Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas
Ano de defesa: | 2022 |
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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/1/26690 |
Resumo: | The present thesis reports the reactivity study between 5-bromo-1,1,1,-trifluoro-4- methoxy(amino)pent-3-en-2-ones (5-bromoenones/enaminones) towards 5- or 6- substituted 4-(trihalomethyl)pyrimidin-2(1H)-ones. During the initial tests, it was found that the chemoselectivity of the reaction (selective towards N- or O-alkylation) is highly influenced by the presence or absence of a substituent at the 6- position of the starting pyrimidin-2(1H)-one. In this manner, 10 N-alkylated and 25 O-alkylated products were prepared as sole compounds, with full selectivity, in 60 – 94% yields. In a second moment, the β-enaminone moiety present in the alkylated products was cyclocondensed with NO-, NN- e NCN-dinucleophiles, with the aim of obtaining conjugated isoxazoles, pyrazoles and pyrimidines. In this sense, 4 N-azolylmethyl-pyrimidin-2(1H)-2-ones and 6- O-azolylmethyl-pyrimidines were obtained through cyclocondensation reactions of type [3+2] in satisfactory yields. When 2-methylisothiourea sulfate was used to perform the [3+3] cyclocondensation reaction, yields of 8 – 10% were observed. As to overcome this, a convergent synthetic strategy was used, by preparing, isolated, 4-(halomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines through the cyclocondensation between 5-bromo-1,1,1-trifluoro(chloro)-4-methoxypent-3-en-2-ones and 2-methylisothiourea sulfate, which are obtained in 59 – 85% yields. These halomethyl pyrimidines are used as electrophiles that insert the pyrimidine nucleus as heterocyclic block previously prepared. The selectivity of the reaction was maintained the same as in the first synthetic step of this study, and, when reacted with 4-(trifluoromethyl)pyrimidin-2(1H)-ones, only the O-alkylation products were obtained in the presence of a substituent at the 6-position. In this step, the electrophile used in the alkylation reaction was also evaluated, thus (4- chloro/bromo/iodomethyl)pyrimidines were prepared and the 4-(iodomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines were found to be the ones that react faster and more efficient for this reaction type. In this manner, 18 O-alkylated derivatives were prepared in yields 70 – 98%. In the absence of a substituent at the 6-position, the expected N-alkylated products could not be obtained through any of the proposed methodologies. Keywords: Pyrimidinones, enones, heterocycles, alkylation, selective reaction. |
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2022-10-27T15:46:16Z2022-10-27T15:46:16Z2022-09-23http://repositorio.ufsm.br/handle/1/26690The present thesis reports the reactivity study between 5-bromo-1,1,1,-trifluoro-4- methoxy(amino)pent-3-en-2-ones (5-bromoenones/enaminones) towards 5- or 6- substituted 4-(trihalomethyl)pyrimidin-2(1H)-ones. During the initial tests, it was found that the chemoselectivity of the reaction (selective towards N- or O-alkylation) is highly influenced by the presence or absence of a substituent at the 6- position of the starting pyrimidin-2(1H)-one. In this manner, 10 N-alkylated and 25 O-alkylated products were prepared as sole compounds, with full selectivity, in 60 – 94% yields. In a second moment, the β-enaminone moiety present in the alkylated products was cyclocondensed with NO-, NN- e NCN-dinucleophiles, with the aim of obtaining conjugated isoxazoles, pyrazoles and pyrimidines. In this sense, 4 N-azolylmethyl-pyrimidin-2(1H)-2-ones and 6- O-azolylmethyl-pyrimidines were obtained through cyclocondensation reactions of type [3+2] in satisfactory yields. When 2-methylisothiourea sulfate was used to perform the [3+3] cyclocondensation reaction, yields of 8 – 10% were observed. As to overcome this, a convergent synthetic strategy was used, by preparing, isolated, 4-(halomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines through the cyclocondensation between 5-bromo-1,1,1-trifluoro(chloro)-4-methoxypent-3-en-2-ones and 2-methylisothiourea sulfate, which are obtained in 59 – 85% yields. These halomethyl pyrimidines are used as electrophiles that insert the pyrimidine nucleus as heterocyclic block previously prepared. The selectivity of the reaction was maintained the same as in the first synthetic step of this study, and, when reacted with 4-(trifluoromethyl)pyrimidin-2(1H)-ones, only the O-alkylation products were obtained in the presence of a substituent at the 6-position. In this step, the electrophile used in the alkylation reaction was also evaluated, thus (4- chloro/bromo/iodomethyl)pyrimidines were prepared and the 4-(iodomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines were found to be the ones that react faster and more efficient for this reaction type. In this manner, 18 O-alkylated derivatives were prepared in yields 70 – 98%. In the absence of a substituent at the 6-position, the expected N-alkylated products could not be obtained through any of the proposed methodologies. Keywords: Pyrimidinones, enones, heterocycles, alkylation, selective reaction.A presente tese relata o estudo da reatividade de 5-bromo-1,1,1-trifluor-4- metoxi(amino)pent-3-en-2-onas (5-bromo enonas/enaminonas) frente a 4- (trialometil)pirimidin-2(1H)-onas 5- ou 6-substituídas. Durante os estudos iniciais, verificou-se que a quimioseletividade da reação de alquilação (seletiva para N- ou Oalquilação) é altamente influenciada pela presença ou ausência de substituinte na posição 6- do anel da pirimidin-2(1H)-ona de partida. Assim, 10 produtos N-alquilados e 25 produtos O-alquilados foram preparados isoladamente, com seletividade total, em rendimentos de 60 – 94%. Em um segundo momento, a β-enaminona presente nos produtos foi ciclocondensada com NO-, NN- e NCN-dinucleófilos, a fim de se obter isoxazóis, pirazóis e pirimidinas conjugadas. Foram obtidos 4 N-azolilmetil-pirimidin2(1H)-onas e 6 O-azolilmetil-pirimidinas através de reações de ciclocondensação do tipo [3+2] em rendimentos satisfatórios (55 – 83%). Quando sulfato de 2-metilisotiouréia foi utilizado para fazer promover a reação de ciclocondensação do tipo [3+3], foram observados rendimentos de 8 – 10%. A fim de superar o baixo rendimento obtido através da estratégia da ciclocondensação direta do produto O-alquilado previamente obtido, foi utilizada uma estratégia convergente de síntese, preparando, isoladamente, 4-(halometil)- 2-(metilsulfanil)-6-(trialometil)pirimidinas através da ciclocondensação entre 5-bromo1,1,1-trifluor(cloro)-4-metoxipent-3-en-2-onas e sulfato de 2-metilisotiouréia, que são obtidas em rendimentos satisfatórios (59 – 85%). Estas pirimidinas halometiladas são usadas como eletrófilos que inserem o núcleo pirimidínico como um bloco heterocíclico previamente preparado. A seletividade da reação se manteve idêntica à primeira parte deste estudo, e, ao serem reagidas com 4-(trifluormetil)pirimidin-2(1H)-onas, somente produtos de O-alquilação foram obtidos na presença de um substituinte na posição 6-. Nesta etapa do estudo também foi feita a avaliação do eletrófilo utilizado nas reações de alquilação e (4-cloro/bromo/iodometil)pirimidinas foram preparadas e, foi identificado que para esta reação, as 4-(iodometil)-2-(metilsulfanil)-6-(trialometil)pirimidinas reagem de maneira mais rápida e eficiente, sendo que 18 derivados O-alquilados foram preparados com rendimentos 70 – 98%.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/openAccessPirimidinonasEnonasHeterociclosAlquilaçãoReação seletivaPyrimidinonesEnonesHeterocyclesAlkylationSelective reactionCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICARegioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonasRegiochemistry of the alkylation reaction between 4-(trihalomethyl)pyrimidin-2(1h)-ones and 5-bromoenonesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Martins, Marcos Antonio PintoWessjohann, Ludger AloisiusRosa, Fernanda AndreiaFrizzo, Clarissa PiccininSchumacher, Ricardo Fredericohttp://lattes.cnpq.br/7341503512916041Mittersteiner, Mateus100600000000600600600600600600600600233dc1de-ab03-4f57-9b85-e40dc01a2d4fc9c2a799-83c4-429c-8887-b1607dbb636d50c581cd-b8f5-4988-a3f5-6c12e2e88fa68f844ed3-ad63-44dd-9342-1275dbd22598d8662a5f-28f9-41c1-a6af-67b2581ef1d49092def2-f6f8-4a85-9d6a-97dbdb8e53a86c8d4d2c-6e7a-4fa7-8f85-f8e27a24863breponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2022_MITTERSTEINER_MATEUS.pdfTES_PPGQUÍMICA_2022_MITTERSTEINER_MATEUS.pdfTese de doutoradoapplication/pdf30290179http://repositorio.ufsm.br/bitstream/1/26690/1/TES_PPGQU%c3%8dMICA_2022_MITTERSTEINER_MATEUS.pdf5d7d9b079e1c723a920324f7973879d5MD51LICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
dc.title.alternative.eng.fl_str_mv |
Regiochemistry of the alkylation reaction between 4-(trihalomethyl)pyrimidin-2(1h)-ones and 5-bromoenones |
title |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
spellingShingle |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas Mittersteiner, Mateus Pirimidinonas Enonas Heterociclos Alquilação Reação seletiva Pyrimidinones Enones Heterocycles Alkylation Selective reaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
title_full |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
title_fullStr |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
title_full_unstemmed |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
title_sort |
Regioquímica da reação de alquilação entre 4- (trialometil)pirimidin-2(1h)-onas e 5-bromoenonas |
author |
Mittersteiner, Mateus |
author_facet |
Mittersteiner, Mateus |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.advisor-co1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.referee1.fl_str_mv |
Wessjohann, Ludger Aloisius |
dc.contributor.referee2.fl_str_mv |
Rosa, Fernanda Andreia |
dc.contributor.referee3.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee4.fl_str_mv |
Schumacher, Ricardo Frederico |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7341503512916041 |
dc.contributor.author.fl_str_mv |
Mittersteiner, Mateus |
contributor_str_mv |
Zanatta, Nilo Martins, Marcos Antonio Pinto Wessjohann, Ludger Aloisius Rosa, Fernanda Andreia Frizzo, Clarissa Piccinin Schumacher, Ricardo Frederico |
dc.subject.por.fl_str_mv |
Pirimidinonas Enonas Heterociclos Alquilação Reação seletiva |
topic |
Pirimidinonas Enonas Heterociclos Alquilação Reação seletiva Pyrimidinones Enones Heterocycles Alkylation Selective reaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Pyrimidinones Enones Heterocycles Alkylation Selective reaction |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present thesis reports the reactivity study between 5-bromo-1,1,1,-trifluoro-4- methoxy(amino)pent-3-en-2-ones (5-bromoenones/enaminones) towards 5- or 6- substituted 4-(trihalomethyl)pyrimidin-2(1H)-ones. During the initial tests, it was found that the chemoselectivity of the reaction (selective towards N- or O-alkylation) is highly influenced by the presence or absence of a substituent at the 6- position of the starting pyrimidin-2(1H)-one. In this manner, 10 N-alkylated and 25 O-alkylated products were prepared as sole compounds, with full selectivity, in 60 – 94% yields. In a second moment, the β-enaminone moiety present in the alkylated products was cyclocondensed with NO-, NN- e NCN-dinucleophiles, with the aim of obtaining conjugated isoxazoles, pyrazoles and pyrimidines. In this sense, 4 N-azolylmethyl-pyrimidin-2(1H)-2-ones and 6- O-azolylmethyl-pyrimidines were obtained through cyclocondensation reactions of type [3+2] in satisfactory yields. When 2-methylisothiourea sulfate was used to perform the [3+3] cyclocondensation reaction, yields of 8 – 10% were observed. As to overcome this, a convergent synthetic strategy was used, by preparing, isolated, 4-(halomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines through the cyclocondensation between 5-bromo-1,1,1-trifluoro(chloro)-4-methoxypent-3-en-2-ones and 2-methylisothiourea sulfate, which are obtained in 59 – 85% yields. These halomethyl pyrimidines are used as electrophiles that insert the pyrimidine nucleus as heterocyclic block previously prepared. The selectivity of the reaction was maintained the same as in the first synthetic step of this study, and, when reacted with 4-(trifluoromethyl)pyrimidin-2(1H)-ones, only the O-alkylation products were obtained in the presence of a substituent at the 6-position. In this step, the electrophile used in the alkylation reaction was also evaluated, thus (4- chloro/bromo/iodomethyl)pyrimidines were prepared and the 4-(iodomethyl)-2- (methylsulfanyl)-6-(trihalomethyl)pyrimidines were found to be the ones that react faster and more efficient for this reaction type. In this manner, 18 O-alkylated derivatives were prepared in yields 70 – 98%. In the absence of a substituent at the 6-position, the expected N-alkylated products could not be obtained through any of the proposed methodologies. Keywords: Pyrimidinones, enones, heterocycles, alkylation, selective reaction. |
publishDate |
2022 |
dc.date.accessioned.fl_str_mv |
2022-10-27T15:46:16Z |
dc.date.available.fl_str_mv |
2022-10-27T15:46:16Z |
dc.date.issued.fl_str_mv |
2022-09-23 |
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/1/26690 |
url |
http://repositorio.ufsm.br/handle/1/26690 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
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) |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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http://repositorio.ufsm.br/bitstream/1/26690/1/TES_PPGQU%c3%8dMICA_2022_MITTERSTEINER_MATEUS.pdf http://repositorio.ufsm.br/bitstream/1/26690/3/license.txt http://repositorio.ufsm.br/bitstream/1/26690/2/license_rdf |
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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 |
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1793240133904891904 |