Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico
In this research work, our attention was focused on synthesis, characterization, and study of the molecular interaction of C-alkyl and C-phenyl-pyrogallol[4]arenes with three important biological important organic cations known as neurotransmitters. In this sense, the polyphenolic macrocycles tetra(...
- Autores:
-
Casas Hinestroza, José Luis
- Tipo de recurso:
- Doctoral thesis
- Fecha de publicación:
- 2020
- Institución:
- Universidad Nacional de Colombia
- Repositorio:
- Universidad Nacional de Colombia
- Idioma:
- spa
- OAI Identifier:
- oai:repositorio.unal.edu.co:unal/77999
- Acceso en línea:
- https://repositorio.unal.edu.co/handle/unal/77999
- Palabra clave:
- 540 - Química y ciencias afines
543 - Química analítica
547 - Química orgánica
pirogalol[4]arenos
sistemas huésped-hospedero
funcionalización
interacciones moleculares no covalentes
ensambles supramoleculares
pyrogallol[4]arenes
host-guest systems
functionalization
noncovalent interactions
supramolecular assemblies
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- openAccess
- License
- Atribución-NoComercial-SinDerivadas 4.0 Internacional
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Universidad Nacional de Colombia |
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| dc.title.spa.fl_str_mv |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| title |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| spellingShingle |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico 540 - Química y ciencias afines 543 - Química analítica 547 - Química orgánica pirogalol[4]arenos sistemas huésped-hospedero funcionalización interacciones moleculares no covalentes ensambles supramoleculares pyrogallol[4]arenes host-guest systems functionalization noncovalent interactions supramolecular assemblies |
| title_short |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| title_full |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| title_fullStr |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| title_full_unstemmed |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| title_sort |
Síntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológico |
| dc.creator.fl_str_mv |
Casas Hinestroza, José Luis |
| dc.contributor.advisor.spa.fl_str_mv |
Maldonado Villamil, Mauricio |
| dc.contributor.author.spa.fl_str_mv |
Casas Hinestroza, José Luis |
| dc.contributor.corporatename.spa.fl_str_mv |
Universidad Nacional de Colombia |
| dc.contributor.researchgroup.spa.fl_str_mv |
Aplicaciones Analíticas de Compuesto Orgánicos |
| dc.subject.ddc.spa.fl_str_mv |
540 - Química y ciencias afines 543 - Química analítica 547 - Química orgánica |
| topic |
540 - Química y ciencias afines 543 - Química analítica 547 - Química orgánica pirogalol[4]arenos sistemas huésped-hospedero funcionalización interacciones moleculares no covalentes ensambles supramoleculares pyrogallol[4]arenes host-guest systems functionalization noncovalent interactions supramolecular assemblies |
| dc.subject.proposal.spa.fl_str_mv |
pirogalol[4]arenos sistemas huésped-hospedero funcionalización interacciones moleculares no covalentes ensambles supramoleculares |
| dc.subject.proposal.eng.fl_str_mv |
pyrogallol[4]arenes host-guest systems functionalization noncovalent interactions supramolecular assemblies |
| description |
In this research work, our attention was focused on synthesis, characterization, and study of the molecular interaction of C-alkyl and C-phenyl-pyrogallol[4]arenes with three important biological important organic cations known as neurotransmitters. In this sense, the polyphenolic macrocycles tetra(propyl)-pyrogallol[4]arene, tetra(phenyl)-pyrogallol[4]arene and tetra(4-hidroxyphenyl)-pyrogallol[4]arene were synthesized using butanal, benzaldehyde, and 4-hidroxybenzaldehyde respectively in reaction with pyrogallol in ethanol as solvent in all cases, afterward, the isomers mixture was characterized employing spectroscopic methods (1H-NMR, 13C-RMN, 2D-NMR, and FT-IR) and mass spectrometry(ESI-MS) and, a methodology was developed that allows an efficient separation of each isomer. The three macrocycles were derivatized on the upper rim with acetyl and benzoyl groups employing acetic anhydride and benzoyl chloride achieved a total functionalization of each isomer. Finally, the molecular interaction between the neurotransmitters choline, betaine and carnitine with the macrocycles functionalized and without functionalization in cone and boat conformation was carried out in gas phase and solution. The interaction studies indicated that the macrocycles functionalized form 1:1 complexes host-guest with the three neurotransmitters in the gas phase, while the macrocycles without functionalized, only the tetra(propyl)-pyrogallol[4]arene formed complexes with the neurotransmitters. The noncovalent interactions studies in solution indicated that the cone and boat conformers are affective hosts for the three neurotransmitters and some hosts with potential applications in host-guest systems and supramolecular assemblies. |
| publishDate |
2020 |
| dc.date.accessioned.spa.fl_str_mv |
2020-08-12T17:51:37Z |
| dc.date.available.spa.fl_str_mv |
2020-08-12T17:51:37Z |
| dc.date.issued.spa.fl_str_mv |
2020-07-14 |
| dc.type.spa.fl_str_mv |
Trabajo de grado - Doctorado |
| dc.type.driver.spa.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
| dc.type.version.spa.fl_str_mv |
info:eu-repo/semantics/acceptedVersion |
| dc.type.coar.spa.fl_str_mv |
http://purl.org/coar/resource_type/c_db06 |
| dc.type.content.spa.fl_str_mv |
Text |
| format |
http://purl.org/coar/resource_type/c_db06 |
| status_str |
acceptedVersion |
| dc.identifier.citation.spa.fl_str_mv |
José Luis Casas-Hinestroza |
| dc.identifier.uri.none.fl_str_mv |
https://repositorio.unal.edu.co/handle/unal/77999 |
| identifier_str_mv |
José Luis Casas-Hinestroza |
| url |
https://repositorio.unal.edu.co/handle/unal/77999 |
| dc.language.iso.spa.fl_str_mv |
spa |
| language |
spa |
| dc.relation.references.spa.fl_str_mv |
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J. 2011, 17 (34), 9395–9405. |
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Atribución-NoComercial-SinDerivadas 4.0 InternacionalDerechos reservados - Universidad Nacional de ColombiaAcceso abiertohttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Maldonado Villamil, Mauriciodd02606e-8e95-46f2-be9b-94f54c96697dCasas Hinestroza, José Luise35f09da-4711-48db-96f7-6c2f5c20387dUniversidad Nacional de ColombiaAplicaciones Analíticas de Compuesto Orgánicos2020-08-12T17:51:37Z2020-08-12T17:51:37Z2020-07-14José Luis Casas-Hinestrozahttps://repositorio.unal.edu.co/handle/unal/77999In this research work, our attention was focused on synthesis, characterization, and study of the molecular interaction of C-alkyl and C-phenyl-pyrogallol[4]arenes with three important biological important organic cations known as neurotransmitters. In this sense, the polyphenolic macrocycles tetra(propyl)-pyrogallol[4]arene, tetra(phenyl)-pyrogallol[4]arene and tetra(4-hidroxyphenyl)-pyrogallol[4]arene were synthesized using butanal, benzaldehyde, and 4-hidroxybenzaldehyde respectively in reaction with pyrogallol in ethanol as solvent in all cases, afterward, the isomers mixture was characterized employing spectroscopic methods (1H-NMR, 13C-RMN, 2D-NMR, and FT-IR) and mass spectrometry(ESI-MS) and, a methodology was developed that allows an efficient separation of each isomer. The three macrocycles were derivatized on the upper rim with acetyl and benzoyl groups employing acetic anhydride and benzoyl chloride achieved a total functionalization of each isomer. Finally, the molecular interaction between the neurotransmitters choline, betaine and carnitine with the macrocycles functionalized and without functionalization in cone and boat conformation was carried out in gas phase and solution. The interaction studies indicated that the macrocycles functionalized form 1:1 complexes host-guest with the three neurotransmitters in the gas phase, while the macrocycles without functionalized, only the tetra(propyl)-pyrogallol[4]arene formed complexes with the neurotransmitters. The noncovalent interactions studies in solution indicated that the cone and boat conformers are affective hosts for the three neurotransmitters and some hosts with potential applications in host-guest systems and supramolecular assemblies.En este trabajo de investigación, nuestro interés estuvo centrado en la síntesis, caracterización y estudio de la interacción molecular de C-alquil y C-fenil-pirogalol[4]arenos frente a tres cationes orgánicos de interés biológico conocidos por su acción como neurotransmisores. En este sentido se establecieron las mejores condiciones de reacción para la síntesis de tres polifenoles macrocíclicos tetra(propil)-pirogalol[4]areno, tetra(fenil)-pirogalol[4]areno y tetra(4-hidroxifenil)pirogalol[4]areno a partir de butanal, benzaldehído y p-hidroxi-benzaldehído respectivamente en reacción con pirogalol usando etanol como disolvente. Posteriormente, se determinó y caracterizó completamente por métodos espectroscópicos (RMN-1H, RMN-13C, RMN-2D y FT-IR) y espectrometría de masas(ESI-MS) la identidad de la mezcla de isómeros obtenida en la síntesis de los derivados aromáticos, y además se desarrolló una metodología que permitió la separación eficiente de cada isómero. Los tres macrociclos fueron derivatizados con grupos carboxilo usando anhídrido acético y cloruro de benzoilo logrando su funcionalización total. Finalmente, se evaluó la interacción molecular entre los cationes de interés biológico colina, carnitina y betaína frente a los macrociclos sin funcionalizar y funcionalizados en fase gaseosa y en disolución logrando demostrar que todos los macrociclos derivatizados en el borde superior con los grupos acetil y benzoilo forman complejos en estequiometria 1:1 en fase gaseosa con los tres cationes planteados, mientras que, de los macrociclos sin funcionalizar, solamente el tetra(propil)-pirogalol[4]areno forma complejos estables con los tres cationes usados. De igual manera los estudios en disolución mediante titulaciones por RMN-1H permitió establecer que los confórmeros bote(rccc) y cono(rccc) de los macrociclos sin derivatizar y derivatizados son los mejores hospederos de los neurotransmisores planteados con potencial aplicación en el diseño de sistemas huésped-hospedero y ensambles supramoleculares.SÍNTESIS, CARACTERIZACIÓN DE C-ALQUIL Y C-FENIL-PIROGALOL[4]ARENOS FUNCIONALIZADOS CON GRUPOS CARBOXILO EN EL BORDE SUPERIOR Y EVALUACIÓN DE SU INTERACCIÓN CON CATIONES ORGÁNICOS DE INTERÉS BIOLÓGICOLínea de Investigación: Química Analítica y Síntesis OrgánicaDoctorado200application/pdfspa540 - Química y ciencias afines543 - Química analítica547 - Química orgánicapirogalol[4]arenossistemas huésped-hospederofuncionalizacióninteracciones moleculares no covalentesensambles supramolecularespyrogallol[4]areneshost-guest systemsfunctionalizationnoncovalent interactionssupramolecular assembliesSíntesis, caracterización de c-aquil y c-fenil-pirogalol[4]arenos funcionalizados con grupos carboxilo en el borde superior y evaluación de su interacción con cationes orgánicos de interés biológicoTrabajo de grado - Doctoradoinfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_db06TextBogotá - Ciencias - Doctorado en Ciencias - QuímicaDepartamento de QuímicaUniversidad Nacional de Colombia - Sede BogotáSteed, J. 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