Hindered Rotation in N-Carbomethoxylated Indole Derivatives
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| Format: | Artículo científico |
| Sprache: | en |
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Sociedad Química de México
2001
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| _version_ | 1876436807267123200 |
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| author | Martha S. Morales Ríos |
| author_facet | Martha S. Morales Ríos |
| contents | Hindered Rotation in N-Carbomethoxylated Indole Derivatives Martha S. Morales Ríos Norma F. Santos Sánchez Pedro Joseph Nathan Multidisciplinaria (Ciencias Naturales y Exactas) NMR hindered rotation dynamic processes carbomethoxyindoles N-Carbomethoxyindole derivatives display 1H NMRdynamic processes arising from the hindered rotation about the N-Ccarbamate bond. Theoretical modeling by Molecular Mechanics predictstwo conformational minima A and B, owing to the E and Z isomersof the carbamate group. Conformer A, with the carbonyl carbamategroup oriented towards the benzene ring is, in most cases, morestable than the B conformer. A hydrogen bond provides an explanationfor the preference of the B conformer in 2. The energy profilesreveal that, between the molecules investigated, compound 3 has thelowest barrier to rotation for the interconversion of the A and B conformers.The relative energies of 3 favored the A conformer in largeproportion (97:3). These results are consistent with the observedsharp signals in the 1H NMR spectrum of 3, while compounds 2, 6and 7 show some significantly broadened signals in their 1H and 13CNMR spectra. 2001 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47545408 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.45 |
| format | Artículo científico |
| id | redalyc_47545408 |
| institution | Redalyc |
| language | en |
| publishDate | 2001 |
| publisher | Sociedad Química de México |
| spellingShingle | Hindered Rotation in N-Carbomethoxylated Indole Derivatives Martha S. Morales Ríos Multidisciplinaria (Ciencias Naturales y Exactas) NMR hindered rotation dynamic processes carbomethoxyindoles Hindered Rotation in N-Carbomethoxylated Indole Derivatives Martha S. Morales Ríos Norma F. Santos Sánchez Pedro Joseph Nathan Multidisciplinaria (Ciencias Naturales y Exactas) NMR hindered rotation dynamic processes carbomethoxyindoles N-Carbomethoxyindole derivatives display 1H NMRdynamic processes arising from the hindered rotation about the N-Ccarbamate bond. Theoretical modeling by Molecular Mechanics predictstwo conformational minima A and B, owing to the E and Z isomersof the carbamate group. Conformer A, with the carbonyl carbamategroup oriented towards the benzene ring is, in most cases, morestable than the B conformer. A hydrogen bond provides an explanationfor the preference of the B conformer in 2. The energy profilesreveal that, between the molecules investigated, compound 3 has thelowest barrier to rotation for the interconversion of the A and B conformers.The relative energies of 3 favored the A conformer in largeproportion (97:3). These results are consistent with the observedsharp signals in the 1H NMR spectrum of 3, while compounds 2, 6and 7 show some significantly broadened signals in their 1H and 13CNMR spectra. 2001 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47545408 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.45 |
| title | Hindered Rotation in N-Carbomethoxylated Indole Derivatives |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) NMR hindered rotation dynamic processes carbomethoxyindoles |
| url | https://www.redalyc.org/articulo.oa?id=47545408 |