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Título : Estudio teórico-experimental de la síntesis y propiedades físico-químicas de derivados de N-bencil-1-(2-furanil) Metanamina
Autor : Corredor Montaña, Jeisson David
Director de Trabajo de Grado: Gómez Castaño, Jovanny Arlés (Director de tesis)
Palabras clave: Reacción de Diels-Alder
Síntesis orgánica
Cicloadición
Maestría en Química - Tesis y disertaciones académicas
Fecha de publicación : 2018
Editorial : Universidad Pedagógica y Tecnológica de Colombia
Citación : Corredor Montaña, J. D. (2018). Estudio teórico-experimental de la síntesis y propiedades físico-químicas de derivados de N-bencil-1-(2-furanil) Metanamina. (Tesis de maestría). Universidad Pedagógica y Tecnológica de Colombia, Tunja. http://repositorio.uptc.edu.co/handle/001/2506
Resumen : Se desarrolló el estudio teórico-experimental del sistema de reacción y los productos de cicloadición DA de N-bencil-1-(2-furanil)metanamina (1a), y N-bencil-N-(2-furanilmetilen)acetamida (1b); empleando como dienófilo anhídrido maléico (AnM). La síntesis se llevó a cabo modificando las metodologías experimentales en el marco de la química verde. La caracterización espectroscópica de todas las moléculas se realizó mediante espectroscopia de RMN mono y bidimensional, FTIR, FTRaman, Espectrometría de masas y cálculos computacionales vibracionales al nivel B3LYP/6-31G+(d). El aducto de cicloadición de la amina 1a se obtuvo como una mezcla racémica del isómero exo con estructura cristalina monoclínica. Las moléculas se acomodan formando dímeros centro-simétricos enlazados por puentes de hidrógeno. El estudio computacional preeliminar al nivel B3LYP/6-31G+(d) de estructuras de transición propuestas para éste sistema, permitió identificar algunos factores que pueden determinar el mecanismo de reacción. Las dos rutas evaluadas presentan factores que pueden conducir a la selectividad exo del aducto. Las evidencias experimentales de RMN y FTIR requieren análisis complementarios para dar claridad respecto al intermediario detectado. La amida 1b obtenida por acetilación de la amina 1a, se obtuvo como una mezcla de isómeros E-Z y confórmeros que presenta diferenciación de ambientes en RMN. Su cicloadición DA produjo el isómero Z-exo del aducto, que presenta cicloreversibilidad en solución a temperatura ambiente, regenerando la mezcla isomérica E-Z. También, se reportó la síntesis de las sales orgánicas maleato y acetato de la amina 1a.
Descripción : 1 recurso en línea (100 páginas) : figuras, tablas.
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