Artículo
Molecular structure, experimental and theoretical 1H and 13C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters
Buceta, Norma Nelida; Ruiz, Diego Manuel
; Romanelli, Gustavo Pablo
; Autino, Juan Carlos; Duddeck, Helmunt; Pis Diez, Reinaldo
; Jios, Jorge Luis
Fecha de publicación:
01/2014
Editorial:
John Wiley & Sons Ltd
Revista:
Journal Of Physical Organic Chemistry
ISSN:
0894-3230
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The experimental 1H and 13C NMR spectra of 13 phenyl cinnamates and four 4-methylcoumarins were investigated and their chemical shifts assigned on the basis of the two-dimensional spectra. For the unsubstituted cinnamic acid phenyl ester, optimized molecular structures were calculated at a B3LYP/6-311++G(d,p) level of theory. 1H and 13C NMR chemical shifts were also calculated with the GIAO method at the B3LYP/6-311 + G(2d,p) level of theory. The comparison between experimental and calculated NMR chemical shift suggests that the experimental spectra are formed from the superposition spectra of the two lowest energy conformers of the compound in solution. The most stable s-cis configuration found in our studies is also the conformation adopted for a related phenyl cinnamate in solid state. The experimental results were analyzed in terms of the substituent effects.
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Articulos(CEQUINOR)
Articulos de CENTRO DE QUIMICA INORGANICA "DR. PEDRO J. AYMONINO"
Articulos de CENTRO DE QUIMICA INORGANICA "DR. PEDRO J. AYMONINO"
Articulos(CINDECA)
Articulos de CENTRO DE INV EN CS.APLICADAS "DR.JORGE J.RONCO"
Articulos de CENTRO DE INV EN CS.APLICADAS "DR.JORGE J.RONCO"
Citación
Jios, Jorge Luis; Duddeck, Helmunt; Buceta, Norma Nelida; Autino, Juan Carlos; Ruiz, Diego Manuel; Romanelli, Gustavo Pablo; et al.; Molecular structure, experimental and theoretical 1H and 13C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 27; 2; 1-2014; 106-113
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