Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives
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);...
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2008
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| LEADER | 07846caa a22008657a 4500 | ||
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| 001 | PAPER-5873 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203533.0 | ||
| 008 | 190411s2008 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-43649105438 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMOSB | ||
| 100 | 1 | |a Vitale, A.A. | |
| 245 | 1 | 0 | |a Experimental and theoretical study of the proton methoxy chemical shifts of substituted 3,4-dimethoxyphenethylamines and maleimide/phthalimide derivatives |
| 260 | |c 2008 | ||
| 270 | 1 | 0 | |m Vitale, A.A.; PROPLAME-PRHIDEB (UBA-CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina; email: aavitale@sinectis.com.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 520 | 3 | |a 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. |l eng | |
| 593 | |a PROPLAME-PRHIDEB (UBA-CONICET), Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina | ||
| 593 | |a CEQUINOR, Centro de Química Inorgánica, CONICET, UNLP, CC 962, B1900AVV La Plata, Argentina | ||
| 593 | |a Cátedra de Química Teórica, Departamento de Química, Facultad de Ciencias Exactas, La Plata, Argentina | ||
| 690 | 1 | 0 | |a DENSITY FUNCTIONAL CALCULATIONS |
| 690 | 1 | 0 | |a MALEIMIDE/PHTHALIMIDE DERIVATIVES |
| 690 | 1 | 0 | |a METHOXY CHEMICAL SHIFTS |
| 690 | 1 | 0 | |a SUBSTITUTED DIMETHOXYPHENETHYLAMINES |
| 690 | 1 | 0 | |a CHEMICAL SHIFT |
| 690 | 1 | 0 | |a CONFORMATIONS |
| 690 | 1 | 0 | |a DENSITY FUNCTIONAL THEORY |
| 690 | 1 | 0 | |a DERIVATIVES |
| 690 | 1 | 0 | |a SUBSTITUTION REACTIONS |
| 690 | 1 | 0 | |a METHOXY CHEMICAL SHIFTS |
| 690 | 1 | 0 | |a METHOXY GROUPS |
| 690 | 1 | 0 | |a PHTHALIMIDE DERIVATIVES |
| 690 | 1 | 0 | |a SUBSTITUTED DIMETHOXYPHENETHYLAMINES |
| 690 | 1 | 0 | |a FUNCTIONAL GROUPS |
| 700 | 1 | |a Stahl, A.E. | |
| 700 | 1 | |a Cecilia dos Santos Claro, P. | |
| 700 | 1 | |a Alejandra Floridia Addato, M. | |
| 700 | 1 | |a Pis Diez, R. | |
| 700 | 1 | |a Jubert, A.H. | |
| 773 | 0 | |d 2008 |g v. 881 |h pp. 167-174 |k n. 1-3 |p J. Mol. Struct. |x 00222860 |w (AR-BaUEN)CENRE-222 |t Journal of Molecular Structure | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.molstruc.2007.09.019 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222860_v881_n1-3_p167_Vitale |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v881_n1-3_p167_Vitale |y Registro en la Biblioteca Digital |
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