5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares
Ano de defesa: | 2014 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/21625 |
Resumo: | This work describes the synthesis and halogenation of isoxazoles, and its application as a model for investigating complexities in the self-organization of molecules at the supramolecular level, demonstrating that the design of the crystal originates through the emergence of several intermolecular interactions. 5-aryl-isoxazoles were synthesized without solvent by Grindstone Chemistry method in good yields and low reaction time. Two methodologies (conventional and ultrasound radiation) were used to obtain the series of 5-aryl-4-haloisoxazoles from the halogenation of the precursor with N-halosuccinimides (NCS, NBS and NIS). Ultrasound irradiation was more effective for this synthesis, since the products were obtained in lower reaction times and high yields. For iodination with NIS, trifluoracetic acid as a catalyst was necessary. All synthesized compounds were characterized by 1H and 13C NMR, and mass spectrometry. The compounds obtained as crystals were studied at the molecular and supramolecular structural level. The characterization at the molecular level was performed through geometrical x-ray diffraction data, regions of low and high electronic density (electrostatic potential maps), and regions of the intermolecular contacts by Hirshfeld surface. Characteristic patterns were identified from this first analysis. The supramolecular structure was studied through the generation of clusters of the first coordination sphere, where it was possible to identify each of the Mn molecules that constitute the respective clusters, and determine the molecular coordination number (prevalence of 13 and 14). Subsequently, the dimers formed by the molecules M1 and Mn were characterized by areas and energies of contact in CrystalExplorer® and TOPOS® programs, and Gaussian 09 program package (B97D/cc-pVTZ level DFT), respectively. Good linearity was found in both characterizations, showing a strong dependence on the contact area for the respective interactions between molecules. The analysis of these dimers revealed the presence of polarization effects induced by an intermolecular bond on neighboring molecules, and the presence of dimers that had a greater contribution in the cluster, demonstrating the existence of complementarity and cooperation in the stabilization all of the clusters. The robustness of the molecule...molecule interaction was determined by energy and contact normalized data, demonstrating that weak hydrogen bonds can be considered robust in these compounds. The study concludes with a proposal for the process of self-organization of molecules through the formation of robust dimers. Thus, it was possible to infer based on energy data that π...π interactions attract the molecules at a stage prior to crystallization, namely, in solution, while the influence of other types of interactions may occur later. |
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2021-07-28T16:29:26Z2021-07-28T16:29:26Z2014-08-04http://repositorio.ufsm.br/handle/1/21625This work describes the synthesis and halogenation of isoxazoles, and its application as a model for investigating complexities in the self-organization of molecules at the supramolecular level, demonstrating that the design of the crystal originates through the emergence of several intermolecular interactions. 5-aryl-isoxazoles were synthesized without solvent by Grindstone Chemistry method in good yields and low reaction time. Two methodologies (conventional and ultrasound radiation) were used to obtain the series of 5-aryl-4-haloisoxazoles from the halogenation of the precursor with N-halosuccinimides (NCS, NBS and NIS). Ultrasound irradiation was more effective for this synthesis, since the products were obtained in lower reaction times and high yields. For iodination with NIS, trifluoracetic acid as a catalyst was necessary. All synthesized compounds were characterized by 1H and 13C NMR, and mass spectrometry. The compounds obtained as crystals were studied at the molecular and supramolecular structural level. The characterization at the molecular level was performed through geometrical x-ray diffraction data, regions of low and high electronic density (electrostatic potential maps), and regions of the intermolecular contacts by Hirshfeld surface. Characteristic patterns were identified from this first analysis. The supramolecular structure was studied through the generation of clusters of the first coordination sphere, where it was possible to identify each of the Mn molecules that constitute the respective clusters, and determine the molecular coordination number (prevalence of 13 and 14). Subsequently, the dimers formed by the molecules M1 and Mn were characterized by areas and energies of contact in CrystalExplorer® and TOPOS® programs, and Gaussian 09 program package (B97D/cc-pVTZ level DFT), respectively. Good linearity was found in both characterizations, showing a strong dependence on the contact area for the respective interactions between molecules. The analysis of these dimers revealed the presence of polarization effects induced by an intermolecular bond on neighboring molecules, and the presence of dimers that had a greater contribution in the cluster, demonstrating the existence of complementarity and cooperation in the stabilization all of the clusters. The robustness of the molecule...molecule interaction was determined by energy and contact normalized data, demonstrating that weak hydrogen bonds can be considered robust in these compounds. The study concludes with a proposal for the process of self-organization of molecules through the formation of robust dimers. Thus, it was possible to infer based on energy data that π...π interactions attract the molecules at a stage prior to crystallization, namely, in solution, while the influence of other types of interactions may occur later.Este trabalho trata da síntese e halogenação de isoxazóis, e a aplicação como modelos para estudos da complexidade existente na auto-organização das moléculas em nível supramolecular, demonstrando que o desenho do cristal surge pela emergência da atuação de diversas interações intermoleculares. A síntese de 5-aril-isoxazóis realizada através do método sem solvente Grindstone Chemistry resultou em produtos com bons rendimentos e baixo tempo de reação. Duas metodologias (a convencional e irradiação de ultrassom) foram empregadas na obtenção da série de 5-aril-4-haloisoxazóis a partir da halogenação dos precursores com N-halosuccinimidas (NCS, NBS e NIS). A irradiação de ultrassom demonstrou ser mais eficiente para esta síntese, uma vez que os produtos foram obtidos em baixos tempos de reação e com altos rendimentos. Para a iodação dos compostos com NIS foi necessário utilizar ácido trifluoracético como catalisador nas duas metodologias empregadas. Todos os compostos sintetizados foram caracterizados através de RMN de 1H e 13C, e espectrometria de massas. Os compostos obtidos como cristais foram estudados estruturalmente a nível molecular e supramolecular. Em nível molecular foi realizada a caracterização das estruturas através de dados geométricos obtidos pela difração de Raios-x, regiões de baixa e alta densidade eletrônica informadas pelos mapas de potencial eletrostático, mapeamento da Superfície de Hirshfeld identificando regiões com a possibilidade da existência de determinadas interações intermoleculares. Esta primeira análise revelou um padrão característico existente em determinados grupos de estruturas. O estudo estrutural supramolecular ocorreu através da geração dos clusters da primeira esfera de coordenação, onde foi possível identificar cada uma das Mn moléculas que constituem os respectivos clusters, e determinar o número de coordenação molecular (predominância de 13 e 14). Após, os dímeros formados pelas moléculas M1 e Mn foram caracterizados através de áreas e energias envolvidas no contato M1...Mn determinadas pelos programas CrystalExplorer® e TOPOS® , e pacote de programas Gaussian 09 (teoria DFT B97D/cc-pVTZ), respectivamente. Em ambas as caracterizações uma boa linearidade foi encontrada, demonstrando que existe uma grande dependência da área de contato para as respectivas interações entre as moléculas. A análise conjunta destes dímeros revelou a presença dos efeitos de polarização induzidos por uma ligação intermolecular sobre as moléculas vizinhas, bem como a presença de dímeros que apresentam maior ou menor contribuição no cluster, e com isso foi possível perceber que existe uma cooperatividade e uma complementaridade na estabilização total do cluster de cada estrutura. A determinação da robustez da interação molécula...molécula destas estruturas foi realizada através do comparativo dos dados de energia e contato normalizados, demonstrando que as ligações de hidrogênio fracas C-H ...O e C-H ...N encontradas nestes compostos podem ser consideradas robustas. O estudo realizado encerra-se com a proposta do processo de auto-organização das moléculas a partir da formação de dímeros robustos, onde foi possível inferir, com base em dados energéticos, que interações π...π devem unir as moléculas já no estágio anterior à cristalização, ou seja, em solução, enquanto que posteriormente ocorre a influência dos demais tipos de interações.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessIsoxazolSínteseCálculo teóricoInteração intermolecularIsoxazoleSynthesisTheoretical calculatioIntermolecular interactionCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares5-Aryl-isoxazoles – synthesis and application as model for supramolecular studiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Frizzo, Clarissa PiccininBack, Davi FernandoFantinel, LeonardoDucati, Lucas Coluccihttp://lattes.cnpq.br/7160624661402913Longhi, Kelvis10060000000060092b5c9b6-255c-4e53-af16-c05ebc3898526c5e8995-3451-41f8-92bb-ccc7c7ad4dcdbf4338e5-e87c-4326-93b7-60f8f505f466f33f5bf0-5193-4fac-992b-192381823da8eba5e7a6-11ae-4c8d-8467-992f3d7d46e690a54fd6-e8e9-4b2a-a916-9f6e5b8fa45dreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
dc.title.alternative.eng.fl_str_mv |
5-Aryl-isoxazoles – synthesis and application as model for supramolecular studies |
title |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
spellingShingle |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares Longhi, Kelvis Isoxazol Síntese Cálculo teórico Interação intermolecular Isoxazole Synthesis Theoretical calculatio Intermolecular interaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
title_full |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
title_fullStr |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
title_full_unstemmed |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
title_sort |
5-Aril-isoxazóis – síntese e aplicação como modelos para estudos supramoleculares |
author |
Longhi, Kelvis |
author_facet |
Longhi, Kelvis |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee2.fl_str_mv |
Back, Davi Fernando |
dc.contributor.referee3.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee4.fl_str_mv |
Ducati, Lucas Colucci |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7160624661402913 |
dc.contributor.author.fl_str_mv |
Longhi, Kelvis |
contributor_str_mv |
Martins, Marcos Antonio Pinto Frizzo, Clarissa Piccinin Back, Davi Fernando Fantinel, Leonardo Ducati, Lucas Colucci |
dc.subject.por.fl_str_mv |
Isoxazol Síntese Cálculo teórico Interação intermolecular |
topic |
Isoxazol Síntese Cálculo teórico Interação intermolecular Isoxazole Synthesis Theoretical calculatio Intermolecular interaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Isoxazole Synthesis Theoretical calculatio Intermolecular interaction |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis and halogenation of isoxazoles, and its application as a model for investigating complexities in the self-organization of molecules at the supramolecular level, demonstrating that the design of the crystal originates through the emergence of several intermolecular interactions. 5-aryl-isoxazoles were synthesized without solvent by Grindstone Chemistry method in good yields and low reaction time. Two methodologies (conventional and ultrasound radiation) were used to obtain the series of 5-aryl-4-haloisoxazoles from the halogenation of the precursor with N-halosuccinimides (NCS, NBS and NIS). Ultrasound irradiation was more effective for this synthesis, since the products were obtained in lower reaction times and high yields. For iodination with NIS, trifluoracetic acid as a catalyst was necessary. All synthesized compounds were characterized by 1H and 13C NMR, and mass spectrometry. The compounds obtained as crystals were studied at the molecular and supramolecular structural level. The characterization at the molecular level was performed through geometrical x-ray diffraction data, regions of low and high electronic density (electrostatic potential maps), and regions of the intermolecular contacts by Hirshfeld surface. Characteristic patterns were identified from this first analysis. The supramolecular structure was studied through the generation of clusters of the first coordination sphere, where it was possible to identify each of the Mn molecules that constitute the respective clusters, and determine the molecular coordination number (prevalence of 13 and 14). Subsequently, the dimers formed by the molecules M1 and Mn were characterized by areas and energies of contact in CrystalExplorer® and TOPOS® programs, and Gaussian 09 program package (B97D/cc-pVTZ level DFT), respectively. Good linearity was found in both characterizations, showing a strong dependence on the contact area for the respective interactions between molecules. The analysis of these dimers revealed the presence of polarization effects induced by an intermolecular bond on neighboring molecules, and the presence of dimers that had a greater contribution in the cluster, demonstrating the existence of complementarity and cooperation in the stabilization all of the clusters. The robustness of the molecule...molecule interaction was determined by energy and contact normalized data, demonstrating that weak hydrogen bonds can be considered robust in these compounds. The study concludes with a proposal for the process of self-organization of molecules through the formation of robust dimers. Thus, it was possible to infer based on energy data that π...π interactions attract the molecules at a stage prior to crystallization, namely, in solution, while the influence of other types of interactions may occur later. |
publishDate |
2014 |
dc.date.issued.fl_str_mv |
2014-08-04 |
dc.date.accessioned.fl_str_mv |
2021-07-28T16:29:26Z |
dc.date.available.fl_str_mv |
2021-07-28T16:29:26Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/21625 |
url |
http://repositorio.ufsm.br/handle/1/21625 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
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atendimento.sib@ufsm.br||tedebc@gmail.com |
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