Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy
- Autores
- Raschi, Ana Beatriz; Romano, Elida; Castillo, María Victoria; Leyton, Patricio; Paipa, Carolina; Maldonado, Luis Maria; Brandan, Silvia Antonia
- Año de publicación
- 2014
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- 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 - Fuente
- Vibrational Spectroscopy 70 : 100-109 (January 2014)
- Materia
-
Ácido Caféico
Esteres
Vibraciones
Espectroscopia
Espectroscopia RMN
Caffeic Acid
Esters
Vibration
Spectroscopy
NMR Spectroscopy
Estructura Molecular
Espectroscopia Resonancia Magnética Nuclear - Nivel de accesibilidad
- acceso restringido
- Condiciones de uso
- Repositorio
.jpg)
- Institución
- Instituto Nacional de Tecnología Agropecuaria
- OAI Identificador
- oai:localhost:20.500.12123/3274
Ver los metadatos del registro completo
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Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopyRaschi, Ana BeatrizRomano, ElidaCastillo, María VictoriaLeyton, PatricioPaipa, CarolinaMaldonado, Luis MariaBrandan, Silvia AntoniaÁcido CaféicoEsteresVibracionesEspectroscopiaEspectroscopia RMNCaffeic AcidEstersVibrationSpectroscopyNMR SpectroscopyEstructura MolecularEspectroscopia Resonancia Magnética NuclearThe 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 FamailláFil: Raschi, Ana Beatriz. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; ArgentinaFil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; ArgentinaFil: Castillo, María Victoria. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; ArgentinaFil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso. Instituto de Química; ChileFil: Paipa, Carolina. Universidad de Playa Ancha. Facultad de Ciencias Naturales y Exactas. Departamento Disciplinario de Química; ChileFil: Maldonado, Luis Maria. Instituto Nacional de Tecnología Agropecuaria (INTA). Estación Experimental Agropecuaria Famaillá; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Inorganica. Cátedra de Química General; Argentina2018-09-03T13:32:09Z2018-09-03T13:32:09Z2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttps://www.sciencedirect.com/science/article/pii/S0924203113001513http://hdl.handle.net/20.500.12123/32740924-2031https://doi.org/10.1016/j.vibspec.2013.11.008Vibrational Spectroscopy 70 : 100-109 (January 2014)reponame:INTA Digital (INTA)instname:Instituto Nacional de Tecnología Agropecuariaenginfo:eu-repo/semantics/restrictedAccess2025-10-16T09:29:17Zoai:localhost:20.500.12123/3274instacron:INTAInstitucionalhttp://repositorio.inta.gob.ar/Organismo científico-tecnológicoNo correspondehttp://repositorio.inta.gob.ar/oai/requesttripaldi.nicolas@inta.gob.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:l2025-10-16 09:29:18.15INTA Digital (INTA) - Instituto Nacional de Tecnología Agropecuariafalse |
| dc.title.none.fl_str_mv |
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 |
| spellingShingle |
Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy Raschi, Ana Beatriz Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear |
| title_short |
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_sort |
Vibrational study of caffeic acid phenethyl ester, a potential anticancer agent, by infrared, Raman, and NMR spectroscopy |
| dc.creator.none.fl_str_mv |
Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia |
| author |
Raschi, Ana Beatriz |
| author_facet |
Raschi, Ana Beatriz Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia |
| author_role |
author |
| author2 |
Romano, Elida Castillo, María Victoria Leyton, Patricio Paipa, Carolina Maldonado, Luis Maria Brandan, Silvia Antonia |
| author2_role |
author author author author author author |
| dc.subject.none.fl_str_mv |
Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear |
| topic |
Ácido Caféico Esteres Vibraciones Espectroscopia Espectroscopia RMN Caffeic Acid Esters Vibration Spectroscopy NMR Spectroscopy Estructura Molecular Espectroscopia Resonancia Magnética Nuclear |
| dc.description.none.fl_txt_mv |
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 |
| 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). |
| publishDate |
2014 |
| dc.date.none.fl_str_mv |
2014-01 2018-09-03T13:32:09Z 2018-09-03T13:32:09Z |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.none.fl_str_mv |
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 |
| 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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0924-2031 |
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eng |
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eng |
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restrictedAccess |
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application/pdf |
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