Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada
Ano de defesa: | 2015 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
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/1/28213 |
Resumo: | This work reports the synthesis of new [2]rotaxanes, [2]-[1,2-bis(aminocarbonyl- (1'-(1',1'-dimethylethyl)-1H-pyrazol-3'-yl))-ethane]-rotaxa-1,7,14,20-tetraaza- 2,6,15,19-tetraoxo-3,5,912,16,18,22,25-tetrabenzocicloexacosano], by fivecomponent clipping reaction, derived from isomers 1,3- and 1,5-pyrazoles, such as bulky groups in the thread. Firstly, performed the synthesis of pyrazoles using the ketoesters ([EtO2CC(O)C=C(R)OMe, where R =Me, Pr, Ph, p-F-Ph, p- Cl-Ph e p-Br-Ph] with N-tert-butilhidrazine hydrochloride and pyridine as base, furnished a series of 1,3-pyrazoles ethyl 1-(1,1-dimethylethyl)-1H-pyrazol-3- carboxylate in 69-81% of yields. For 1,5-pyrazoles, ethyl 1-(1,1-dimethylethyl)- 1H-pyrazol-5-carboxylate were use the same reagents for the synthesis of 1,3- pyrazoles, but using KOH as base. The yields for these compounds were 78- 88%. Hydrolysis was performed at the ester grouping pyrazoles with NaOH for the two isomers series, forming products acids1,3-pyrazoles (75-92%) and 1,5- pyrazoles (92-98%). This step is necessary because they are very important to obtain new threads. For the synthesis of threads were used the acids pyrazoles (1,3- and 1,5-isomers), reacting it with triphenyl phosphite, pyridine and ethylene diamine, with yield of 69-95% and 70-90% respectively. Pyrazoles were used as bulky groups in the threads to determine the effect of the substituent pyrazole in the formation of the new [2]rotaxanes. The synthesis of [2]rotaxanes were carried out with the threads, isophthaloyl dichloride, pxylylene diamine and triethylamine. Only the 1,3-threads formed [2]rotaxanes (7-19%). To study the stability of molecular subcomponents was used high temperatures in DMSO in two periods of time. It was observed that the molecular subcomponents were stable, because not having a total breakdown of the structure. Also, the NMR experiments were carried out using T1 experiments for threads and [2]rotaxanes, noting that with the increase in structure, smaller T1 values were obtained. |
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2023-03-15T15:29:58Z2023-03-15T15:29:58Z2015-02-25http://repositorio.ufsm.br/handle/1/28213This work reports the synthesis of new [2]rotaxanes, [2]-[1,2-bis(aminocarbonyl- (1'-(1',1'-dimethylethyl)-1H-pyrazol-3'-yl))-ethane]-rotaxa-1,7,14,20-tetraaza- 2,6,15,19-tetraoxo-3,5,912,16,18,22,25-tetrabenzocicloexacosano], by fivecomponent clipping reaction, derived from isomers 1,3- and 1,5-pyrazoles, such as bulky groups in the thread. Firstly, performed the synthesis of pyrazoles using the ketoesters ([EtO2CC(O)C=C(R)OMe, where R =Me, Pr, Ph, p-F-Ph, p- Cl-Ph e p-Br-Ph] with N-tert-butilhidrazine hydrochloride and pyridine as base, furnished a series of 1,3-pyrazoles ethyl 1-(1,1-dimethylethyl)-1H-pyrazol-3- carboxylate in 69-81% of yields. For 1,5-pyrazoles, ethyl 1-(1,1-dimethylethyl)- 1H-pyrazol-5-carboxylate were use the same reagents for the synthesis of 1,3- pyrazoles, but using KOH as base. The yields for these compounds were 78- 88%. Hydrolysis was performed at the ester grouping pyrazoles with NaOH for the two isomers series, forming products acids1,3-pyrazoles (75-92%) and 1,5- pyrazoles (92-98%). This step is necessary because they are very important to obtain new threads. For the synthesis of threads were used the acids pyrazoles (1,3- and 1,5-isomers), reacting it with triphenyl phosphite, pyridine and ethylene diamine, with yield of 69-95% and 70-90% respectively. Pyrazoles were used as bulky groups in the threads to determine the effect of the substituent pyrazole in the formation of the new [2]rotaxanes. The synthesis of [2]rotaxanes were carried out with the threads, isophthaloyl dichloride, pxylylene diamine and triethylamine. Only the 1,3-threads formed [2]rotaxanes (7-19%). To study the stability of molecular subcomponents was used high temperatures in DMSO in two periods of time. It was observed that the molecular subcomponents were stable, because not having a total breakdown of the structure. Also, the NMR experiments were carried out using T1 experiments for threads and [2]rotaxanes, noting that with the increase in structure, smaller T1 values were obtained.Este trabalho descreve a síntese de novos [2]rotaxanos [2]-[1,2- Bis(aminocarbonil-(1'-(1',1'-dimetiletil)-1H-pirazol-3'-il))-etano]-rotaxa-1,7,14,20- tetraaza-2,6,15,19-tetraoxo-3,5,9,12,16,18,22,25-tetrabenzociclo-exacosano] pela reação de cinco componentes utilizando o método Clipping, a partir de derivados dos isômeros pirazóis-1,3 e -1,5, como grupamentos volumosos nos filamentos lineares. Primeiramente, foi realizado a síntese dos pirazóis utilizando ceto-ésteres ([EtO2CC(O)C=C(R)OMe, onde R =Me, Pr, Ph, p-F-Ph, p-Cl-Ph e p-Br-Ph], cloridrato de t-butilhidrazina e piridina como base, fornecendo a série de pirazóis-1,3 1-(1,1-dimetiletil)-1H-pirazol-3-carboxilato de etila em 69-81% de rendimento. Para os pirazóis-1,5, 1-(1,1-dimetiletil)-1Hpirazol- 5-carboxilato de etila, foi utilizado os mesmos precursores para a síntese dos pirazóis-1,3, mas utilizando KOH como base. Os rendimentos para estes compostos foram de 78-88%. Realizou-se a hidrólise do grupamento éster dos pirazóis com NaOH, para as duas séries de isômeros, formando produtos com rendimento de 75-92% para os ácidos 1,3-pirazóis e 92-98% para os 1,5-pirazóis. Essa etapa é necessária pois os mesmos são de suma importância para se obter os novos filamentos lineares. Para a síntese dos filamentos lineares, foi utilizado tanto os ácidos de pirazóis do isômero-1,3 quanto o isômero-1,5, reagindo-os com trifenil fosfito, piridina e etilenodiamina,com rendimento de 69-95% e 70-90% respectivamente. Os pirazóis foram utilizados como grupamentos volumosos nos filamentos lineares, para verificar o efeito do substituinte do pirazol na formação dos novos [2]rotaxanos. Para a síntese dos [2]rotaxanos foram utilizados os filamentos lineares, dicloreto de benzoíla, a p-xililenodiamina e trietilamina. Verificou-se que somente os filamentos lineares, provenientes do isômero-1,3, formaram os [2]rotaxanos com rendimentos de 7-19%. Para o estudo da estabilidade dos subcomponentes moleculares foi utilizado altas temperaturas em DMSO, em dois períodos de tempos. Foi observado que os subcomponentes moleculares se mostraram estáveis, devido não apresentarem um desmembramento total da estrutura. Também, foi realizado o estudo de RMN, utilizando os experimentos de T1 para os filamentos lineares e [2]rotaxanos, observando que com o aumento da estrutura, menores valores de T1 foram obtidos.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/openAccessPirazóisMoléculas mecanicamente entrelaçadas[2]rotaxanosPyrazolesMechanically interlocked molecules[2] RotaxanesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçadaSynthesis of [2]rotaxanes: relationship between pyrazoles structure linked to thread and formation interlocked moleculesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Frizzo, Clarissa PiccininBonacorso, Helio GauzeFavaro, Denize Cristinahttp://lattes.cnpq.br/1658070623105213Zimmer, Geórgia Cristiane100600000000600600600600600600c28419d9-6027-4f9c-acd2-76e8067a85d15efa3199-292b-4c30-afbf-28f1977824bdd547141e-3d22-4b07-ad8d-c6e60d6d1dd9dbcce58b-96b0-4f45-a78d-ca6f339e038d177bae64-f3cc-42a2-9c97-88d95fbc8cf9reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2015_ZIMMER_GEORGIA.pdfDIS_PPGQUIMICA_2015_ZIMMER_GEORGIA.pdfDissertação de mestradoapplication/pdf47079674http://repositorio.ufsm.br/bitstream/1/28213/1/DIS_PPGQUIMICA_2015_ZIMMER_GEORGIA.pdf6e3e1dfcb8222e118069b485a2f9f2a1MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/28213/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/28213/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/282132023-03-15 12:29:58.462oai:repositorio.ufsm.br:1/28213TElDRU7Dh0EgREUgRElTVFJJQlVJw4fDg08gTsODTy1FWENMVVNJVkEKCkNvbSBhIGFwcmVzZW50YcOnw6NvIGRlc3RhIGxpY2Vuw6dhLCB2b2PDqiAobyBhdXRvciAoZXMpIG91IG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgZGUgYXV0b3IpIGNvbmNlZGUgw6AgVW5pdmVyc2lkYWRlCkZlZGVyYWwgZGUgU2FudGEgTWFyaWEgKFVGU00pIG8gZGlyZWl0byBuw6NvLWV4Y2x1c2l2byBkZSByZXByb2R1emlyLCAgdHJhZHV6aXIgKGNvbmZvcm1lIGRlZmluaWRvIGFiYWl4byksIGUvb3UKZGlzdHJpYnVpciBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gKGluY2x1aW5kbyBvIHJlc3VtbykgcG9yIHRvZG8gbyBtdW5kbyBubyBmb3JtYXRvIGltcHJlc3NvIGUgZWxldHLDtG5pY28gZQplbSBxdWFscXVlciBtZWlvLCBpbmNsdWluZG8gb3MgZm9ybWF0b3Mgw6F1ZGlvIG91IHbDrWRlby4KClZvY8OqIGNvbmNvcmRhIHF1ZSBhIFVGU00gcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250ZcO6ZG8sIHRyYW5zcG9yIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbwpwYXJhIHF1YWxxdWVyIG1laW8gb3UgZm9ybWF0byBwYXJhIGZpbnMgZGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIHRhbWLDqW0gY29uY29yZGEgcXVlIGEgVUZTTSBwb2RlIG1hbnRlciBtYWlzIGRlIHVtYSBjw7NwaWEgYSBzdWEgdGVzZSBvdQpkaXNzZXJ0YcOnw6NvIHBhcmEgZmlucyBkZSBzZWd1cmFuw6dhLCBiYWNrLXVwIGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIGRlY2xhcmEgcXVlIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyDDqSBvcmlnaW5hbCBlIHF1ZSB2b2PDqiB0ZW0gbyBwb2RlciBkZSBjb25jZWRlciBvcyBkaXJlaXRvcyBjb250aWRvcwpuZXN0YSBsaWNlbsOnYS4gVm9jw6ogdGFtYsOpbSBkZWNsYXJhIHF1ZSBvIGRlcMOzc2l0byBkYSBzdWEgdGVzZSBvdSBkaXNzZXJ0YcOnw6NvIG7Do28sIHF1ZSBzZWphIGRlIHNldQpjb25oZWNpbWVudG8sIGluZnJpbmdlIGRpcmVpdG9zIGF1dG9yYWlzIGRlIG5pbmd1w6ltLgoKQ2FzbyBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gY29udGVuaGEgbWF0ZXJpYWwgcXVlIHZvY8OqIG7Do28gcG9zc3VpIGEgdGl0dWxhcmlkYWRlIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgdm9jw6oKZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc8OjbyBpcnJlc3RyaXRhIGRvIGRldGVudG9yIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBwYXJhIGNvbmNlZGVyIMOgIFVGU00Kb3MgZGlyZWl0b3MgYXByZXNlbnRhZG9zIG5lc3RhIGxpY2Vuw6dhLCBlIHF1ZSBlc3NlIG1hdGVyaWFsIGRlIHByb3ByaWVkYWRlIGRlIHRlcmNlaXJvcyBlc3TDoSBjbGFyYW1lbnRlCmlkZW50aWZpY2FkbyBlIHJlY29uaGVjaWRvIG5vIHRleHRvIG91IG5vIGNvbnRlw7pkbyBkYSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gb3JhIGRlcG9zaXRhZGEuCgpDQVNPIEEgVEVTRSBPVSBESVNTRVJUQcOHw4NPIE9SQSBERVBPU0lUQURBIFRFTkhBIFNJRE8gUkVTVUxUQURPIERFIFVNIFBBVFJPQ8ONTklPIE9VCkFQT0lPIERFIFVNQSBBR8OKTkNJQSBERSBGT01FTlRPIE9VIE9VVFJPIE9SR0FOSVNNTyBRVUUgTsODTyBTRUpBIEEgVUZTTQosIFZPQ8OKIERFQ0xBUkEgUVVFIFJFU1BFSVRPVSBUT0RPUyBFIFFVQUlTUVVFUiBESVJFSVRPUyBERSBSRVZJU8ODTyBDT01PClRBTULDiU0gQVMgREVNQUlTIE9CUklHQcOHw5VFUyBFWElHSURBUyBQT1IgQ09OVFJBVE8gT1UgQUNPUkRPLgoKQSBVRlNNIHNlIGNvbXByb21ldGUgYSBpZGVudGlmaWNhciBjbGFyYW1lbnRlIG8gc2V1IG5vbWUgKHMpIG91IG8ocykgbm9tZShzKSBkbyhzKQpkZXRlbnRvcihlcykgZG9zIGRpcmVpdG9zIGF1dG9yYWlzIGRhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbywgZSBuw6NvIGZhcsOhIHF1YWxxdWVyIGFsdGVyYcOnw6NvLCBhbMOpbSBkYXF1ZWxhcwpjb25jZWRpZGFzIHBvciBlc3RhIGxpY2Vuw6dhLgoKRepositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132023-03-15T15:29:58Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
dc.title.alternative.eng.fl_str_mv |
Synthesis of [2]rotaxanes: relationship between pyrazoles structure linked to thread and formation interlocked molecules |
title |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
spellingShingle |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada Zimmer, Geórgia Cristiane Pirazóis Moléculas mecanicamente entrelaçadas [2]rotaxanos Pyrazoles Mechanically interlocked molecules [2] Rotaxanes CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
title_full |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
title_fullStr |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
title_full_unstemmed |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
title_sort |
Síntese de [2]rotaxanos: relação entre a estrutura de pirazóis ligados ao filamento linear e a formação da molécula entrelaçada |
author |
Zimmer, Geórgia Cristiane |
author_facet |
Zimmer, Geórgia Cristiane |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.advisor-co1.fl_str_mv |
Frizzo, Clarissa Piccinin |
dc.contributor.referee1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee2.fl_str_mv |
Favaro, Denize Cristina |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1658070623105213 |
dc.contributor.author.fl_str_mv |
Zimmer, Geórgia Cristiane |
contributor_str_mv |
Martins, Marcos Antonio Pinto Frizzo, Clarissa Piccinin Bonacorso, Helio Gauze Favaro, Denize Cristina |
dc.subject.por.fl_str_mv |
Pirazóis Moléculas mecanicamente entrelaçadas [2]rotaxanos |
topic |
Pirazóis Moléculas mecanicamente entrelaçadas [2]rotaxanos Pyrazoles Mechanically interlocked molecules [2] Rotaxanes CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Pyrazoles Mechanically interlocked molecules [2] Rotaxanes |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work reports the synthesis of new [2]rotaxanes, [2]-[1,2-bis(aminocarbonyl- (1'-(1',1'-dimethylethyl)-1H-pyrazol-3'-yl))-ethane]-rotaxa-1,7,14,20-tetraaza- 2,6,15,19-tetraoxo-3,5,912,16,18,22,25-tetrabenzocicloexacosano], by fivecomponent clipping reaction, derived from isomers 1,3- and 1,5-pyrazoles, such as bulky groups in the thread. Firstly, performed the synthesis of pyrazoles using the ketoesters ([EtO2CC(O)C=C(R)OMe, where R =Me, Pr, Ph, p-F-Ph, p- Cl-Ph e p-Br-Ph] with N-tert-butilhidrazine hydrochloride and pyridine as base, furnished a series of 1,3-pyrazoles ethyl 1-(1,1-dimethylethyl)-1H-pyrazol-3- carboxylate in 69-81% of yields. For 1,5-pyrazoles, ethyl 1-(1,1-dimethylethyl)- 1H-pyrazol-5-carboxylate were use the same reagents for the synthesis of 1,3- pyrazoles, but using KOH as base. The yields for these compounds were 78- 88%. Hydrolysis was performed at the ester grouping pyrazoles with NaOH for the two isomers series, forming products acids1,3-pyrazoles (75-92%) and 1,5- pyrazoles (92-98%). This step is necessary because they are very important to obtain new threads. For the synthesis of threads were used the acids pyrazoles (1,3- and 1,5-isomers), reacting it with triphenyl phosphite, pyridine and ethylene diamine, with yield of 69-95% and 70-90% respectively. Pyrazoles were used as bulky groups in the threads to determine the effect of the substituent pyrazole in the formation of the new [2]rotaxanes. The synthesis of [2]rotaxanes were carried out with the threads, isophthaloyl dichloride, pxylylene diamine and triethylamine. Only the 1,3-threads formed [2]rotaxanes (7-19%). To study the stability of molecular subcomponents was used high temperatures in DMSO in two periods of time. It was observed that the molecular subcomponents were stable, because not having a total breakdown of the structure. Also, the NMR experiments were carried out using T1 experiments for threads and [2]rotaxanes, noting that with the increase in structure, smaller T1 values were obtained. |
publishDate |
2015 |
dc.date.issued.fl_str_mv |
2015-02-25 |
dc.date.accessioned.fl_str_mv |
2023-03-15T15:29:58Z |
dc.date.available.fl_str_mv |
2023-03-15T15:29:58Z |
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/1/28213 |
url |
http://repositorio.ufsm.br/handle/1/28213 |
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 |
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:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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Universidade Federal de Santa Maria (UFSM) |
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Manancial - Repositório Digital da UFSM |
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