Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos
Ano de defesa: | 2018 |
---|---|
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/1/14096 |
Resumo: | This study presents the influence of the molecular structure of dicationic ionic liquids (ILs) derived from imidazolium ring, on physicochemical properties, self-association and heteroassociation. Changes in solubility properties, diffusion coefficient, relaxation time and decomposition kinetics were evaluated as a function of the anion structure, for the ILs of 1,8-bis (3-methylimidazol-1-yl) octane cation ([BisOct(MIM)2]2+). The results showed that the partition constant decreases according to the anion in the following order: [BF4]- > [SCN]- > [NO3]- > [Br]- > [Cl]-. Thermal stability is also associated with the anion, in which [BisOct(MIM)2][2NO3] is the most stable IL. On the other hand, the diffusion coefficient data did not vary according to the anion under the conditions tested. The kinetics of the decomposition of dicationic ILs ([BisAlq(MIM)2][2Br]) with different alkyl chain length (10, 12 and 14 carbons) was also evaluated and compared with monocationic analogues. It has been found that the stability is not related with the number of carbons in the structure and that the dicationic IL are more stable than monocationic analogs. The organization and morphology of aggregates of dicationic ILs [BisOct(MIM)2][2X], in which X = Br, NO3, BF4 and SCN, were investigated. It has been observed that the cation alkyl spacer chain is folded, forming spherical aggregates and, that interactions occurring on the aggregate’s surface are dependent on the anions type. Thermodynamic parameters of the aggregation process (ΔG°a, ΔH°a and TΔS°a) determined for [BisOct(MIM)2][2Br] showed that the process is enthalpy driven. In addition, it has been observed that as the temperature increases, the free energy of aggregation (ΔG°a) decreases and the free energy of adsorption increases (ΔG°ads) indicating that the aggregation hability decreases and the IL adsorption at the liquid/air interface increases. In the study of heteroassociation, it was investigated heteroassociation of dicationic ILs with different active pharmaceutical ingredients (APIs): salicylic acid (AS), ibuprofen (Ibu) and Paracetamol (Par). It was observed that ILs and IFAs interact at low concentrations (~2 mM) in ethanol-water solution (1:1, v/v). At high concentrations (~50 mM), the APIs were found to interact probably at aggregates surface of the ILs. Interactions between ILs and APIs have also been proven with both components in the solid state. The supramolecular structure of the system [BisOct(MIM)2][2Br] + AS was obtained by monocrystal X-ray diffraction. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2018-08-24T19:25:08Z2018-08-24T19:25:08Z2018-01-26http://repositorio.ufsm.br/handle/1/14096This study presents the influence of the molecular structure of dicationic ionic liquids (ILs) derived from imidazolium ring, on physicochemical properties, self-association and heteroassociation. Changes in solubility properties, diffusion coefficient, relaxation time and decomposition kinetics were evaluated as a function of the anion structure, for the ILs of 1,8-bis (3-methylimidazol-1-yl) octane cation ([BisOct(MIM)2]2+). The results showed that the partition constant decreases according to the anion in the following order: [BF4]- > [SCN]- > [NO3]- > [Br]- > [Cl]-. Thermal stability is also associated with the anion, in which [BisOct(MIM)2][2NO3] is the most stable IL. On the other hand, the diffusion coefficient data did not vary according to the anion under the conditions tested. The kinetics of the decomposition of dicationic ILs ([BisAlq(MIM)2][2Br]) with different alkyl chain length (10, 12 and 14 carbons) was also evaluated and compared with monocationic analogues. It has been found that the stability is not related with the number of carbons in the structure and that the dicationic IL are more stable than monocationic analogs. The organization and morphology of aggregates of dicationic ILs [BisOct(MIM)2][2X], in which X = Br, NO3, BF4 and SCN, were investigated. It has been observed that the cation alkyl spacer chain is folded, forming spherical aggregates and, that interactions occurring on the aggregate’s surface are dependent on the anions type. Thermodynamic parameters of the aggregation process (ΔG°a, ΔH°a and TΔS°a) determined for [BisOct(MIM)2][2Br] showed that the process is enthalpy driven. In addition, it has been observed that as the temperature increases, the free energy of aggregation (ΔG°a) decreases and the free energy of adsorption increases (ΔG°ads) indicating that the aggregation hability decreases and the IL adsorption at the liquid/air interface increases. In the study of heteroassociation, it was investigated heteroassociation of dicationic ILs with different active pharmaceutical ingredients (APIs): salicylic acid (AS), ibuprofen (Ibu) and Paracetamol (Par). It was observed that ILs and IFAs interact at low concentrations (~2 mM) in ethanol-water solution (1:1, v/v). At high concentrations (~50 mM), the APIs were found to interact probably at aggregates surface of the ILs. Interactions between ILs and APIs have also been proven with both components in the solid state. The supramolecular structure of the system [BisOct(MIM)2][2Br] + AS was obtained by monocrystal X-ray diffraction.Este estudo apresenta a influência da estrutura molecular de líquidos iônicos (LIs) dicatiônicos derivados do imidazol nas propriedades físico-químicas, na autoassociação e na heteroassociação. As mudanças nas propriedades de solubilidade, coeficiente de difusão, tempo de relaxação e cinética de decomposição foram avaliadas em função da estrutura do ânion, para os LIs formados pelo cátion 1,8-bis(3-metilimidazol-1-il)octano ([BisOct(MIM)2]2+). Os resultados mostraram que a constante de partição diminui de acordo com o ânion na seguinte ordem: [BF4]- > [SCN]- > [NO3]- > [Br]- > [Cl]-. A estabilidade térmica também está associada ao ânion, sendo o [BisOct(MIM)2][2NO3] o LI mais estável. Por outro lado, os dados de coeficiente de difusão não variaram de acordo com o ânion nas condições testadas. A cinética de decomposição de LIs dicatiônicos ([BisAlq(MIM)2][2Br]) com diferentes tamanhos de cadeia alquílica (10, 12 e 14 carbonos) também foi avaliada e comparada com análogos monocatiônicos. Verificou-se que a estabilidade não está relacionada com o número de carbonos da estrutura e que LIs dicatiônicos são mais estáveis que análogos monocatiônicos. A organização e a morfologia de agregados de LIs dicatiônicos [BisOct(MIM)2][2X], em que X = Br, NO3, BF4 e SCN, foi investigada. Foi observado que a cadeia alquílica espaçadora do cátion está dobrada, formando agregados esféricos. Além disso, as interações que ocorrem na superfície do agregado são dependentes do tipo de ânion. Parâmetros termodinâmicos do processo de agregação (ΔG°a, ΔH°a e TΔS°a) determinados para o [BisOct(MIM)2][2Br] mostraram que a agregação é entalpicamente dirigida. Além disso, observou-se que o aumento da temperatura leva a diminuição da energia livre de agregação (ΔG°a) e ao aumento da energia livre de adsorção (ΔG°ads) indicando que a capacidade de agregação diminui e a adsorção na interface líquido/ar aumenta. A heteroassociação de LIs dicatiônicos com diferentes ingredientes farmacologicamente ativos (IFAs): ácido salicílico (AS), ibuprofeno (Ibu) e paracetamol (Par) foi investigada. Observou-se que LIs e IFAs interagem em concentrações baixas (~2 mM) em solução etanol-água (1:1, vv). Em concentrações elevadas de LI (~50 mM), observou-se que os IFAs interagem, provavelmente, na superfície dos agregados. Interações entre LIs e IFAs também foram comprovadas no estado sólido. A estrutura supramolecular do sistema [BisOct(MIM)2][2Br] + AS foi obtida por difração de raios X de monocristal.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessLíquidos iônicosSolubilidadeCinéticaEstabilidadeAutoassociaçãoHeteroassociaçãoAgregaçãoIonic liquidsSolubilityKineticsStabilityAutoassociationHeteroassociationAggregationCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICALíquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacosinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisFrizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491Martins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Villetti, Marcos Antoniohttp://lattes.cnpq.br/8504489050993642Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Bianchi, Otáviohttp://lattes.cnpq.br/0309287112277751Verly, Rodrigo Moreirahttp://lattes.cnpq.br/9970931211285890http://lattes.cnpq.br/5525102790556947Bender, Caroline Raquel1006000000006008339c8fa-17c5-4531-bcb5-111d15cb015c7fd3d400-4a8e-4e34-b3a1-8f72f0f790c350c581cd-b8f5-4988-a3f5-6c12e2e88fa6e6eb13a6-e907-4f66-a425-e079964588f6f0970438-aab7-4bbe-8d26-13140ae7303ad61d0031-32fe-4300-8065-2bf43b67f7346de6de1e-53bc-472d-aa88-5cce9ef8ad92reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2018_BENDER_CAROLINE.pdfTES_PPGQUIMICA_2018_BENDER_CAROLINE.pdfTese de Doutoradoapplication/pdf45869120http://repositorio.ufsm.br/bitstream/1/14096/1/TES_PPGQUIMICA_2018_BENDER_CAROLINE.pdfabb03639d8e3c00b5af9759760e1bdf0MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
title |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
spellingShingle |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos Bender, Caroline Raquel Líquidos iônicos Solubilidade Cinética Estabilidade Autoassociação Heteroassociação Agregação Ionic liquids Solubility Kinetics Stability Autoassociation Heteroassociation Aggregation CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
title_full |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
title_fullStr |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
title_full_unstemmed |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
title_sort |
Líquidos iônicos dicatiônicos: propriedades físicoquímicas e interações com fármacos |
author |
Bender, Caroline Raquel |
author_facet |
Bender, Caroline Raquel |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0029279904716491 |
dc.contributor.advisor-co1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee1.fl_str_mv |
Villetti, Marcos Antonio |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/8504489050993642 |
dc.contributor.referee2.fl_str_mv |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/6536519955416085 |
dc.contributor.referee3.fl_str_mv |
Bianchi, Otávio |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/0309287112277751 |
dc.contributor.referee4.fl_str_mv |
Verly, Rodrigo Moreira |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/9970931211285890 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5525102790556947 |
dc.contributor.author.fl_str_mv |
Bender, Caroline Raquel |
contributor_str_mv |
Frizzo, Clarissa Piccinin Martins, Marcos Antonio Pinto Villetti, Marcos Antonio Rodrigues, Oscar Endrigo Dorneles Bianchi, Otávio Verly, Rodrigo Moreira |
dc.subject.por.fl_str_mv |
Líquidos iônicos Solubilidade Cinética Estabilidade Autoassociação Heteroassociação Agregação |
topic |
Líquidos iônicos Solubilidade Cinética Estabilidade Autoassociação Heteroassociação Agregação Ionic liquids Solubility Kinetics Stability Autoassociation Heteroassociation Aggregation CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Ionic liquids Solubility Kinetics Stability Autoassociation Heteroassociation Aggregation |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This study presents the influence of the molecular structure of dicationic ionic liquids (ILs) derived from imidazolium ring, on physicochemical properties, self-association and heteroassociation. Changes in solubility properties, diffusion coefficient, relaxation time and decomposition kinetics were evaluated as a function of the anion structure, for the ILs of 1,8-bis (3-methylimidazol-1-yl) octane cation ([BisOct(MIM)2]2+). The results showed that the partition constant decreases according to the anion in the following order: [BF4]- > [SCN]- > [NO3]- > [Br]- > [Cl]-. Thermal stability is also associated with the anion, in which [BisOct(MIM)2][2NO3] is the most stable IL. On the other hand, the diffusion coefficient data did not vary according to the anion under the conditions tested. The kinetics of the decomposition of dicationic ILs ([BisAlq(MIM)2][2Br]) with different alkyl chain length (10, 12 and 14 carbons) was also evaluated and compared with monocationic analogues. It has been found that the stability is not related with the number of carbons in the structure and that the dicationic IL are more stable than monocationic analogs. The organization and morphology of aggregates of dicationic ILs [BisOct(MIM)2][2X], in which X = Br, NO3, BF4 and SCN, were investigated. It has been observed that the cation alkyl spacer chain is folded, forming spherical aggregates and, that interactions occurring on the aggregate’s surface are dependent on the anions type. Thermodynamic parameters of the aggregation process (ΔG°a, ΔH°a and TΔS°a) determined for [BisOct(MIM)2][2Br] showed that the process is enthalpy driven. In addition, it has been observed that as the temperature increases, the free energy of aggregation (ΔG°a) decreases and the free energy of adsorption increases (ΔG°ads) indicating that the aggregation hability decreases and the IL adsorption at the liquid/air interface increases. In the study of heteroassociation, it was investigated heteroassociation of dicationic ILs with different active pharmaceutical ingredients (APIs): salicylic acid (AS), ibuprofen (Ibu) and Paracetamol (Par). It was observed that ILs and IFAs interact at low concentrations (~2 mM) in ethanol-water solution (1:1, v/v). At high concentrations (~50 mM), the APIs were found to interact probably at aggregates surface of the ILs. Interactions between ILs and APIs have also been proven with both components in the solid state. The supramolecular structure of the system [BisOct(MIM)2][2Br] + AS was obtained by monocrystal X-ray diffraction. |
publishDate |
2018 |
dc.date.accessioned.fl_str_mv |
2018-08-24T19:25:08Z |
dc.date.available.fl_str_mv |
2018-08-24T19:25:08Z |
dc.date.issued.fl_str_mv |
2018-01-26 |
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/1/14096 |
url |
http://repositorio.ufsm.br/handle/1/14096 |
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 |
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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 |
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repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
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1793240026584186880 |