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dc.contributor.advisorMaldonado Villamil, Mauricio
dc.creatorCasas Hinestroza, José Luis
dc.date.accessioned2020-08-12T17:51:37Z
dc.date.available2020-08-12T17:51:37Z
dc.date.created2020-07-14
dc.identifier.citationJosé Luis Casas-Hinestroza
dc.identifier.urihttps://repositorio.unal.edu.co/handle/unal/77999
dc.descriptionEn 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.
dc.description.abstractIn 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.
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dc.format.mimetypeapplication/pdf
dc.language.isospa
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/2.5/co/
dc.subjectpirogalol[4]arenos
dc.subjectsistemas huésped-hospedero
dc.subjectfuncionalización
dc.subjectinteracciones moleculares no covalentes
dc.subjectensambles supramoleculares
dc.subject.ddc540 - Química y ciencias afines
dc.subject.ddc543 - Química analítica
dc.subject.ddc547 - Química orgánica
dc.titleSíntesis, 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.typeOther
dc.rights.spaAcceso abierto
dc.contributor.institutionUniversidad Nacional de Colombia - Sede Bogotá
dc.subject.keywordpyrogallol[4]arenes
dc.subject.keywordhost-guest systems
dc.subject.keywordfunctionalization
dc.subject.keywordnoncovalent interactions
dc.subject.keywordsupramolecular assemblies
dc.type.spaOtro
dc.type.hasversionAccepted Version
dc.coverage.programDepartamento de Química
dc.contributor.gruplacAplicaciones Analíticas de Compuesto Orgánicos
dc.description.projectSÍNTESIS, 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 BIOLÓGICO
dc.description.additionalLínea de Investigación: Química Analítica y Síntesis Orgánica
dc.coverage.modalityDoctorado
dc.rights.accessRightsOpen Access
dc.rights.ccAtribución-NoComercial-SinDerivadas 2.5 Colombia
dc.contributor.corpauthorUniversidad Nacional de Colombia
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