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Abstract:

The proton‐coupled 13C NMR spectra of 1‐trans‐methoxy‐ (2) and 1‐cis‐methoxy‐1,3‐trans‐butadiene (3) are consistent with a methoxy heavy atom planar conformation with s‐syn and s‐anti orientations, respectively. Ab initio 6–31G* calculations confirmed such conformations. They were taken as model compounds to determine the influence of electrostatic interactions on the methoxy 13C NMR parameters. A shielding increase of 4 ppm is observed in 2, with respect to 3, for the OMe 13C chemical shift in an s‐syn conformation and is ascribed to the attraction between the methyl and vinyl moieties as proposed by Li and Chesnut. The methyl 1J(C,H) coupling is not affected by this interaction, showing that the carbon 2p electrons are more polarizable than those in the 2s orbital. Copyright © 1994 John Wiley & Sons Limited

Registro:

Documento: Artículo
Título:Methoxy group conformation effects on 13C NMR parameters in 1‐cis‐methoxy‐ and 1‐trans‐methoxy‐1,3‐trans‐butadiene
Autor:Esteban, A.L.; Galache, M.P.; Diez, E.; Biekofsky, R.R.; Contreras, R.H.
Filiación:Departamento de Química-Física, Universidad de Alicante, Alicante, 03080, Spain
Facultad de Ciencias C2-103, Universidad Autónoma de Madrid, Madrid, 28049, Spain
Departamento de Física, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón I, Buenos Aires, 1428, Argentina
Palabras clave:13C NMR; 1‐cis‐Methoxy‐1,3‐trans‐butadiene; 1‐trans‐Methoxy‐1,3‐trans‐butadiene; Ab initio calculations; Conformation; NMR
Año:1994
Volumen:32
Número:4
Página de inicio:199
Página de fin:204
DOI: http://dx.doi.org/10.1002/mrc.1260320402
Título revista:Magnetic Resonance in Chemistry
Título revista abreviado:Magn. Reson. Chem.
ISSN:07491581
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v32_n4_p199_Esteban

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Citas:

---------- APA ----------
Esteban, A.L., Galache, M.P., Diez, E., Biekofsky, R.R. & Contreras, R.H. (1994) . Methoxy group conformation effects on 13C NMR parameters in 1‐cis‐methoxy‐ and 1‐trans‐methoxy‐1,3‐trans‐butadiene. Magnetic Resonance in Chemistry, 32(4), 199-204.
http://dx.doi.org/10.1002/mrc.1260320402
---------- CHICAGO ----------
Esteban, A.L., Galache, M.P., Diez, E., Biekofsky, R.R., Contreras, R.H. "Methoxy group conformation effects on 13C NMR parameters in 1‐cis‐methoxy‐ and 1‐trans‐methoxy‐1,3‐trans‐butadiene" . Magnetic Resonance in Chemistry 32, no. 4 (1994) : 199-204.
http://dx.doi.org/10.1002/mrc.1260320402
---------- MLA ----------
Esteban, A.L., Galache, M.P., Diez, E., Biekofsky, R.R., Contreras, R.H. "Methoxy group conformation effects on 13C NMR parameters in 1‐cis‐methoxy‐ and 1‐trans‐methoxy‐1,3‐trans‐butadiene" . Magnetic Resonance in Chemistry, vol. 32, no. 4, 1994, pp. 199-204.
http://dx.doi.org/10.1002/mrc.1260320402
---------- VANCOUVER ----------
Esteban, A.L., Galache, M.P., Diez, E., Biekofsky, R.R., Contreras, R.H. Methoxy group conformation effects on 13C NMR parameters in 1‐cis‐methoxy‐ and 1‐trans‐methoxy‐1,3‐trans‐butadiene. Magn. Reson. Chem. 1994;32(4):199-204.
http://dx.doi.org/10.1002/mrc.1260320402