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Abstract:

Proton chemical shifts of the following substituted ortho-dimethoxyphenethylamine derivatives: N-2-(2-nitro-4,5-dimethoxyphenyl)ethylphthalimide (1); N-2-(2-nitro-4,5-dimethoxyphenyl)ethylmaleimide (2); 2-nitro-4,5-dimethoxyphenylethylamine (3); N-2-(2-bromo-4,5-dimethoxyphenyl)ethylphthalimide (4); N-2-(2,3-dinitro-4,5-dimethoxy-phenyl)ethylphthalimide (5); 3,4-dimethoxyphenylethylamine (6), N-2-(3,4-dimethoxyphenyl)ethylmaleimide (7), N-2-(3,4-dimethoxyphenyl)ethylphthalimide (8) were determined in the present work. Significant differences between chemical shifts of methoxy groups of N-2-(2-nitro-4,5-dimethoxyphenyl)ethylphthalimide (1) compared to those of the other studied compounds were found. It is attributed to the differential influence of the phthalimide group on the methoxy groups. Methoxy group (2) is closer to the phthalimide group, so it is shielded by the π system, resulting in a significant lower chemical shift than methoxy group (1). Calculated 1H chemical shifts for some of the above molecules showed that lower-energy conformers play a relevant role to achieve good agreement with experimental data. The inclusion of conformers lying about 2 kcal/mol above the lowest-energy conformer for each molecule reduced dramatically absolute errors in chemical shifts, and allowed the assignment and interpretation of experimental data. © 2007 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives
Autor:Vitale, A.A.; Stahl, A.E.; Cecilia dos Santos Claro, P.; Alejandra Floridia Addato, M.; Pis Diez, R.; Jubert, A.H.
Filiación:PROPLAME-PRHIDEB (UBA-CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
CEQUINOR, Centro de Química Inorgánica, CONICET, UNLP, CC 962, B1900AVV La Plata, Argentina
Cátedra de Química Teórica, Departamento de Química, Facultad de Ciencias Exactas, La Plata, Argentina
Palabras clave:Density functional calculations; Maleimide/phthalimide derivatives; Methoxy chemical shifts; Substituted dimethoxyphenethylamines; Chemical shift; Conformations; Density functional theory; Derivatives; Substitution reactions; Methoxy chemical shifts; Methoxy groups; Phthalimide derivatives; Substituted dimethoxyphenethylamines; Functional groups
Año:2008
Volumen:881
Número:1-3
Página de inicio:167
Página de fin:174
DOI: http://dx.doi.org/10.1016/j.molstruc.2007.09.019
Título revista:Journal of Molecular Structure
Título revista abreviado:J. Mol. Struct.
ISSN:00222860
CODEN:JMOSB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v881_n1-3_p167_Vitale

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Citas:

---------- APA ----------
Vitale, A.A., Stahl, A.E., Cecilia dos Santos Claro, P., Alejandra Floridia Addato, M., Pis Diez, R. & Jubert, A.H. (2008) . Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives. Journal of Molecular Structure, 881(1-3), 167-174.
http://dx.doi.org/10.1016/j.molstruc.2007.09.019
---------- CHICAGO ----------
Vitale, A.A., Stahl, A.E., Cecilia dos Santos Claro, P., Alejandra Floridia Addato, M., Pis Diez, R., Jubert, A.H. "Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives" . Journal of Molecular Structure 881, no. 1-3 (2008) : 167-174.
http://dx.doi.org/10.1016/j.molstruc.2007.09.019
---------- MLA ----------
Vitale, A.A., Stahl, A.E., Cecilia dos Santos Claro, P., Alejandra Floridia Addato, M., Pis Diez, R., Jubert, A.H. "Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives" . Journal of Molecular Structure, vol. 881, no. 1-3, 2008, pp. 167-174.
http://dx.doi.org/10.1016/j.molstruc.2007.09.019
---------- VANCOUVER ----------
Vitale, A.A., Stahl, A.E., Cecilia dos Santos Claro, P., Alejandra Floridia Addato, M., Pis Diez, R., Jubert, A.H. Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives. J. Mol. Struct. 2008;881(1-3):167-174.
http://dx.doi.org/10.1016/j.molstruc.2007.09.019