dc.creator | Mallmann, Anderson Stoffels | |
dc.date.accessioned | 2017-05-10 | |
dc.date.available | 2017-05-10 | |
dc.date.issued | 2008-12-05 | |
dc.identifier.citation | MALLMANN, Anderson Stoffels. "Synthesis of pentafluoropropionylated cyclodextrins and its development as chiral stationary phases in enantioselective gas chromatography . 2008. 142 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. | por |
dc.identifier.uri | http://repositorio.ufsm.br/handle/1/4177 | |
dc.description.abstract | Three new α, β- and γ-cyclodextrins derivatives were synthesized: hexakis-(2,6-di-O-pentyl)-α-cyclodextrin, heptakis-(2,6-di-O-pentyl)-β-cyclodextrin and octakis-(2,6-di-O-pentyl)-γ-cyclodextrin. The structures were elucidated using Nuclear Magnetic Resonance techniques such 1H, 13C, COSY 1H-1H and HMQC. Three new chiral chromatographic columns were prepared with the
obtained chiral phases and the achiral phase OV 1701. All the columns were tested with various racemic compounds, showing efficiency in their chiral resolution such as: alcohols, acetylated alcohols, trifluoroacetylated alcohols, aminoacids, organic acids esters, monoterpenic hydrocarbons, ketones, lactones, drugs, sulphur compounds, selenium compounds and halogenated compounds. The column confeccionated with the stationary phase 2,6-Pe-3-PFP-α-CD/OV 1701 (1:1) showed better results on the separation of (+/-)-menthol-OAc and (+/-)-borneol. Many compounds were tested and separated by the chiral column 2,6-Pe-3-PFP-β-CD/ OV 1701 (1:1). Good results were obtained on the stereoselective separation of (+/-)-2-decanol-O-Ac, (+/-)-2-decanol-O-TFA, (+/-)-2-undecanol-O-Ac,(+/-)-2-undecanol-O-TFA, (+/-)-phenylethanol-O-Ac, (+/-)-phenylpropanol-O-Ac, (+/-)- borneol-O-Ac, (+/-)-borneol-O-TFA, (+/-)-menthol-O-Ac, (+/-)-2-phenyl-2-butanol-OAc, (+/-)-2-phenyl-2-pentanol-O-Ac, D,L-alanine-O-ethyl, R,S-(E)-ethyl-2-(4-oxopent- 2-en-2-ilamino)propanoate, (+/-)-2,3- bromopropionic acid, (+/-)-mandelic acid, (+/-)-α -
pinene, (+/-)-camphor, (+/-)-carvone, (+/-)-α-ionone, (+/-)-amphetamine, (+/-)-cyclohexyl benzenesulfinate, (+/-)-1-(ethylsulfinyl)benzene, (+/-)-1- (methylsulfinyl)benzene, (+/-)-1-(methylsulfinyl)-4-methyl benzene and (+/-)-1-
(ethylsulfinyl)-4-methyl benzene. The columns with 2,6-Pe-3-PFP-γ-CD/ OV 1701 (1:1) showed good results on the separations of (+/-)-borneol, (+/-)-borneol-O-Ac, (+/-)-borneol-O-TFA, (+/-)-neo-menthol, (+/-)-menthol-O-Ac, (+/-)-2-decanol-O-Ac, (+/-)-2-undecanol-O-Ac, D,L-leucine, (+/-)-β-hydroxy-leucine, (+/-)-α-pinene, (+/-)-camphor, (+/-)-carvone and (+/-)-α-ionone. | eng |
dc.description.sponsorship | Conselho Nacional de Desenvolvimento Científico e Tecnológico | |
dc.format | application/pdf | por |
dc.language | por | por |
dc.publisher | Universidade Federal de Santa Maria | por |
dc.rights | Acesso Aberto | por |
dc.subject | Fase estacionária | por |
dc.subject | Síntese | por |
dc.subject | Cromatografia | por |
dc.title | Síntese de ciclodextrinas pentafluorpropioniladas e suas aplicações como fases estacionárias quirais em cromatografia gasosa enantiosseletiva | por |
dc.title.alternative | "Synthesis of pentafluoropropionylated cyclodextrins and its development as chiral stationary phases in enantioselective gas chromatography | eng |
dc.type | Tese | por |
dc.description.resumo | Três novos derivados de α-, β - e γ-ciclodextrinas foram sintetizados: Hexaquis-(2,6-di-O-pentil)-α-ciclodextrina, Heptaquis-(2,6-di-O-pentil)-β-ciclodextrina e Octaquis-(2,6-di-O-pentil)-γ-ciclodextrina. Suas estruturas foram elucidadas utilizando-se técnicas de Ressonância Magnética Nuclear de 1H, 13C, COSY 1H-1H e HMQC. Foram confeccionadas três novas colunas cromatográficas quirais com as fases obtidas e com a fase aquiral OV 1701. Todas as colunas foram testadas
frente a vários analitos racêmicos, mostrando-se eficientes na sua resolução estereosseletiva: álcoois, álcoois acetilados e trifluoracetilados, aminoácidos, ésteres de ácidos orgânicos, hidrocarbonetos monoterpênicos, cetonas, lactonas, fármacos
como a anfetamina, compostos com enxofre, compostos com selênio e compostos halogenados. A coluna confeccionada com a fase estacionária 2,6-Pe-3-PFP-α-CD/OV 1701 (1:1) apresentou os melhores resultados na separação enantiomérica do (+/-)-mentol-OAc e do (+/-)-borneol.
Muitos compostos foram testados e separados na coluna quiral 2,6-Pe-3-PFP-β-CD/ OV 1701 (1:1). Os melhores resultados obtidos foram na separação estereosseletiva de: (+/-)-2-decanol-O-Ac, (+/-)-2-decanol-O-TFA, (+/-)-2-undecanol-O-Ac, (+/-)-2-undecanol-O-TFA, (+/-)-feniletanol-O-Ac, (+/-)-fenilpropanol-O-Ac, (+/-)-borneol-O-Ac, (+/-)-borneol-O-TFA, (+/-)-mentol-O-Ac, (+/-)-2-fenil-2-butanol-O-Ac, (+/-)-2-fenil-2-pentanol-O-Ac, D,L-alanina-O-etil, R,S-(E)-etil-2-(4-oxopent-2-en-2-ilamino)propanoate, (+/-)-ácido 2,3-bromopropiônico, (+/-)-ácido mandélico, (+/-)- α -pineno, (+/-)-cânfora, (+/-)-carvona, (+/-)-α-ionona, (+/-)-anfetamina, (+/-)-benzenosulfinato de ciclohexila, (+/-)-1-(etilsulfinil)benzeno, (+/-)-1-(metilsulfinil)benzeno, (+/-)-1-(metilsulfinil)-4-metil benzeno e (+/-)-1-(etilsulfinil)-4-
metil benzeno. A coluna 2,6-Pe-3-PFP-γ-CD/ OV 1701 (1:1) apresentou bons resultados nas separações de: (+/-)-borneol, (+/-)-borneol-O-Ac, (+/-)-borneol-OTFA, (+/-)-neo-mentol, (+/-)-mentol-O-Ac, (+/-)-2-decanol-O-Ac, (+/-)-2-undecanol-OAc, D,L-leucina, (+/-)-β-hidroxi-leucina, (+/-)-α-pineno, (+/-)-cânfora, (+/-)-carvona e (+/-)-α-ionona. | por |
dc.contributor.advisor1 | Morel, Ademir Farias | |
dc.contributor.advisor1Lattes | http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783930A8 | por |
dc.contributor.referee1 | Ethur, Eduardo Miranda | |
dc.contributor.referee1Lattes | http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4791365P7 | por |
dc.contributor.referee2 | Braibante, Mara Elisa Fortes | |
dc.contributor.referee2Lattes | http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788627U5 | por |
dc.contributor.referee3 | Silva, Ubiratan Flores da | |
dc.contributor.referee3Lattes | http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4798054Z3 | por |
dc.creator.Lattes | http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4705296D4 | por |
dc.publisher.country | BR | por |
dc.publisher.department | Química | por |
dc.publisher.initials | UFSM | por |
dc.publisher.program | Programa de Pós-Graduação em Química | por |
dc.subject.cnpq | CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA | por |