Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/16078 |
Resumo: | This thesis describes the synthesis, structural study and antimycobacterial evaluation of a series of novel 4-(alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-2,3-triazoles having as substituent aryl = phenyl, 4- aminophenyl, 3-methoxyphenyl and alkyl = n-hexyl and hydroxymethyl, for the cycloalkanes corresponding to cyclopentane, cyclohexane and cycloheptane. The regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles was performed from 4-azidospiro [chroman-2,1'-cycloalkanes], which in reactions with different terminal alkynes provided cycloaddition reactions 1,3-dipolar regioselective (Click Chemistry) leading to formation of the above-mentioned 1H-1,2,3-triazoles in yields of 47-97%. The novel series of azido spirocycloalkanes precursors were previously obtained in yields of 60-80%, starting from nucleophilic substitution reaction involving a series of 4-mesyl spirochromanes and sodium azide. It is necessary to optimize the reaction conditions due to the occurrence of competition between nucleophilic substitution reactions, which led to the desired azides and elimination, which led to the respective alkenes. The precursor series of 4-mesyl spirochromanes was obtained in two reaction steps comprising a reduction of the respective spiro-chromanones with NaBH4, followed by a mesylation reaction of the secondary alcohols initially originated with mesyl chloride (67-85%). In order to obtain fluorine-derived compounds, fluorination reactions were performed from examples of 1-(spiro [chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazol-4-yl)methanol which led to the formation of a new series of 4-(fluoroethyl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles using DAST as a fluorinating agent in yields of 60-73%. The structural study of the novel molecules isolated during this dissertation was performed using 1H, 13C, 19F NMR, 2D 1H-13C HSQC and 1H-13C HMBC NMR, mass spectrometry and by single crystal X-ray diffraction. The present study evaluate the antimicrobial activity of 4-azido-spiro[chroman-2,1'-cycloalkanes] and 4- (alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles, which showed low activity at the highest concentrations evaluated against the strain of Micobacterium tubeculusis [H37Rv (ATCC 27294)], with MICs > 20-80 μg/mL versus Isoniazid (MIC 0.31 μg/mL) for both series. |
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2019-04-05T13:35:38Z2019-04-05T13:35:38Z2018-08-03http://repositorio.ufsm.br/handle/1/16078This thesis describes the synthesis, structural study and antimycobacterial evaluation of a series of novel 4-(alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-2,3-triazoles having as substituent aryl = phenyl, 4- aminophenyl, 3-methoxyphenyl and alkyl = n-hexyl and hydroxymethyl, for the cycloalkanes corresponding to cyclopentane, cyclohexane and cycloheptane. The regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles was performed from 4-azidospiro [chroman-2,1'-cycloalkanes], which in reactions with different terminal alkynes provided cycloaddition reactions 1,3-dipolar regioselective (Click Chemistry) leading to formation of the above-mentioned 1H-1,2,3-triazoles in yields of 47-97%. The novel series of azido spirocycloalkanes precursors were previously obtained in yields of 60-80%, starting from nucleophilic substitution reaction involving a series of 4-mesyl spirochromanes and sodium azide. It is necessary to optimize the reaction conditions due to the occurrence of competition between nucleophilic substitution reactions, which led to the desired azides and elimination, which led to the respective alkenes. The precursor series of 4-mesyl spirochromanes was obtained in two reaction steps comprising a reduction of the respective spiro-chromanones with NaBH4, followed by a mesylation reaction of the secondary alcohols initially originated with mesyl chloride (67-85%). In order to obtain fluorine-derived compounds, fluorination reactions were performed from examples of 1-(spiro [chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazol-4-yl)methanol which led to the formation of a new series of 4-(fluoroethyl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles using DAST as a fluorinating agent in yields of 60-73%. The structural study of the novel molecules isolated during this dissertation was performed using 1H, 13C, 19F NMR, 2D 1H-13C HSQC and 1H-13C HMBC NMR, mass spectrometry and by single crystal X-ray diffraction. The present study evaluate the antimicrobial activity of 4-azido-spiro[chroman-2,1'-cycloalkanes] and 4- (alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles, which showed low activity at the highest concentrations evaluated against the strain of Micobacterium tubeculusis [H37Rv (ATCC 27294)], with MICs > 20-80 μg/mL versus Isoniazid (MIC 0.31 μg/mL) for both series.Esta dissertação descreve a síntese, estudo estrutural e avaliação antimicobacteriana de uma série de novos 4-(alquil/aril)-1-(espiro[croman-2,1'-cicloalcan]-4-il)-1H-1,2,3-triazóis tendo como substituinte arila = fenil, 4- aminofenil, 3-metóxifenil e alquila = n-hexil e hidroximetil, para os cicloalcanos correspondentes a ciclopentano, ciclohexano e cicloheptano. A síntese regioseletiva de 1,2,3-triazóis 1,4-dissubstituídos foi realizada a partir de 4-azidoespiro[croman- 2,1’-cicloalcanos], que por sua vez, em reações com diferentes alcinos terminais proporcionaram reações de cicloadição 1,3-dipolar regiosseletivas (Click Chemistry) levando a formação dos 1H-1,2,3-triazóis supracitados em rendimentos de 47-97%. A série inédita de azido espirocicloalcanos precursores foi previamente obtida em rendimentos de 60-80%, a partir, de reação de substituição nucleofílica envolvendo uma série de 4-mesil espirocromanos e azida de sódio. Salienta-se a necessidade de otimização das condições reacionais devido à ocorrência de competição entre reações de substituição nucleofílica, que conduziram às azidas desejadas e de eliminação, que levavam aos alceno respectivos. A série precursora de 4-mesil espiro-cromanos foi obtida em dois passos reacionais compreendendo uma redução das respectivas espiro-cromanonas com NaBH4, seguida de uma reação de mesilação dos álcoois secundários inicialmente originados com cloreto de mesila (67-85%). Visando a obtenção de compostos flúor derivados, foram realizadas reações de fluoração a partir de exemplos de 1-(espiro[croman-2,1'-cicloalcan]-4-il)-1H-1,2,3-triazol-4-il)metanol, que levaram à formação de uma nova série de 4-(fluormetil)-1-(espiro[croman-2,1'-cicloalcan]-4-il)-1H-1,2,3-triazóis utilizando DAST como agente fluorante, em rendimentos de 60-73%. O estudo estrutural das moléculas inéditas isoladas no decorrer desta dissertação foi realizado utilizando técnicas de RMN de 1H, 13C, 19F, RMN 2D 1H-13C HSQC e 1H-13C HMBC, espectrometria de massas e difração de raios X de monocristal. Visando uma futura aplicação dos produtos obtidos, realizou-se a avaliação da atividade antimicrobiana das séries de 4-azido-espiro[croman-2,1’-cicloalcanos] e 4-(alquil/aril)-1-(espiro[croman-2,1'-cicloalcan]-4-il)-1H- 1,2,3-triazóis, as quais apresentaram baixa atividade nas maiores concentrações avaliadas frente a cepa de Micobacterium tubeculusis [H37Rv (ATCC 27294)], constatando-se MICs > 20-80 μg/mL versus o padrão Isoniazida (MIC 0,31 μg/mL) para ambas as séries.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/openAccessTriazóisEspiro heterociclosCromenonasTriazolesSpiro heterocyclesChromenonesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóisSynthesis, structure and antimicobacterial evaluation of new 1-(spiro[chroman-2,1'-cycloalcan]-4-yl)-1h-1,2,3-triazoleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Machado, Pablohttp://lattes.cnpq.br/3319303431365448Souza, Diego dehttp://lattes.cnpq.br/3561369550388349http://lattes.cnpq.br/5739053525357685Stefanello, Felipe Salvador10060000000060006c852ad-d805-43c3-99d6-93a6a86f507cb51e5b9a-37ea-4550-8a4c-fa623585e740d5c48bba-82b0-4561-b72d-03f85576dc0c652bbc70-0693-40b4-abca-8f72baa2910areponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdfDIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdfDissertação de Mestradoapplication/pdf15891918http://repositorio.ufsm.br/bitstream/1/16078/1/DIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdfa6e968244081f4bedc85d8a2520a57fdMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
dc.title.alternative.eng.fl_str_mv |
Synthesis, structure and antimicobacterial evaluation of new 1-(spiro[chroman-2,1'-cycloalcan]-4-yl)-1h-1,2,3-triazole |
title |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
spellingShingle |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis Stefanello, Felipe Salvador Triazóis Espiro heterociclos Cromenonas Triazoles Spiro heterocycles Chromenones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
title_full |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
title_fullStr |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
title_full_unstemmed |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
title_sort |
Síntese, estrutura e avaliação antimicobacteriana de novos 1- (espiro[croman-2,1’-cicloalcan]-4-il)-1h-1,2,3-triazóis |
author |
Stefanello, Felipe Salvador |
author_facet |
Stefanello, Felipe Salvador |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Machado, Pablo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3319303431365448 |
dc.contributor.referee2.fl_str_mv |
Souza, Diego de |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/3561369550388349 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5739053525357685 |
dc.contributor.author.fl_str_mv |
Stefanello, Felipe Salvador |
contributor_str_mv |
Bonacorso, Helio Gauze Machado, Pablo Souza, Diego de |
dc.subject.por.fl_str_mv |
Triazóis Espiro heterociclos Cromenonas |
topic |
Triazóis Espiro heterociclos Cromenonas Triazoles Spiro heterocycles Chromenones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Triazoles Spiro heterocycles Chromenones |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This thesis describes the synthesis, structural study and antimycobacterial evaluation of a series of novel 4-(alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-2,3-triazoles having as substituent aryl = phenyl, 4- aminophenyl, 3-methoxyphenyl and alkyl = n-hexyl and hydroxymethyl, for the cycloalkanes corresponding to cyclopentane, cyclohexane and cycloheptane. The regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles was performed from 4-azidospiro [chroman-2,1'-cycloalkanes], which in reactions with different terminal alkynes provided cycloaddition reactions 1,3-dipolar regioselective (Click Chemistry) leading to formation of the above-mentioned 1H-1,2,3-triazoles in yields of 47-97%. The novel series of azido spirocycloalkanes precursors were previously obtained in yields of 60-80%, starting from nucleophilic substitution reaction involving a series of 4-mesyl spirochromanes and sodium azide. It is necessary to optimize the reaction conditions due to the occurrence of competition between nucleophilic substitution reactions, which led to the desired azides and elimination, which led to the respective alkenes. The precursor series of 4-mesyl spirochromanes was obtained in two reaction steps comprising a reduction of the respective spiro-chromanones with NaBH4, followed by a mesylation reaction of the secondary alcohols initially originated with mesyl chloride (67-85%). In order to obtain fluorine-derived compounds, fluorination reactions were performed from examples of 1-(spiro [chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazol-4-yl)methanol which led to the formation of a new series of 4-(fluoroethyl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles using DAST as a fluorinating agent in yields of 60-73%. The structural study of the novel molecules isolated during this dissertation was performed using 1H, 13C, 19F NMR, 2D 1H-13C HSQC and 1H-13C HMBC NMR, mass spectrometry and by single crystal X-ray diffraction. The present study evaluate the antimicrobial activity of 4-azido-spiro[chroman-2,1'-cycloalkanes] and 4- (alkyl/aryl)-1-(spiro[chroman-2,1'-cycloalkan]-4-yl)-1H-1,2,3-triazoles, which showed low activity at the highest concentrations evaluated against the strain of Micobacterium tubeculusis [H37Rv (ATCC 27294)], with MICs > 20-80 μg/mL versus Isoniazid (MIC 0.31 μg/mL) for both series. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-08-03 |
dc.date.accessioned.fl_str_mv |
2019-04-05T13:35:38Z |
dc.date.available.fl_str_mv |
2019-04-05T13:35:38Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/16078 |
url |
http://repositorio.ufsm.br/handle/1/16078 |
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 |
06c852ad-d805-43c3-99d6-93a6a86f507c b51e5b9a-37ea-4550-8a4c-fa623585e740 d5c48bba-82b0-4561-b72d-03f85576dc0c 652bbc70-0693-40b4-abca-8f72baa2910a |
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:Manancial - Repositório Digital da 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 |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/16078/1/DIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdf http://repositorio.ufsm.br/bitstream/1/16078/2/license_rdf http://repositorio.ufsm.br/bitstream/1/16078/3/license.txt http://repositorio.ufsm.br/bitstream/1/16078/4/DIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdf.txt http://repositorio.ufsm.br/bitstream/1/16078/5/DIS_PPGQUIMICA_2018_STEFANELLO_FELIPE.pdf.jpg |
bitstream.checksum.fl_str_mv |
a6e968244081f4bedc85d8a2520a57fd 4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df 81b934549334d9da9751927db892f411 0a56b7a7bdbea156fb8aaef603b9fcd5 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
|
_version_ |
1801223746491514880 |