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Efectos del intercambio del contraión y la presencia del flúor en los anillos de fenilo laterales sobre las interacciones supramoleculares en sales cuaternarias de amonio
dc.contributor.advisor | Macias, Mario | |
dc.contributor.advisor | Ríos, Amalia | |
dc.contributor.author | Molina Giraldo, Deysy Andrea | |
dc.date.accessioned | 2022-09-26T14:41:52Z | |
dc.date.available | 2023-05-05 | |
dc.date.available | 2022-09-26T14:41:52Z | |
dc.date.issued | 2022-09-26 | |
dc.identifier.uri | https://repositorio.ucaldas.edu.co/handle/ucaldas/18091 | |
dc.description | Ilustraciones, fotos, gráficas | spa |
dc.description.abstract | spa:El estudio de las interacciones supramoleculares ha tomado cada vez más importancia en el campo de la química, debido al papel que juega en el análisis del auto-ensamble molecular, la catálisis enzimática y el estudio farmacológico de nuevos compuestos. Por un lado, el objetivo de la química supramolecular es estudiar las interacciones entre moléculas mediante uniones no covalentes como el enlace de hidrógeno, las interacciones CH•••π, π•••π, catión•••π, anión•••π, el enlace de halógeno, entre otras. Además, los métodos cristalográficos se han convertido en una técnica importante en varias disciplinas científicas, gracias a la alta resolución y precisión de los equipos disponibles, lo cual soporta los estudios supramoleculares de múltiples compuestos de interés clínico y farmacológico. Las investigaciones previas realizadas por nuestro grupo de investigación sobre una serie de sales cuaternarias de amonio de la forma [X-CH2-N(CH3)2-(CH2)n-CH=C(Ph)2]+I- donde n= 2, 3 y 4; X= H, Cl y I, han permitido establecer a algunas moléculas como posibles candidatas en el tratamiento de la leishmaniasis y la enfermedad de Chagas, así mismo, algunos análogos fluorados se han reportado con una actividad antitumoral promisoria. Adicionalmente, se ha reportado en la literatura un análisis cristalográfico de tres sales N-halometiladas, las cuales presentaban interacciones del tipo: enlaces de hidrógeno (C-H•••I y C-H•••π) e interacciones de halógeno C-I•••I-. Por esta razón y con el fin de avanzar con los estudios supramoleculares desarrollados por el grupo, en esta investigación se realizó una variación estructural al integrar átomos de flúor en la posición para de los anillos aromáticos periféricos y se realizó un intercambio iónico del contraión yoduro (I-) por tetrafluoroborato (BF4-), en total se estudiaron 10 sales cuaternarias de amonio. Las modificaciones estructurales de las sales cuaternarias de amonio sobre la longitud de la cadena, así como la presencia o ausencia de flúor en la posición para de los anillos periféricos, fueron llevadas a cabo previamente. En cuanto al intercambio iónico, que se realizó en este trabajo del anión I- por BF4- se utilizó AgBF4 en metanol y las sales obtenidas se recristalizaron en acetona-agua (2:1), aunque algunos de los cristales crecieron en acetona-isopropanol (2:1). Los datos de difracción de rayos X se midieron a diferentes temperaturas y las estructuras cristalinas se refinaron 17 utilizando el programa SHELXL2016. El material gráfico se preparó utilizando el software Mercury 4.1, para los cálculos estructurales se utilizó el software PLATON y para el análisis de las superficies de Hirshfeld se utilizó CrystalExplorer 17.5. Al analizar el efecto de la presencia de flúor en la posición para en los grupos fenilos de las sales cuaternarias de amonio, se encontró, que al igual que las sales no fluoradas, presentan interacciones no covalentes de tipo enlaces de hidrógeno (C-H•••I- y C-H•••π), además se logró detectar un enlace de hidrógeno de tipo C-H•••F, tanto de los -CH2 de la cadena carbonada como de los -CH de los anillos aromáticos y se evidenció una interacción C-F•••π (dispersión de London). Estos cálculos se hicieron usando el software Platón. Por otro lado, las interacciones o enlaces de halógeno tipo C-I•••I-, a partir de los análisis de las superficies de Hirshfeld, permanecen en igual porcentaje a las presentes en las sales análogas no fluoradas, demostrando de esta manera que al incorporar átomos de flúor a los anillos aromáticos no interfiere en esta última interacción. A partir del análisis comparativo de las sales portadoras del anión yoduro vs anión tetrafluoroborato se determinaron las interacciones supramoleculares inherentes sólo al catión amonio orgánico, además de estudiar qué otras interacciones supramoleculares emergen con la presencia del anión tetrafluoroborato. Así, se evidenciaron dos interacciones en las sales con contraión BF4-, la primera conocida en la literatura como enlace de halógeno de tipo C-I•••F, en donde el aceptor del enlace de halógeno es un flúor perteneciente al BF4- y la segunda conocida como enlace de hidrógeno tipo C-H•••F, tanto de los -CH2 de la cadena carbonada como de los -CH de los anillos aromáticos; las demás interacciones (C-H•••I- y C-H•••π) también se presentan, al igual que en las sales análogas con el anión yoduro, pero en diferentes porcentajes calculados a partir de los análisis de las huellas dactilares bidimensionales. | spa |
dc.description.abstract | eng:The study of supramolecular interactions has become increasingly important in the field of chemistry, due to the role it plays in the analysis of molecular self-assembly, enzymatic catalysis and pharmacological study of new compounds. On the one hand, the aim of supramolecular chemistry is to study interactions between molecules through non-covalent bonds such as hydrogen bonding, CH•••π, π•••π, cation•••π, anion•••π, halogen bonding interactions, among others. In addition, crystallographic methods have become an important technique in several scientific disciplines, thanks to the high resolution and precision of the available equipment, which supports supramolecular studies of multiple compounds of clinical and pharmacological interest. Previous investigations carried out by our research group on a series of quaternary ammonium salts of the form [X-CH2-N(CH3)2-(CH2)n-CH=C(Ph)2]+I- where n= 2, 3 and 4; X= H, Cl and I, have allowed establishing some molecules as possible candidates in the treatment of leishmaniasis and Chagas disease, likewise, some fluorinated analogues have been reported with promising antitumor activity. Additionally, a crystallographic analysis of three N-halomethylated salts has been reported in the literature, which presented interactions of the type: hydrogen bonds (C-H•••I and C-H•••π) and halogen C-I•••I- interactions. For this reason and in order to advance with the supramolecular studies developed by the group, in this research a structural variation was performed by integrating fluorine atoms in the para position of the peripheral aromatic rings and an ionic exchange of the iodide counterion (I-) by tetrafluoroborate (BF4-) was performed, in total 10 quaternary ammonium salts were studied. The structural modifications of the quaternary ammonium salts on the chain length, as well as the presence or absence of fluorine in the para position of the peripheral rings, were previously carried out. As for the ion exchange, which was carried out in this work of the I- anion by BF4- AgBF4 in methanol was used and the salts obtained were recrystallized in acetone-water (2:1), although some of the crystals were grown in acetone-isopropanol (2:1). X-ray diffraction data were measured at different temperatures and crystal structures were refined using the SHELXL2016 program. 15 Graphical material was prepared using Mercury 4.1 software, PLATON software was used for structural calculations and CrystalExplorer 17.5 was used for analysis of Hirshfeld surfaces. When analysing the effect of the presence of fluorine in the para position in the phenyl groups of the quaternary ammonium salts, it was found that, like the non-fluorinated salts, they present non-covalent interactions of the hydrogen bond type (C-H•••I- and C-H•••π), in addition a hydrogen bond of the C-H•••F type was detected, both of the -CH2 of the carbon chain and of the -CH of the aromatic rings and a C-F•••π interaction was evidenced (London dispersion). These calculations were made using Plato software. On the other hand, the C-I•••I- type halogen interactions or bonds, from the analysis of the Hirshfeld surfaces, remain in equal percentage to those present in the analogous non-fluorinated salts, thus demonstrating that incorporating fluorine atoms into the aromatic rings does not interfere with the latter interaction. From the comparative analysis of the salts carrying the iodide anion vs. tetrafluoroborate anion, the supramolecular interactions inherent only to the organic ammonium cation were determined, in addition to studying what other supramolecular interactions emerge with the presence of the tetrafluoroborate anion. Thus, two interactions were evidenced in the salts with BF4- counterion, the first one known in the literature as C-I•••F type halogen bonding, where the acceptor of the halogen bond is a fluorine belonging to BF4- and the second one known as C-H•••F type hydrogen bonding, both of the -CH2 of the carbon chain and of the -CH of the aromatic rings; the other interactions (C-H•••I- and C-H•••π) also occur, as in the analogous salts with the iodide anion, but in different percentages calculated from the analyses of the two-dimensional fingerprints. | eng |
dc.description.tableofcontents | Tabla de contenido / Índice de figuras / Índice de tablas / Summary / Resumen / 1. Introducción / 2. Marco teórico / 2.1 Enlaces covalentes vs interacciones no covalentes / 2.2 Energías estabilizadoras de las interacciones no covalentes / 2.3 Química supramolecular / 2.3.1 Principales interacciones supramoleculares / 2.4 Estructura cristalina, cristales y simetría cristalográfica / 2.5 Generalidades de las sales cuaternarias de amonio / 2.5.1 Estudios con sales cuaternarias de amonio en estado cristalino / 2.5.2 Importancia del flúor en productos farmacéuticos / 2.6 Uso de herramientas para el análisis de las interacciones supramoleculares / 2.6.1 Uso del software Mercury para visualización de estructuras cristalinas / 2.6.2 Uso del software Platón para análisis de estructuras cristalinas / 2.6.3 Uso de las superficies de Hirshfeld en el análisis cuantitativo de interacciones intermoleculares (CrystalExplorer 17.5) / 3.1 Estudios con sales cuaternarias de amonio con potencial actividad biológica / 3.2 Síntesis de las sales cuaternarias de amonio usadas como material de partida en este estudio / 3.3 Estudio de interacciones supramoleculares en sales cuaternarias de amonio N-halometiladas 1a, 1b y 1c / 4. Objetivos / 4.1 Objetivo general / 4.2 Objetivos específicos / 5. Parte experimental / 5.1 Generalidades / 5.2 Síntesis de sales cuaternarias de amonio con tetrafluoroborato (BF4 - ) como contraión / 5.2.1 Síntesis de sales cuaternarias de amonio no fluoradas con tetrafluoroborato (BF4 - ) como contraión (3a, 3b y 3c) / 8 5.3 Metodología para la obtención de monocristales de las sales cuaternarias de amonio 3a, 3b y 3c / 5.3.1 Purificación de las sales cuaternarias de amonio no fluoradas con tetrafluoroborato (BF4 - ) como contraión (3a, 3b y 3c) / 5.4 Difracción de monocristales de rayos X y refinamiento estructural de las 10 sales cuaternarias de amonio / 6. Resultados y discusión / 6.1 Aspectos sintéticos y caracterización química de las sales cuaternarias de amonio / 6.1.1 Sales cuaternarias de amonio estudiadas en esta investigación / 6.1.2 Intercambio del contraión yoduro de las sales cuaternarias de amonio por tetrafluoroborato / 6.1.3 Obtención de monocristales de 3a, 3b y 3c / 6.1.4 Caracterización química de las sales cuaternarias de amonio / 6.2 Análisis estructural y supramolecular de las sales cuaternarias de amonio estudiadas / 6.2.1 Datos cristalográficos para los 10 compuestos estudiados / 6.3.1 Análisis estructural para [C4IpF2] + I - (2a), [C5IpF2] + I - (2b) y [C6IpF2] + I - (2c) / 6.3.2 Análisis supramolecular y de la superficie de Hirshfeld para [C4IpF2] + I - (2a), [C5IpF2] + I - (2b) y [C6IpF2] + I - (2c) / 6.3.3 Comparación de las interacciones supramoleculares de las sales [C4IpF2] + I - (2a), [C5IpF2] + I - (2b) y [C6IpF2] + I - (2c) / 6.4.1 Análisis estructural para [C4I] +BF4 - (3a) y [C5I] +BF4 - (3b) / 6.4.2 Análisis supramolecular y de la superficie de Hirshfeld para [C4I] +BF4 - (3a) y [C5I] +BF4 - (3b) / 6.4.3 Comparación de las interacciones supramoleculares de las sales [C4I] +BF4 - (3a) y [C5I] +BF4 - (3b) / 6.5.1 Análisis estructural para [C4CH3pF2] + I - (4a), [C5CH3pF2] + I - (4b) y [C6CH3pF2] + I - (4c) / 6.5.2 Análisis supramolecular y de la superficie de Hirshfeld para [C4CH3pF2] + I - (4a), [C5CH3pF2] + I - (4b) y [C6CH3pF2] + I - (4c) / 6.5.3 Comparación de las interacciones supramoleculares de las sales [C4CH3pF2] + I - (4a), [C5CH3pF2] + I - (4b) y [C6CH3pF2] + I - (4c) / 6.6.1 Análisis estructural para [C5CH3] + I - (5b) y [C6CH3] + I - (5c) / 6.6.2 Análisis supramolecular y de la superficie de Hirshfeld para [C5CH3] + I - (5b) y [C6CH3] + I - (5c).... 106 6.6.3 Comparación de las interacciones supramoleculares de las sales [C5CH3] + I - (5b) y [C6CH3] + I - (5c)109 6.3 Comparación de las interacciones supramoleculares de las sales cuaternarias de amonio preparadas en este estudio / 7. Conclusiones / 8. Perspectivas / Bibliografía / Anexos / Anexo A. Divulgación científica a partir de los resultados de esta investigación / Anexo B. Espectros de RMN1H, RMN13C y RMN13C DEPT-135 de las sales con contraión BF4 - | spa |
dc.format.mimetype | application/pdf | spa |
dc.language.iso | eng | spa |
dc.language.iso | spa | spa |
dc.title | Efectos del intercambio del contraión y la presencia del flúor en los anillos de fenilo laterales sobre las interacciones supramoleculares en sales cuaternarias de amonio | spa |
dc.type | Trabajo de grado - Maestría | spa |
dc.contributor.researchgroup | Grupo de Química Teórica y Bioinformática - QTB (Categoría B) | spa |
dc.description.degreelevel | Maestría | spa |
dc.identifier.instname | Universidad de Caldas | spa |
dc.identifier.reponame | Repositorio Institucional Universidad de Caldas | spa |
dc.identifier.repourl | https://repositorio.ucaldas.edu.co/ | spa |
dc.publisher.faculty | Facultad de Ciencias Exactas y Naturales | spa |
dc.publisher.place | Manizales | spa |
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dc.rights.accessrights | info:eu-repo/semantics/closedAccess | spa |
dc.rights.accessrights | info:eu-repo/semantics/closedAccess | spa |
dc.rights.accessrights | info:eu-repo/semantics/closedAccess | spa |
dc.rights.accessrights | info:eu-repo/semantics/closedAccess | spa |
dc.subject.proposal | Interacciones supramoleculares | spa |
dc.subject.proposal | sales cuaternarias de amonio | spa |
dc.subject.proposal | Cristalografía | spa |
dc.subject.unesco | Química | |
dc.subject.unesco | Análisis químico | |
dc.type.coar | http://purl.org/coar/resource_type/c_bdcc | spa |
dc.type.content | Text | spa |
dc.type.driver | info:eu-repo/semantics/masterThesis | spa |
dc.type.version | info:eu-repo/semantics/publishedVersion | spa |
oaire.version | http://purl.org/coar/version/c_ab4af688f83e57aa | spa |
oaire.accessrights | http://purl.org/coar/access_right/c_f1cf | spa |
dc.description.degreename | Magister en Química | spa |
dc.publisher.program | Maestría en Química | spa |
dc.description.researchgroup | Química Orgánica | spa |
dc.rights.coar | http://purl.org/coar/access_right/c_14cb | spa |