Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído

dc.contributorQuevedo, Rodolfo
dc.contributorQuímica Macrocíclica
dc.creatorMartinez Manjarres, Harold Alejandro
dc.date.accessioned2021-05-05T18:34:41Z
dc.date.available2021-05-05T18:34:41Z
dc.date.created2021-05-05T18:34:41Z
dc.date.issued2020-11-11
dc.identifierhttps://repositorio.unal.edu.co/handle/unal/79479
dc.identifierUniversidad Nacional de Colombia
dc.identifierRepositorio Institucional Universidad Nacional de Colombia
dc.identifierhttps://repositorio.unal.edu.co/
dc.description.abstractEstudios espectroscópicos y computacionales permitieron establecer que bisfenol A y o-dianisidina se asocian por puentes de hidrógeno intermoleculares formando un arreglo cíclico asimétrico. Los efectos geométricos y conformacionales inducidos por este arreglo inciden en el curso de la reacción con formaldehído e impiden la formación de compuestos macrocíclicos y de oligómeros benzoxazinicos. Cuando se hizo reaccionar bisfenol A, o-dianisidina y formaldehído empleando DMF como disolvente, se obtuvo el respectivo monómero benzoxazínico como producto mayoritario. Cuando se utilizó etanol como disolvente, la reacción siguió un curso diferente, el bisfenol A no participó y se obtuvo una N-etoximetilamina producto de la condensación tipo Mannich entre o-dianisidina, formaldehído y etanol. En este trabajo se presenta el análisis estructural de estas nuevas bases de Mannich y se propone una posible explicación para el comportamiento observado basada en la nucleofília de las aminas estudiadas. Finalmente, se estableció que las N-etoximetilaminas son intermediarios de la reacción de Mannich y frente a fenoles se comportan como agentes donores de formaldehído llevando a la formación de benzoxazinas.
dc.description.abstractSpectroscopic and computational studies allowed to establish the association between bisphenol A and o-dianisidine through intermolecular hydrogen bonds, forming an asymmetric cyclic arrangement. The geometric and conformational effects induced by this arrangement affect the reaction course with formaldehyde and prevent the formation of macrocyclic compounds and benzoxazine oligomers. When bisphenol A, o-dianisidine and formaldehyde were reacted using DMF as solvent, the respective benzoxazine monomer was obtained as the major product. When ethanol was used as solvent, the reaction followed a different course, bisphenol A did not participate and N-ethoxymethylamine product was obtained from a Mannich type condensation between o-dianisidine, formaldehyde and ethanol. In this work, the structural analysis of these new Mannich bases is presented and a possible explanation for the observed behavior is proposed based on the nucleophilicity of the studied amines. Finally, it was established that N-ethoxymethylamines are intermediaries of the Mannich reaction and they behave as formaldehyde donor agents with phenols leading to the formation of benzoxazines.
dc.languagespa
dc.publisherUniversidad Nacional de Colombia
dc.publisherBogotá - Ciencias - Maestría en Ciencias - Química
dc.publisherDepartamento de Química
dc.publisherFacultad de Ciencias
dc.publisherBogotá
dc.publisherUniversidad Nacional de Colombia - Sede Bogotá
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dc.rightsAtribución-NoComercial-SinDerivadas 4.0 Internacional
dc.rightshttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rightsinfo:eu-repo/semantics/openAccess
dc.titleInfluencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
dc.typeTrabajo de grado - Maestría


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