Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona
Ano de defesa: | 2013 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | eng |
Instituição de defesa: |
Não Informado pela instituição
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Programa de Pós-Graduação: |
Pós-Graduação em Química
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Departamento: |
Não Informado pela instituição
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País: |
Não Informado pela instituição
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Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | https://ri.ufs.br/handle/riufs/6139 |
Resumo: | The hydrochloric acid catalyzed reaction of 1-tetralone (10 mmol) and thiosemicarbazide (10 mmol) in a 3:1 mixture of ethanol and water (100 ml) was refluxed for 7 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained by recrystallization from tetrahydrofurane. The molecular structure of the tetralone-thiosemicarbazone, C11H13N3S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) A for an aliphatic C atom, which corresponds to an envelope conformation for the nonaromatic ring. The thiosemicarbazone moiety and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) A, respectively, and the dihedral angle between the two planes is 8.84 (13)o. In the crystal, molecules are linked into chains by pairs of N-H¡E¡E¡ES hydrogen bonds along [1 -1 0], forming a one-dimensional H bonded polymer. The molecule shows an trans conformation for the atoms about the C1¡XN1/N1¡XN2/N2¡XC11 bonds. The cystal data are: space group monoclinic, C 2/c, a = 15.4388 (11) A, b = 5.5781 (3) A, c = 26.338 (2) A e Ò = 102.940 (6)o. Through 1H NMR spectrum was observed that the tautomeric thione form is predominant in solution. All starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously. This work is already published (Oliveira et al., Acta Cryst. (2012). E68, o2581). |
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Silva, Cecília Santoshttp://lattes.cnpq.br/0952404174788513Oliveira, Adriano Bof dehttp://lattes.cnpq.br/64881213390524882017-09-27T13:58:00Z2017-09-27T13:58:00Z2013-09-13https://ri.ufs.br/handle/riufs/6139The hydrochloric acid catalyzed reaction of 1-tetralone (10 mmol) and thiosemicarbazide (10 mmol) in a 3:1 mixture of ethanol and water (100 ml) was refluxed for 7 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained by recrystallization from tetrahydrofurane. The molecular structure of the tetralone-thiosemicarbazone, C11H13N3S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) A for an aliphatic C atom, which corresponds to an envelope conformation for the nonaromatic ring. The thiosemicarbazone moiety and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) A, respectively, and the dihedral angle between the two planes is 8.84 (13)o. In the crystal, molecules are linked into chains by pairs of N-H¡E¡E¡ES hydrogen bonds along [1 -1 0], forming a one-dimensional H bonded polymer. The molecule shows an trans conformation for the atoms about the C1¡XN1/N1¡XN2/N2¡XC11 bonds. The cystal data are: space group monoclinic, C 2/c, a = 15.4388 (11) A, b = 5.5781 (3) A, c = 26.338 (2) A e Ò = 102.940 (6)o. Through 1H NMR spectrum was observed that the tautomeric thione form is predominant in solution. All starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously. This work is already published (Oliveira et al., Acta Cryst. (2012). E68, o2581).A reação da 1-tetralona (10 mmol) com a tiossemicarbazida (10mmol) foi feita numa solucao etanol e agua, em proporcao 3:1, respectivamente. A solucao de 100 mL foi refluxada durante 7 h. Apos o resfriamento e filtracao, foram obtidos cristais adequados para a difracao de raios-X em monocristal. A estrutura molecular da tetralona-tiossemicarbazona e inedita, C11H13N3S, e nao e planar: o desvio maximo do plano principal que passa pelos atomos nao hidrogenoides e de 0,521(2) A para um carbono alifatico, o que esta de acordo com a conformacao de envelope do anel nao aromatico. O fragmento tiossemicarzona e o grupo contendo o anel aromatico apresentam desvios maximos do plano ideal atraves dos atomos nao hidrogenoides de 0,0288(16) e 0,0124(27) A, respectivamente e o angulo entre os planos e de 8,84 (13)o. No estado solido, as moleculas estao conectadas por pares de interacoes de hidrogenio centrossimetricas do tipo N-H¡E¡E¡ES na direcao cristalografica [1 -1 0], formando um polimero de ligacoes de hidrogenio unidimensional. Alem disso, a molecula possui uma conformacao trans em relacao as ligacoes quimicas C1¡XN1/N1¡XN2/N2¡XC11. O grupo espacial e monoclinico, C 2/c e as constantes de cela sao a = 15,4388 (11) A, b = 5,5781 (3) A, c = 26,338 (2) A e Ò = 102,940 (6)o. Atraves do espectro de RMN 1H foi observado que a forma tautomerica tiona e predominante em solucao. A sintese ja e conhecida na literatura e todos os edutos utilizados sao disponiveis comercialmente. Foram utilizados sem purificacao ou tratamento previos. Este trabalho ja esta publicado (Oliveira et al., Acta Cryst. (2012). E68, o2581).application/pdfengQuímicaTiossemicarbazonasEstrutura molecularTetralonaCompostos orgânicosChemistryMolecular structureOrganic compoundsTetraloneThiosemicarbazonesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICADeterminação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazonainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisPós-Graduação em Químicainfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSinstname:Universidade Federal de Sergipe (UFS)instacron:UFSORIGINALCECILIA_SANTOS_SILVA.pdfapplication/pdf2745613https://ri.ufs.br/jspui/bitstream/riufs/6139/1/CECILIA_SANTOS_SILVA.pdf2e546371c2422f7fb7be0e33ca55000fMD51TEXTCECILIA_SANTOS_SILVA.pdf.txtCECILIA_SANTOS_SILVA.pdf.txtExtracted texttext/plain82594https://ri.ufs.br/jspui/bitstream/riufs/6139/2/CECILIA_SANTOS_SILVA.pdf.txtb92fcaeaf542356af6ddf3f42a23cb1fMD52THUMBNAILCECILIA_SANTOS_SILVA.pdf.jpgCECILIA_SANTOS_SILVA.pdf.jpgGenerated Thumbnailimage/jpeg1424https://ri.ufs.br/jspui/bitstream/riufs/6139/3/CECILIA_SANTOS_SILVA.pdf.jpg2c6f2f1b37c1fd6ac9995a4e9f74128eMD53riufs/61392018-01-16 19:39:17.553oai:ufs.br:riufs/6139Repositório InstitucionalPUBhttps://ri.ufs.br/oai/requestrepositorio@academico.ufs.bropendoar:2018-01-16T22:39:17Repositório Institucional da UFS - Universidade Federal de Sergipe (UFS)false |
dc.title.por.fl_str_mv |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
title |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
spellingShingle |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona Silva, Cecília Santos Química Tiossemicarbazonas Estrutura molecular Tetralona Compostos orgânicos Chemistry Molecular structure Organic compounds Tetralone Thiosemicarbazones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
title_full |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
title_fullStr |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
title_full_unstemmed |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
title_sort |
Determinação da estrutura cristalina/molecular de um derivado da tiossemicarbazona com atividade farmacológica, a tetralona-tiossemicarbazona |
author |
Silva, Cecília Santos |
author_facet |
Silva, Cecília Santos |
author_role |
author |
dc.contributor.author.fl_str_mv |
Silva, Cecília Santos |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0952404174788513 |
dc.contributor.advisor1.fl_str_mv |
Oliveira, Adriano Bof de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6488121339052488 |
contributor_str_mv |
Oliveira, Adriano Bof de |
dc.subject.eng.fl_str_mv |
Química Tiossemicarbazonas Estrutura molecular Tetralona Compostos orgânicos Chemistry Molecular structure Organic compounds Tetralone Thiosemicarbazones |
topic |
Química Tiossemicarbazonas Estrutura molecular Tetralona Compostos orgânicos Chemistry Molecular structure Organic compounds Tetralone Thiosemicarbazones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The hydrochloric acid catalyzed reaction of 1-tetralone (10 mmol) and thiosemicarbazide (10 mmol) in a 3:1 mixture of ethanol and water (100 ml) was refluxed for 7 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained by recrystallization from tetrahydrofurane. The molecular structure of the tetralone-thiosemicarbazone, C11H13N3S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) A for an aliphatic C atom, which corresponds to an envelope conformation for the nonaromatic ring. The thiosemicarbazone moiety and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) A, respectively, and the dihedral angle between the two planes is 8.84 (13)o. In the crystal, molecules are linked into chains by pairs of N-H¡E¡E¡ES hydrogen bonds along [1 -1 0], forming a one-dimensional H bonded polymer. The molecule shows an trans conformation for the atoms about the C1¡XN1/N1¡XN2/N2¡XC11 bonds. The cystal data are: space group monoclinic, C 2/c, a = 15.4388 (11) A, b = 5.5781 (3) A, c = 26.338 (2) A e Ò = 102.940 (6)o. Through 1H NMR spectrum was observed that the tautomeric thione form is predominant in solution. All starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously. This work is already published (Oliveira et al., Acta Cryst. (2012). E68, o2581). |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-09-13 |
dc.date.accessioned.fl_str_mv |
2017-09-27T13:58:00Z |
dc.date.available.fl_str_mv |
2017-09-27T13:58:00Z |
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 |
https://ri.ufs.br/handle/riufs/6139 |
url |
https://ri.ufs.br/handle/riufs/6139 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
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Pós-Graduação em Química |
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