism of 3-hydroxy-2-(2-thienylcarbonyl) cyclohex-2-en-1-one; Elsevier Science; Journal of Molecular Structure; 1079; 12-2013; 176-184
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