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Please use this identifier to cite or link to this item: https://rima.ufrrj.br/jspui/handle/20.500.14407/10230
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dc.contributor.authorAlmeida, Paulo Afonso de
dc.date.accessioned2023-12-21T18:59:13Z-
dc.date.available2023-12-21T18:59:13Z-
dc.date.issued2004-03-12
dc.identifier.citationAlmeida, Paulo Afonso de. Mesoiônicos da Classe 1,3-Ditiólio-4-Tiolatos: síntese, reações de cicloadição 1,3-Dipolar e estudo do efeito hidrofóbico. 2004. 257 f. Tese (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ.por
dc.identifier.citationAlmeida, Paulo Afonso de. Mesoiônicos da Classe 1,3-Ditiólio-4-Tiolatos: síntese, reações de cicloadição 1,3-Dipolar e estudo do efeito hidrofóbico. 2004. 257 f. Tese (Programa de Pós-Graduação em Química) - Universidade Federal Rural do Rio de Janeiro, Seropédica-RJ.por
dc.identifier.urihttps://rima.ufrrj.br/jspui/handle/20.500.14407/10230-
dc.description.abstractOs compostos mesoiônicos despertam muito a atenção por serem heterocíclicos dipolares de estruturas não convencionais, apresentando uma atividade biológica muito diversificada e, também, por serem intermediários em reações de cicloadição, para a obtenção de novos derivados heterocíclicos. Neste trabalho foram sintetizados 17 novos derivados mesoiônicos, da classe dos 1,3-ditiólio-4-tiolatos, incluindo uma série homóloga de 13 derivados 2-N-morfolino-5- alquil-1,3-ditiólio-4-tiolatos. Os derivados 2-N-morfolino-5-etil-1,3-ditiólio-4-tiolatos e 2-N-morfolino-5- tetradecil-1,3-ditiólio-4-tiolatos foram submetidos a reações de cicloadição 1,3-dipolar frente a dipolarófilos usuais, como DMAD e ácido fenilpropiólico, gerando 8 novos derivados tiofênicos. Todos os novos derivados mesoiônicos e tiofênicos foram devidamente caracterizados por pontos de fusão, técnicas espectroscópicas de IV, RMN de 1H e 13C (incluindo técnicas heteronucleares bidimensionais) e técnica espectrométrica de massas. A espectrofotometria de UV foi utilizada somente para os derivados mesoiônicos da série homóloga. Todos os derivados mesoiônicos foram submetidos a ensaios de toxicidade geral frente a Artemia salina Leach. Foi feito um estudo do efeito hidrofóbico dos derivados mesoiônicos da série homóloga 5-alquil substituídos, correlacionando-se a toxicidez geral frente a Artemia salina versus o número de carbonos da cadeia alquílica e também versus a hidrofobicidade na forma de logPpor
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico - CNPqpor
dc.formatapplication/pdf*
dc.languageporpor
dc.publisherUniversidade Federal Rural do Rio de Janeiropor
dc.rightsAcesso Abertopor
dc.subjectSíntesepor
dc.subjectCompostos Mesoiônicospor
dc.subjectReações de Cicloadição 1,3-Dipolarpor
dc.subjectEfeito Hidrofóbicopor
dc.subjectToxidez geralpor
dc.subjectArtemia salinapor
dc.subjectSinthesiseng
dc.subjectMesoionic compoundseng
dc.subjecthydrophobic effecteng
dc.subjectArtemia salinaeng
dc.subjectheterocyclic derivativeseng
dc.subject1,3-dipolar cycloaddition reactionseng
dc.titleMesoiônicos da Classe 1,3-Ditiólio-4-Tiolatos: síntese, reações de cicloadição 1,3-Dipolar e estudo do efeito hidrofóbicopor
dc.title.alternativeMesoionic Derivatives from the 1,3-Dithiolium- 4- Thiolate Class: Synthesis, 1,3-Dipolar Cycloaddition Reactions and Hydrophobic Effect Studypor
dc.typeTesepor
dc.description.abstractOtherThe mesoionic compounds have been receiving much attention because of their dipolar special structures and wide-ranging biological activities, they have also being utilized as cycloaddition reactions intermediates to afford new heterocyclic derivatives. In this work 17 new mesoionic derivatives were synthesised from the 1,3- dithiolium-4-thiolate class, including a homologous series of 13 2-N-morpholino-5- alkyl-1,3-dithiolium-4-thiolate. The 2-N-morpholino-5-ethyl- and 2-N-morpholino-5-tetradecyl-1,3- dithiolium-5-thiolates were submitted at 1,3-dipolar cycloaddition reactions against DMAD and phenylpropiolic acid as dipolarophiles affording 8 new thiophenic derivatives. The experimental results were in agreement with the theoretical studies employing semi-empirical molecular modelling methods. All heterocyclic derivatives were fully characterised by spectroscopic techniques, IR, 1H and 13C NMR (1D and 2D experiments) and MS. The UV spectroscopy was utilised only for the homologous mesoionic series. The mesoionic derivatives were assayed against Artemia salina Leach in the general toxicity tests. The hydrophobic effect was studied on mesoionic derivatives of the 5-alkyl homologous series, correlating the Artemia salina general toxicity versus lateral chain number carbon atoms, and the logP values. The results indicated a bell-shaped relationship between the number of carbon of side chain in mesoionic derivatives and LD50 in brine shrimp toxicity assays. The experimental results were in agreement with the theoretical studies which were employing semi-empirical molecular modelling methods. All heterocyclic derivatives were fully characterized by spectroscopic techniques, IR, 1H and 13C NMR (1D and 2D experiments), and MS. The UV spectroscopy was utilized only for the homologous mesoionic serieseng
dc.contributor.advisor1Lima, Aurea Echevarria Aznar Neves
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/1879077396134052por
dc.contributor.referee1Lima, Aurea Echevarria Aznar Neves
dc.contributor.referee2Braz Filho, Raimundo
dc.contributor.referee3Boechat, Núbia
dc.contributor.referee4Lima, Marco Edilson Freire de
dc.contributor.referee5Costa, João Batista Neves da
dc.creator.Latteshttp://lattes.cnpq.br/4266221191908452por
dc.publisher.countryBrasilpor
dc.publisher.departmentInstituto de Ciências Exataspor
dc.publisher.initialsUFRRJpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
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dc.subject.cnpqQuímicapor
dc.thumbnail.urlhttps://tede.ufrrj.br/retrieve/63677/2004%20-%20Paulo%20Afonso%20de%20Almeida.pdf.jpg*
dc.originais.urihttps://tede.ufrrj.br/jspui/handle/jspui/4308
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