Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno
Ano de defesa: | 2017 |
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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/1/13615 |
Resumo: | This work presents the study of multicomponent crystals formed by salicylic acid (AS) with 1,2-Phenylenediamine (FEN) and 3-Amino-1,2-4-1H-triazole (TRIA) as amines; and rac-ibuprofen (IBU) with 3-amino-5-methyl-1H-pyrazole (PIR) and tyramine (TIR) as amines. Thus, four new multicomponent crystals were synthesized and characterized by differential scanning calorimetry, infrared spectroscopy, powder X-ray diffraction and single crystals X-ray diffraction. The main intermolecular interaction present in the supramolecular structure of the multicomponent crystals was the hydrogen bonding. This interaction promoted the crystallization of the multicomponent crystals from the formation of (i) a cyclic dimer, formed mainly by the interaction of the carboxylic acid group (AS or IBU) with the aromatic nitrogen and amine group that was characteristic of the multicomponent crystals of the acids with the substituted amino heterocycles (AS...TRIA and IBU...PIR); ii) tetramer formed by interactions of the carboxylic acid (AS or IBU) and amine which was characteristic of the multicomponent crystals of the acids with the primary amines 1,2-phenylenediamine and tyramine (AS...FEN and IBU...TIR). In the cases of dimer formation, the hydrogen bonds between the coformers were characteristic of heterosyntons, differentiating the supramolecular structure of the multicomponent crystals of their coformers and also of other multicomponent crystals already reported in the literature for the same coformers. The stability of the crystal lattice and the dimers and tetramers that governed the supramolecular arrangement of the multicomponent crystals and coformers was determined to evaluate the stability of the molecules in both systems. The results showed that the energy of the crystalline lattice is not the determining factor for the formation of the multicomponent crystal. On the other hand, the energy of the dimers and tetramers that initiated the growth of the crystal and added to it a greater contribution to stability, has been shown to be the factor that defines the growth of the monocomponent or multicomponent crystal. This fact becomes clear when we observe that the multicomponent crystals derived from AS formed more stable heterodimers than the homodimers of the coformers. The IBU-derived crystals formed more stable heterodimers than the homodimers present in the IBU polymorph II, and less stable than the polymorph I homodimer, showing that the crystallization of the IBU in these multicomponent systems occurs by the conversion of the polymorph I to the polymorph II and Then forms the multi-component crystal. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2018-06-28T22:22:02Z2018-06-28T22:22:02Z2017-03-17http://repositorio.ufsm.br/handle/1/13615This work presents the study of multicomponent crystals formed by salicylic acid (AS) with 1,2-Phenylenediamine (FEN) and 3-Amino-1,2-4-1H-triazole (TRIA) as amines; and rac-ibuprofen (IBU) with 3-amino-5-methyl-1H-pyrazole (PIR) and tyramine (TIR) as amines. Thus, four new multicomponent crystals were synthesized and characterized by differential scanning calorimetry, infrared spectroscopy, powder X-ray diffraction and single crystals X-ray diffraction. The main intermolecular interaction present in the supramolecular structure of the multicomponent crystals was the hydrogen bonding. This interaction promoted the crystallization of the multicomponent crystals from the formation of (i) a cyclic dimer, formed mainly by the interaction of the carboxylic acid group (AS or IBU) with the aromatic nitrogen and amine group that was characteristic of the multicomponent crystals of the acids with the substituted amino heterocycles (AS...TRIA and IBU...PIR); ii) tetramer formed by interactions of the carboxylic acid (AS or IBU) and amine which was characteristic of the multicomponent crystals of the acids with the primary amines 1,2-phenylenediamine and tyramine (AS...FEN and IBU...TIR). In the cases of dimer formation, the hydrogen bonds between the coformers were characteristic of heterosyntons, differentiating the supramolecular structure of the multicomponent crystals of their coformers and also of other multicomponent crystals already reported in the literature for the same coformers. The stability of the crystal lattice and the dimers and tetramers that governed the supramolecular arrangement of the multicomponent crystals and coformers was determined to evaluate the stability of the molecules in both systems. The results showed that the energy of the crystalline lattice is not the determining factor for the formation of the multicomponent crystal. On the other hand, the energy of the dimers and tetramers that initiated the growth of the crystal and added to it a greater contribution to stability, has been shown to be the factor that defines the growth of the monocomponent or multicomponent crystal. This fact becomes clear when we observe that the multicomponent crystals derived from AS formed more stable heterodimers than the homodimers of the coformers. The IBU-derived crystals formed more stable heterodimers than the homodimers present in the IBU polymorph II, and less stable than the polymorph I homodimer, showing that the crystallization of the IBU in these multicomponent systems occurs by the conversion of the polymorph I to the polymorph II and Then forms the multi-component crystal.Este trabalho apresenta o estudo de cristais multicomponentes formados pelo ácido salicílico (AS) com 1,2-Fenilenodiamina (FEN) e 3-Amino-1,2-4-1H-triazol (TRIA) como aminas; e pelo rac-ibuprofeno (IBU) com 3-amino-5-metil-1H-pirazol (PIR) e tiramina (TIR) como aminas. Assim, quatro novos cristais multicomponentes foram sintetizados e caracterizados por calorimetria exploratória diferencial, espectroscopia de infravermelho e difração de raios-X em pó e de monocristais. A principal interação intermolecular presente na estrutura supramolecular dos cristais multicomponentes foi a ligação de hidrogênio. Esta interação promoveu a cristalização dos cristais multicomponente a partir da formação de (i) um dímero cíclico, formado principalmente pela interação do grupo ácido carboxílico (AS ou IBU) com o nitrogênio aromático e grupo amina que foi característico dos cristais multicomponentes dos ácidos com os heterociclos amino substituídos (ASTRIA e IBUPIR); (ii) tetrâmero formado por interações do ácido carboxílico (AS ou IBU) e amina que foi característico dos cristais multicomponentes dos ácidos com as aminas primárias 1,2-fenilenodiamina e tiramina (ASFEN e IBUTIR). Nos casos de formação de dímeros, as ligações de hidrogênio entre os coformadores foram características de heterodímeros, diferenciando a estrutura supramolecular dos cristais multicomponentes de seus coformadores e também de outros cristais multicomponentes já relatados na literatura para os mesmos coformadores. A estabilidade da rede cristalina e dos dímeros e tetrâmeros que governaram o arranjo supramolecular dos cristais multicomponentes e dos coformadores foi determinada para avaliar a estabilidade das moléculas em ambos os sistemas. Os resultados mostraram que a energia da rede cristalina não é o fator determinante para a formação do cristal multicomponente. Por outro lado, a energia dos dímeros e tetrâmeros que iniciaram o crescimento do cristal e adicionaram a ele maior contribuição para estabilidade, mostrou ser o fator que define o crescimento do cristal monocomponente ou multicomponente. Este fato fica claro quando observamos que os cristais multicomponentes derivados do AS formaram heterodímeros mais estáveis do que os homodímeros dos coformadores. Os cristais derivados do IBU formaram heterodímeros mais estáveis do que o homodímeros presente no polimorfo II do IBU, e menos estáveis do que o homodímero do polimorfo I, mostrando que a cristalização do IBU nestes sistemas multicomponentes ocorre pela conversão do polimorfo I no polimorfo II e a seguir forma o cristal multicomponente.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccessCristais multicomponentesEstrutura supramolecularDifratometria de raios-XCluster supramolecularMecanismo de cristalizaçãoMulticomponent crystalsSupramolecular structureX-ray diffractionSupramolecular clusterCrystallization mechanismCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAEstrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofenoSupramolecular structure of multicomponent crystals from salicylic acid and ibuprofeninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisFrizzo, Clarissa Piccininhttp://lattes.cnpq.br/0029279904716491Hörner, Manfredohttp://lattes.cnpq.br/8922528250830998Burgo, Thiago Augusto de Limahttp://lattes.cnpq.br/5737213839553155Gomes, Elionai Cassiana de Limahttp://lattes.cnpq.br/2765845361461091Gindri, Izabelle de Mellohttp://lattes.cnpq.br/4116776336088149http://lattes.cnpq.br/0057067030312013Tier, Aniele Zolin1006000000006008339c8fa-17c5-4531-bcb5-111d15cb015cac41c10c-9af0-467f-a8f3-b07c16c1671934252cc3-b6c0-4876-9bb6-6020475d2214ea58280d-c311-4e40-af49-8adb2aeee147128edaa8-cd35-4d77-b9cb-072bceafa9fc6d205525-2e0a-4947-9c1a-3d0a13e827cbreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2017_TIER_ANIELE.pdfTES_PPGQUIMICA_2017_TIER_ANIELE.pdfTese de Doutoradoapplication/pdf9563071http://repositorio.ufsm.br/bitstream/1/13615/1/TES_PPGQUIMICA_2017_TIER_ANIELE.pdf535f424b86886b991e0687254b91241cMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
dc.title.alternative.eng.fl_str_mv |
Supramolecular structure of multicomponent crystals from salicylic acid and ibuprofen |
title |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
spellingShingle |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno Tier, Aniele Zolin Cristais multicomponentes Estrutura supramolecular Difratometria de raios-X Cluster supramolecular Mecanismo de cristalização Multicomponent crystals Supramolecular structure X-ray diffraction Supramolecular cluster Crystallization mechanism CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
title_full |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
title_fullStr |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
title_full_unstemmed |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
title_sort |
Estrutura supramolecular de cristais multicomponentes derivados do ácido salicílico e do ibuprofeno |
author |
Tier, Aniele Zolin |
author_facet |
Tier, Aniele Zolin |
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.referee1.fl_str_mv |
Hörner, Manfredo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/8922528250830998 |
dc.contributor.referee2.fl_str_mv |
Burgo, Thiago Augusto de Lima |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/5737213839553155 |
dc.contributor.referee3.fl_str_mv |
Gomes, Elionai Cassiana de Lima |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/2765845361461091 |
dc.contributor.referee4.fl_str_mv |
Gindri, Izabelle de Mello |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/4116776336088149 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0057067030312013 |
dc.contributor.author.fl_str_mv |
Tier, Aniele Zolin |
contributor_str_mv |
Frizzo, Clarissa Piccinin Hörner, Manfredo Burgo, Thiago Augusto de Lima Gomes, Elionai Cassiana de Lima Gindri, Izabelle de Mello |
dc.subject.por.fl_str_mv |
Cristais multicomponentes Estrutura supramolecular Difratometria de raios-X Cluster supramolecular Mecanismo de cristalização |
topic |
Cristais multicomponentes Estrutura supramolecular Difratometria de raios-X Cluster supramolecular Mecanismo de cristalização Multicomponent crystals Supramolecular structure X-ray diffraction Supramolecular cluster Crystallization mechanism CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Multicomponent crystals Supramolecular structure X-ray diffraction Supramolecular cluster Crystallization mechanism |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work presents the study of multicomponent crystals formed by salicylic acid (AS) with 1,2-Phenylenediamine (FEN) and 3-Amino-1,2-4-1H-triazole (TRIA) as amines; and rac-ibuprofen (IBU) with 3-amino-5-methyl-1H-pyrazole (PIR) and tyramine (TIR) as amines. Thus, four new multicomponent crystals were synthesized and characterized by differential scanning calorimetry, infrared spectroscopy, powder X-ray diffraction and single crystals X-ray diffraction. The main intermolecular interaction present in the supramolecular structure of the multicomponent crystals was the hydrogen bonding. This interaction promoted the crystallization of the multicomponent crystals from the formation of (i) a cyclic dimer, formed mainly by the interaction of the carboxylic acid group (AS or IBU) with the aromatic nitrogen and amine group that was characteristic of the multicomponent crystals of the acids with the substituted amino heterocycles (AS...TRIA and IBU...PIR); ii) tetramer formed by interactions of the carboxylic acid (AS or IBU) and amine which was characteristic of the multicomponent crystals of the acids with the primary amines 1,2-phenylenediamine and tyramine (AS...FEN and IBU...TIR). In the cases of dimer formation, the hydrogen bonds between the coformers were characteristic of heterosyntons, differentiating the supramolecular structure of the multicomponent crystals of their coformers and also of other multicomponent crystals already reported in the literature for the same coformers. The stability of the crystal lattice and the dimers and tetramers that governed the supramolecular arrangement of the multicomponent crystals and coformers was determined to evaluate the stability of the molecules in both systems. The results showed that the energy of the crystalline lattice is not the determining factor for the formation of the multicomponent crystal. On the other hand, the energy of the dimers and tetramers that initiated the growth of the crystal and added to it a greater contribution to stability, has been shown to be the factor that defines the growth of the monocomponent or multicomponent crystal. This fact becomes clear when we observe that the multicomponent crystals derived from AS formed more stable heterodimers than the homodimers of the coformers. The IBU-derived crystals formed more stable heterodimers than the homodimers present in the IBU polymorph II, and less stable than the polymorph I homodimer, showing that the crystallization of the IBU in these multicomponent systems occurs by the conversion of the polymorph I to the polymorph II and Then forms the multi-component crystal. |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017-03-17 |
dc.date.accessioned.fl_str_mv |
2018-06-28T22:22:02Z |
dc.date.available.fl_str_mv |
2018-06-28T22:22:02Z |
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/1/13615 |
url |
http://repositorio.ufsm.br/handle/1/13615 |
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 |
8339c8fa-17c5-4531-bcb5-111d15cb015c ac41c10c-9af0-467f-a8f3-b07c16c16719 34252cc3-b6c0-4876-9bb6-6020475d2214 ea58280d-c311-4e40-af49-8adb2aeee147 128edaa8-cd35-4d77-b9cb-072bceafa9fc 6d205525-2e0a-4947-9c1a-3d0a13e827cb |
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 |
http://repositorio.ufsm.br/bitstream/1/13615/1/TES_PPGQUIMICA_2017_TIER_ANIELE.pdf http://repositorio.ufsm.br/bitstream/1/13615/2/license_rdf http://repositorio.ufsm.br/bitstream/1/13615/3/license.txt http://repositorio.ufsm.br/bitstream/1/13615/4/TES_PPGQUIMICA_2017_TIER_ANIELE.pdf.txt http://repositorio.ufsm.br/bitstream/1/13615/5/TES_PPGQUIMICA_2017_TIER_ANIELE.pdf.jpg |
bitstream.checksum.fl_str_mv |
535f424b86886b991e0687254b91241c c1efe8e24d7281448e873be30ea326ff 2f0571ecee68693bd5cd3f17c1e075df 7f2b75f34e6458026fda68528ee644c2 736f6a65b46973fecd645b21b71f7e6b |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
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 |
_version_ |
1793240047110062080 |