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

ilustraciones a color, diagramas, tablas

Autores:: Martinez Manjarres, Harold Alejandro

Tipo de recurso:

Fecha de publicación:: 2020

Institución:: Universidad Nacional de Colombia

Repositorio:: Universidad Nacional de Colombia

Idioma:: spa

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dc.title.spa.fl_str_mv	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
dc.title.translated.eng.fl_str_mv	Influence of non-covalent interactions in the course of the reaction between benzidine derivatives, bisphenol A and formaldehyde.
title	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
spellingShingle	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído 540 - Química y ciencias afines Formaldehídos Formaldehyde Hydrogen bridge Puente de hidrógeno Bencidina Formaldehído Bisfenol Reacción de Mannich Puente de hidrógeno N-alcoximetilamina Benzoxazina Condensación Benzidine Formaldehyde Mannich reaction Hydrogen bridge
title_short	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
title_full	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
title_fullStr	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
title_full_unstemmed	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
title_sort	Influencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehído
dc.creator.fl_str_mv	Martinez Manjarres, Harold Alejandro
dc.contributor.advisor.none.fl_str_mv	Quevedo, Rodolfo
dc.contributor.author.none.fl_str_mv	Martinez Manjarres, Harold Alejandro
dc.contributor.researchgroup.spa.fl_str_mv	Química Macrocíclica
dc.subject.ddc.spa.fl_str_mv	540 - Química y ciencias afines
topic	540 - Química y ciencias afines Formaldehídos Formaldehyde Hydrogen bridge Puente de hidrógeno Bencidina Formaldehído Bisfenol Reacción de Mannich Puente de hidrógeno N-alcoximetilamina Benzoxazina Condensación Benzidine Formaldehyde Mannich reaction Hydrogen bridge
dc.subject.other.none.fl_str_mv	Formaldehídos Formaldehyde Hydrogen bridge Puente de hidrógeno
dc.subject.proposal.spa.fl_str_mv	Bencidina Formaldehído Bisfenol Reacción de Mannich Puente de hidrógeno N-alcoximetilamina Benzoxazina Condensación
dc.subject.proposal.eng.fl_str_mv	Benzidine Formaldehyde Mannich reaction Hydrogen bridge
description	ilustraciones a color, diagramas, tablas
publishDate	2020
dc.date.issued.none.fl_str_mv	2020-11-11
dc.date.accessioned.none.fl_str_mv	2021-05-05T18:34:41Z
dc.date.available.none.fl_str_mv	2021-05-05T18:34:41Z
dc.type.spa.fl_str_mv	Trabajo de grado - Maestría
dc.type.driver.spa.fl_str_mv	info:eu-repo/semantics/masterThesis
dc.type.version.spa.fl_str_mv	info:eu-repo/semantics/acceptedVersion
dc.type.content.spa.fl_str_mv	Other
dc.type.redcol.spa.fl_str_mv	http://purl.org/redcol/resource_type/TM
status_str	acceptedVersion
dc.identifier.uri.none.fl_str_mv	https://repositorio.unal.edu.co/handle/unal/79479
dc.identifier.instname.spa.fl_str_mv	Universidad Nacional de Colombia
dc.identifier.reponame.spa.fl_str_mv	Repositorio Institucional Universidad Nacional de Colombia
dc.identifier.repourl.spa.fl_str_mv	https://repositorio.unal.edu.co/
url	https://repositorio.unal.edu.co/handle/unal/79479 https://repositorio.unal.edu.co/
identifier_str_mv	Universidad Nacional de Colombia Repositorio Institucional Universidad Nacional de Colombia
dc.language.iso.spa.fl_str_mv	spa
language	spa
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spelling	Atribución-NoComercial-SinDerivadas 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Quevedo, Rodolfof1eca04d10b58980ca0c01fd730e0f20600Martinez Manjarres, Harold Alejandro085c10ffed68346a5e56ecf112e794ef600Química Macrocíclica2021-05-05T18:34:41Z2021-05-05T18:34:41Z2020-11-11https://repositorio.unal.edu.co/handle/unal/79479Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones a color, diagramas, tablasEstudios 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.Spectroscopic 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.MaestríaSíntesis Orgánica1 recurso en línea (141 páginas)application/pdfspaUniversidad Nacional de ColombiaBogotá - Ciencias - Maestría en Ciencias - QuímicaDepartamento de QuímicaFacultad de CienciasBogotáUniversidad Nacional de Colombia - Sede Bogotá540 - Química y ciencias afinesFormaldehídosFormaldehydeHydrogen bridgePuente de hidrógenoBencidinaFormaldehídoBisfenolReacción de MannichPuente de hidrógenoN-alcoximetilaminaBenzoxazinaCondensaciónBenzidineFormaldehydeMannich reactionHydrogen bridgeInfluencia de interacciones no covalentes en el curso de reacción entre derivados de bencidina, bisfenol A y formaldehídoInfluence of non-covalent interactions in the course of the reaction between benzidine derivatives, bisphenol A and formaldehyde.Trabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionOtherhttp://purl.org/redcol/resource_type/TM[1] Petri M. 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Krueger, “Intramolecular NH⋯O and NH⋯S hydrogen bonds in o-aminophenols and o-aminothiophenols,” Tetrahedron, vol. 26, no. 20, pp. 4753–4764, 1970, doi: 10.1016/S0040-4020(01)93126-6.ORIGINALTesis versión final.pdfTesis versión final.pdfTesis de Maestría en Ciencias - Químicaapplication/pdf4690109https://repositorio.unal.edu.co/bitstream/unal/79479/1/Tesis%20versi%c3%b3n%20final.pdfee5c3915dff3134e4e89365ea13e6bbeMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-83964https://repositorio.unal.edu.co/bitstream/unal/79479/2/license.txtcccfe52f796b7c63423298c2d3365fc6MD52THUMBNAILTesis versión final.pdf.jpgTesis versión final.pdf.jpgGenerated Thumbnailimage/jpeg5281https://repositorio.unal.edu.co/bitstream/unal/79479/3/Tesis%20versi%c3%b3n%20final.pdf.jpg6b38f0ed3875f82871ec73a272a018b8MD53unal/79479oai:repositorio.unal.edu.co:unal/794792024-07-08 23:39:53.864Repositorio Institucional Universidad Nacional de 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