Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy
The structural and vibrational properties of caffeic acid phenethyl ester (CAPE) were studied using infrared and Raman spectroscopy in the solid phase and multidimensional nuclear magnetic resonance (NMR) spectroscopy in solution. The theoretical structures of the compound and of its dimer in the ga...
| Autores principales: | , , , , , , |
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| Formato: | Artículo |
| Lenguaje: | Inglés |
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2018
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| Acceso en línea: | https://www.sciencedirect.com/science/article/pii/S0924203113001513 http://hdl.handle.net/20.500.12123/3274 https://doi.org/10.1016/j.vibspec.2013.11.008 |
| _version_ | 1855483211519361024 |
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| author | Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia |
| author_browse | Brandan, Silvia Antonia Castillo, María Victoria Leyton, Patricio Maldonado, Luis Maria Paipa, Carolina Raschi, Ana Beatriz Romano, Elida |
| author_facet | Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia |
| author_sort | Raschi, Ana Beatriz |
| collection | INTA Digital |
| description | The structural and vibrational properties of caffeic acid phenethyl ester (CAPE) were studied using infrared and Raman spectroscopy in the solid phase and multidimensional nuclear magnetic resonance (NMR) spectroscopy in solution. The theoretical structures of the compound and of its dimer in the gas phase and in DMSO solution by using density functional theory (DFT) were studied. The harmonic vibrational frequencies for the optimized geometry of CAPE and its dimeric species were calculated at the B3LYP level of theory using the 6–31G* basis set. These data allow a complete assignment of the vibration modes of the FTIR and Raman spectra in the solid state using the scaled quantum mechanical force field (SQMFF) methodology. The vibrational analysis for the dimer was performed taking into account the correlation diagram by means of the factor group analysis in accordance with the experimental structure determined by X-ray diffraction. The presence of the dimer of CAPE is supported by the IR bands at 1654, 1635, 1563, 1533, 1300, 1107, 1050, 738 cm−1 and the Raman bands at 1684, 1681, 1634, 1112, 1050, 928, 873, 850, 740, 445, 371 and 141 cm−1. The calculated 1H and 13C chemicals shifts are consistent with the corresponding experimental NMR spectra of the compound in solution. In addition, a natural bond orbital (NBO) study revealed the characteristics of the electronic delocalization of the stable structure, while the corresponding topological properties of the electronic charge density were analyzed by employing Bader's atoms in the molecules theory (AIM). |
| format | Artículo |
| id | INTA3274 |
| institution | Instituto Nacional de Tecnología Agropecuaria (INTA -Argentina) |
| language | Inglés |
| publishDate | 2018 |
| publishDateRange | 2018 |
| publishDateSort | 2018 |
| record_format | dspace |
| spelling | INTA32742018-09-03T13:34:17Z Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear The structural and vibrational properties of caffeic acid phenethyl ester (CAPE) were studied using infrared and Raman spectroscopy in the solid phase and multidimensional nuclear magnetic resonance (NMR) spectroscopy in solution. The theoretical structures of the compound and of its dimer in the gas phase and in DMSO solution by using density functional theory (DFT) were studied. The harmonic vibrational frequencies for the optimized geometry of CAPE and its dimeric species were calculated at the B3LYP level of theory using the 6–31G* basis set. These data allow a complete assignment of the vibration modes of the FTIR and Raman spectra in the solid state using the scaled quantum mechanical force field (SQMFF) methodology. The vibrational analysis for the dimer was performed taking into account the correlation diagram by means of the factor group analysis in accordance with the experimental structure determined by X-ray diffraction. The presence of the dimer of CAPE is supported by the IR bands at 1654, 1635, 1563, 1533, 1300, 1107, 1050, 738 cm−1 and the Raman bands at 1684, 1681, 1634, 1112, 1050, 928, 873, 850, 740, 445, 371 and 141 cm−1. The calculated 1H and 13C chemicals shifts are consistent with the corresponding experimental NMR spectra of the compound in solution. In addition, a natural bond orbital (NBO) study revealed the characteristics of the electronic delocalization of the stable structure, while the corresponding topological properties of the electronic charge density were analyzed by employing Bader's atoms in the molecules theory (AIM). EEA Famaillá Fil: Raschi, Ana Beatriz. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; Argentina Fil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; Argentina Fil: Castillo, María Victoria. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; Argentina Fil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso. Instituto de Química; Chile Fil: Paipa, Carolina. Universidad de Playa Ancha. Facultad de Ciencias Naturales y Exactas. Departamento Disciplinario de Química; Chile Fil: Maldonado, Luis Maria. Instituto Nacional de Tecnología Agropecuaria (INTA). Estación Experimental Agropecuaria Famaillá; Argentina Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; Argentina 2018-09-03T13:32:09Z 2018-09-03T13:32:09Z 2014-01 info:ar-repo/semantics/artículo info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion https://www.sciencedirect.com/science/article/pii/S0924203113001513 http://hdl.handle.net/20.500.12123/3274 0924-2031 https://doi.org/10.1016/j.vibspec.2013.11.008 eng info:eu-repo/semantics/restrictedAccess application/pdf Vibrational Spectroscopy 70 : 100-109 (January 2014) |
| spellingShingle | Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title | Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title_full | Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title_fullStr | Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title_full_unstemmed | Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title_short | Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| title_sort | vibrational study of caffeic acid phenethyl ester a potential anticancer agent by infrared raman and nmr spectroscopy |
| topic | Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear |
| url | https://www.sciencedirect.com/science/article/pii/S0924203113001513 http://hdl.handle.net/20.500.12123/3274 https://doi.org/10.1016/j.vibspec.2013.11.008 |
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