Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro
Ano de defesa: | 2013 |
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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
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Departamento: |
Química
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País: |
Brasil
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Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/28257 |
Resumo: | Multi-nitrogenated ligands are versatile coordinating ligands to the transition metals. In this work, mono- and bis-triazenes, a tris-triazene, a tetrazenide and twelve metal complexes were synthesized, including the metal ions Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) and Cu(III). The triazenes and complexes were characterized by different analysis: infrared and UV-Vis spectroscopy, 1H, 13C and 31P NMR spectroscopy, low or high resolution mass spectrometry (EI, ESI, ESI(+)-TOF and ESI(-)-TOF) and X-ray diffraction on single crystal. The Cu(II) complex of the mono-triazenide N-oxide ligand [(2-Ph)ArNNN(®O)CH3]- (2) shows cis geometry on the coordinated center and possesses intramolecular Cu(II)···arene- interactions. Four complexes [(R’)ArNNNAr(R’’)Au(I)PPh3] were synthesized: 4 (R’ = OCH3, R’’ = 2-Ph), 6 (R’ = R’’ = 2-Ph), 8 (R’ = R’’ = 4-C(O)NH2) e 10 (R’ = 2-F, R’’ = 4-C(O)NH2). The crystal structure of 6 shows intramolecular Au(I)···arene- interaction. The complexes 8 and 10 are biologically active in vitro (antitumoral, antibacterial and DNA cleavage activities), showing better DNA cleavage in pH 6,5 at 50° C. These two complexes exhibit hydrogen bonding through the amide groups. The bis-triazenes [(R)ArNNN(H)(CH2)4N(H)NNAr(R)] 11 (R = H) and 15 (R = 2-C(O)NH2) are rotamers as showed in the 1H and 13C NMR spectra. The bis-triazene 11 shows interesting property in promoting the formation of binuclear complexes of Cu(II) (12), Ni(II) (13) and Pd(II) (14) with very short M−M distances and really strong M···M interactions. The Cu(II) complex (12) shows antiferromagnetism due to the strong Cu−Cu antiferromagnetic coupling. The three complexes (12, 13 and 14) exhibit intramolecular C−H···M anagostic interactions and intermolecular C−H···Ph interactions promoting supramolecular arrangement in the solid state. The copper tetrazenide complex 16 was synthesized from the reaction of the 2-amidephenylazide with Cu(OAc)2·H2O in EtOH in the presence of KOH and exemplifies a stable polimeric salt of potassium with the deprotonated amide group. A reaction mechanism of formation of the complex 16 is proposed. It is supposed , that the oxidation state of the Cu is +3, based on the square planar geometry of the copper, short Cu−N bond distances, different bond distances N−N in the tetrazenido chain (N−N=N−N), and diamagnetism. However, XANES and EXAFS should confirm it. The tripodal tris-triazene 17 is the first completely characterized of this class of molecule including the X-ray diffraction on single crystal analysis. Depending on the crystallization conditions, the crystal structures of 17 show a water or a DMSO molecule inside the cavity formed by the three triazene chains, depending on the crystallization conditions. The tristriazenide gives a trinuclear complex of Cu(II) (18) with two ligands double deprotonated. This complex is paramagnetic. The complexes 19 (M = Cu(I)) and 20 (M = Ag(I)) have similar structure to each other, being salts where the anionic part is composed by two ligands tris-triazenides completely deprotonated surrounding a cluster of the M5 type, while the cationic part is composed by the M+(PPh3)3OH2 fragment. |
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2023-03-17T13:12:42Z2023-03-17T13:12:42Z2013-01-31http://repositorio.ufsm.br/handle/1/28257Multi-nitrogenated ligands are versatile coordinating ligands to the transition metals. In this work, mono- and bis-triazenes, a tris-triazene, a tetrazenide and twelve metal complexes were synthesized, including the metal ions Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) and Cu(III). The triazenes and complexes were characterized by different analysis: infrared and UV-Vis spectroscopy, 1H, 13C and 31P NMR spectroscopy, low or high resolution mass spectrometry (EI, ESI, ESI(+)-TOF and ESI(-)-TOF) and X-ray diffraction on single crystal. The Cu(II) complex of the mono-triazenide N-oxide ligand [(2-Ph)ArNNN(®O)CH3]- (2) shows cis geometry on the coordinated center and possesses intramolecular Cu(II)···arene- interactions. Four complexes [(R’)ArNNNAr(R’’)Au(I)PPh3] were synthesized: 4 (R’ = OCH3, R’’ = 2-Ph), 6 (R’ = R’’ = 2-Ph), 8 (R’ = R’’ = 4-C(O)NH2) e 10 (R’ = 2-F, R’’ = 4-C(O)NH2). The crystal structure of 6 shows intramolecular Au(I)···arene- interaction. The complexes 8 and 10 are biologically active in vitro (antitumoral, antibacterial and DNA cleavage activities), showing better DNA cleavage in pH 6,5 at 50° C. These two complexes exhibit hydrogen bonding through the amide groups. The bis-triazenes [(R)ArNNN(H)(CH2)4N(H)NNAr(R)] 11 (R = H) and 15 (R = 2-C(O)NH2) are rotamers as showed in the 1H and 13C NMR spectra. The bis-triazene 11 shows interesting property in promoting the formation of binuclear complexes of Cu(II) (12), Ni(II) (13) and Pd(II) (14) with very short M−M distances and really strong M···M interactions. The Cu(II) complex (12) shows antiferromagnetism due to the strong Cu−Cu antiferromagnetic coupling. The three complexes (12, 13 and 14) exhibit intramolecular C−H···M anagostic interactions and intermolecular C−H···Ph interactions promoting supramolecular arrangement in the solid state. The copper tetrazenide complex 16 was synthesized from the reaction of the 2-amidephenylazide with Cu(OAc)2·H2O in EtOH in the presence of KOH and exemplifies a stable polimeric salt of potassium with the deprotonated amide group. A reaction mechanism of formation of the complex 16 is proposed. It is supposed , that the oxidation state of the Cu is +3, based on the square planar geometry of the copper, short Cu−N bond distances, different bond distances N−N in the tetrazenido chain (N−N=N−N), and diamagnetism. However, XANES and EXAFS should confirm it. The tripodal tris-triazene 17 is the first completely characterized of this class of molecule including the X-ray diffraction on single crystal analysis. Depending on the crystallization conditions, the crystal structures of 17 show a water or a DMSO molecule inside the cavity formed by the three triazene chains, depending on the crystallization conditions. The tristriazenide gives a trinuclear complex of Cu(II) (18) with two ligands double deprotonated. This complex is paramagnetic. The complexes 19 (M = Cu(I)) and 20 (M = Ag(I)) have similar structure to each other, being salts where the anionic part is composed by two ligands tris-triazenides completely deprotonated surrounding a cluster of the M5 type, while the cationic part is composed by the M+(PPh3)3OH2 fragment.Ligantes multi-nitrogenados possuem versatilidade para coordenação a metais de transição. Neste trabalho, foram sintetizados mono- e bis-triazenos, um tris-triazeno, um tetrazenido e doze complexos metálicos com os íons metálicos Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) e Cu(III). Os triazenos e complexos foram caracterizados por espectroscopia de IV e UV-Vis, espectroscopia de RMN 1H, 13C e 31P, espectrometria de massas de baixa ou alta resolução (EI, ESI, ESI(+)-TOF e ESI(- )-TOF) e difração de raios X em monocristal. O complexo de Cu(II) com o ligante mono-triazenido Nóxido [(2-Ph)ArNNN(®O)CH3]- (2) apresenta-se com geometria cis no centro de coordenação e possui interação Cu(II)···areno- intramolecular. Quatro complexos [(R’)ArNNNAr(R’’)Au(I)PPh3] foram sintetizados: 4 (R’ = OCH3, R’’ = 2-Ph), 6 (R’ = R’’ = 2-Ph), 8 (R’ = R’’ = 4-C(O)NH2) e 10 (R’ = 2-F, R’’ = 4-C(O)NH2). A estrutura cristalina do complexo 6 mostra interação do tipo Au(I)···areno- intramolecular. Os complexos 8 e 10 são biologicamente ativos in vitro (atividades antitumoral, antibacteriana e de clivagem do DNA), mostrando melhor atividade de clivagem do DNA em pH 6,5 a 50° C. Estes dois complexos apresentam grande número de ligações de hidrogênio através dos grupos amida. Os bis-triazenos [(R)ArNNN(H)(CH2)4N(H)NNAr(R)] 11 (R = H) e 15 (R = 2- C(O)NH2) apresentam-se na forma de isômeros de rotação como mostra a espectroscopia de RMN 1H e 13C. O bis-triazeno 11 possui interessante propriedade de formar complexos binucleares de Cu(II) (12), Ni(II) (13) e Pd(II) (14) com curtas distâncias M−M e interações M···M. O complexo de Cu(II) (12) possui antiferromagnetismo devido ao forte acoplamento antiferromagnético Cu−Cu. Os três complexos (12, 13 e 14) formam interações anagósticas intramoleculares do tipo C−H···M e interações intermoleculares do tipo C−H···Ph. O complexo tetrazenido de cobre (16) foi sintetizado a partir da reação da 2-amidofenilazida com Cu(OAc)2·H2O em EtOH na presenta de KOH e apresenta-se na forma de um sal polimérico estável de potássio como o grupo amida desprotonado. Um mecanismo de formação do complexo 16 é proposto. Através da geometria de coordenação quadrática do cobre, das curtas distâncias de ligações Cu−N, das distâncias de ligação na cadeia tetrazenido, da susceptibilidade magnética, pode-se supor que o estado de oxidação do Cu é +3. Contudo, análises de XANES e EXAFS deveriam confirmar isto. O tris-triazeno (N(2-PhN(H)NNPh)3) 17 tripodal é o primeiro completamente caracterizado, incluindo a estrutura cristalina determinada por difração de raios X e inclui uma molécula de água ou de DMSO na cavidade formada pelas três cadeias triazeno, dependendo das condições de cristalização. O tris-triazenido forma o complexo de Cu(II) trinuclear (18) com dois ligantes duplamente desprotonados. Este complexo é paramagnético. Os complexos 19 (M = Cu(I)) e 20 (M = Ag(I)) possuem estruturas similares entre si, sendo sais nos quais a parte aniônica é composta por dois ligantes tris-triazenidos completamente desprotonados envolvendo um cluster do tipo M5 e, a parte catiônica possui o fragmento [M(PPh3)3(OH2)]+.porUniversidade 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/openAccessMono-triazenoBis-triazenoTris-triazeno tripodalTriazeno N-óxidoTetrazenoComplexosCu(I)Ag(I)Au(I)Cu(II)Ni(II)Pd(II)Cu(III)Susceptibilidade magnéticaEstrutura cristalinaAtividades antitumoralAntibacteriana e de clivagem do DNA in vitroQuímica supramolecularMono-triazeneBis-triazeneTripodal tris-triazeneTriazene N-oxideTetrazenideComplexesMagnetic susceptibilityCrystal structureIn vitro antitumoralAntibacterial and DNA cleavage activitiesSupramolecular chemistryCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAMono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitroMono-, bis- and tris-triazenes, tetrazene and complexes of Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) AND Cu(III): synthesis, characterization, crystal structure, in vitro antitumoral, antibacterial and DNA cleavege activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisHorner, Manfredohttp://lattes.cnpq.br/8922528250830998Beck, JohannesNunes, Fábio SouzaSantos, Aline Joana Rolina Wohlmuth Alves dosBack, Davi FernandoFenner, Hertonhttp://lattes.cnpq.br/3613798169666494Paraginski, Gustavo Luiz1006000000006006006006006006006006005997bd94-cd6e-43ac-8db1-93b1f40cc684b244639b-72cf-4b1f-b302-b49cde1ae739f5d8e788-987d-4c9b-afa7-61434debc24049aef824-0b66-45ed-8f19-27f9c948e5c5370d59b8-d373-4deb-9625-94b7619a97eaa47fce89-23ee-429f-8ccf-d3fa1be2829fc032f384-d82f-4f78-a069-dcf4471c7f5dreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
dc.title.alternative.eng.fl_str_mv |
Mono-, bis- and tris-triazenes, tetrazene and complexes of Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) AND Cu(III): synthesis, characterization, crystal structure, in vitro antitumoral, antibacterial and DNA cleavege activities |
title |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
spellingShingle |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro Paraginski, Gustavo Luiz Mono-triazeno Bis-triazeno Tris-triazeno tripodal Triazeno N-óxido Tetrazeno Complexos Cu(I) Ag(I) Au(I) Cu(II) Ni(II) Pd(II) Cu(III) Susceptibilidade magnética Estrutura cristalina Atividades antitumoral Antibacteriana e de clivagem do DNA in vitro Química supramolecular Mono-triazene Bis-triazene Tripodal tris-triazene Triazene N-oxide Tetrazenide Complexes Magnetic susceptibility Crystal structure In vitro antitumoral Antibacterial and DNA cleavage activities Supramolecular chemistry CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
title_full |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
title_fullStr |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
title_full_unstemmed |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
title_sort |
Mono-, bis- e tris-triazenos, tetrazeno e complexos de Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) E Cu(III): síntese, caracterização, estrutura cristalina, atividades antitumoral, antibacteriana e de clivagem do DNA in vitro |
author |
Paraginski, Gustavo Luiz |
author_facet |
Paraginski, Gustavo Luiz |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Horner, Manfredo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/8922528250830998 |
dc.contributor.advisor-co1.fl_str_mv |
Beck, Johannes |
dc.contributor.referee1.fl_str_mv |
Nunes, Fábio Souza |
dc.contributor.referee2.fl_str_mv |
Santos, Aline Joana Rolina Wohlmuth Alves dos |
dc.contributor.referee3.fl_str_mv |
Back, Davi Fernando |
dc.contributor.referee4.fl_str_mv |
Fenner, Herton |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3613798169666494 |
dc.contributor.author.fl_str_mv |
Paraginski, Gustavo Luiz |
contributor_str_mv |
Horner, Manfredo Beck, Johannes Nunes, Fábio Souza Santos, Aline Joana Rolina Wohlmuth Alves dos Back, Davi Fernando Fenner, Herton |
dc.subject.por.fl_str_mv |
Mono-triazeno Bis-triazeno Tris-triazeno tripodal Triazeno N-óxido Tetrazeno Complexos Cu(I) Ag(I) Au(I) Cu(II) Ni(II) Pd(II) Cu(III) Susceptibilidade magnética Estrutura cristalina Atividades antitumoral Antibacteriana e de clivagem do DNA in vitro |
topic |
Mono-triazeno Bis-triazeno Tris-triazeno tripodal Triazeno N-óxido Tetrazeno Complexos Cu(I) Ag(I) Au(I) Cu(II) Ni(II) Pd(II) Cu(III) Susceptibilidade magnética Estrutura cristalina Atividades antitumoral Antibacteriana e de clivagem do DNA in vitro Química supramolecular Mono-triazene Bis-triazene Tripodal tris-triazene Triazene N-oxide Tetrazenide Complexes Magnetic susceptibility Crystal structure In vitro antitumoral Antibacterial and DNA cleavage activities Supramolecular chemistry CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Química supramolecular Mono-triazene Bis-triazene Tripodal tris-triazene Triazene N-oxide Tetrazenide Complexes Magnetic susceptibility Crystal structure In vitro antitumoral Antibacterial and DNA cleavage activities Supramolecular chemistry |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Multi-nitrogenated ligands are versatile coordinating ligands to the transition metals. In this work, mono- and bis-triazenes, a tris-triazene, a tetrazenide and twelve metal complexes were synthesized, including the metal ions Cu(I), Ag(I), Au(I), Cu(II), Ni(II), Pd(II) and Cu(III). The triazenes and complexes were characterized by different analysis: infrared and UV-Vis spectroscopy, 1H, 13C and 31P NMR spectroscopy, low or high resolution mass spectrometry (EI, ESI, ESI(+)-TOF and ESI(-)-TOF) and X-ray diffraction on single crystal. The Cu(II) complex of the mono-triazenide N-oxide ligand [(2-Ph)ArNNN(®O)CH3]- (2) shows cis geometry on the coordinated center and possesses intramolecular Cu(II)···arene- interactions. Four complexes [(R’)ArNNNAr(R’’)Au(I)PPh3] were synthesized: 4 (R’ = OCH3, R’’ = 2-Ph), 6 (R’ = R’’ = 2-Ph), 8 (R’ = R’’ = 4-C(O)NH2) e 10 (R’ = 2-F, R’’ = 4-C(O)NH2). The crystal structure of 6 shows intramolecular Au(I)···arene- interaction. The complexes 8 and 10 are biologically active in vitro (antitumoral, antibacterial and DNA cleavage activities), showing better DNA cleavage in pH 6,5 at 50° C. These two complexes exhibit hydrogen bonding through the amide groups. The bis-triazenes [(R)ArNNN(H)(CH2)4N(H)NNAr(R)] 11 (R = H) and 15 (R = 2-C(O)NH2) are rotamers as showed in the 1H and 13C NMR spectra. The bis-triazene 11 shows interesting property in promoting the formation of binuclear complexes of Cu(II) (12), Ni(II) (13) and Pd(II) (14) with very short M−M distances and really strong M···M interactions. The Cu(II) complex (12) shows antiferromagnetism due to the strong Cu−Cu antiferromagnetic coupling. The three complexes (12, 13 and 14) exhibit intramolecular C−H···M anagostic interactions and intermolecular C−H···Ph interactions promoting supramolecular arrangement in the solid state. The copper tetrazenide complex 16 was synthesized from the reaction of the 2-amidephenylazide with Cu(OAc)2·H2O in EtOH in the presence of KOH and exemplifies a stable polimeric salt of potassium with the deprotonated amide group. A reaction mechanism of formation of the complex 16 is proposed. It is supposed , that the oxidation state of the Cu is +3, based on the square planar geometry of the copper, short Cu−N bond distances, different bond distances N−N in the tetrazenido chain (N−N=N−N), and diamagnetism. However, XANES and EXAFS should confirm it. The tripodal tris-triazene 17 is the first completely characterized of this class of molecule including the X-ray diffraction on single crystal analysis. Depending on the crystallization conditions, the crystal structures of 17 show a water or a DMSO molecule inside the cavity formed by the three triazene chains, depending on the crystallization conditions. The tristriazenide gives a trinuclear complex of Cu(II) (18) with two ligands double deprotonated. This complex is paramagnetic. The complexes 19 (M = Cu(I)) and 20 (M = Ag(I)) have similar structure to each other, being salts where the anionic part is composed by two ligands tris-triazenides completely deprotonated surrounding a cluster of the M5 type, while the cationic part is composed by the M+(PPh3)3OH2 fragment. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-01-31 |
dc.date.accessioned.fl_str_mv |
2023-03-17T13:12:42Z |
dc.date.available.fl_str_mv |
2023-03-17T13:12:42Z |
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/1/28257 |
url |
http://repositorio.ufsm.br/handle/1/28257 |
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 |
5997bd94-cd6e-43ac-8db1-93b1f40cc684 b244639b-72cf-4b1f-b302-b49cde1ae739 f5d8e788-987d-4c9b-afa7-61434debc240 49aef824-0b66-45ed-8f19-27f9c948e5c5 370d59b8-d373-4deb-9625-94b7619a97ea a47fce89-23ee-429f-8ccf-d3fa1be2829f c032f384-d82f-4f78-a069-dcf4471c7f5d |
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/1/28257/2/license_rdf http://repositorio.ufsm.br/bitstream/1/28257/3/license.txt http://repositorio.ufsm.br/bitstream/1/28257/1/TES_PPGQU%c3%8dMICA_2013_PARAGINSKI_GUSTAVO.pdf |
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Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
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|
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1794524325109301248 |