Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition

Detalhes bibliográficos
Autor(a) principal: Sintra, Tânia E.
Data de Publicação: 2019
Outros Autores: Gantman, Mikhail G., Ventura, Sónia P. M., Coutinho, João A. P., Wasserscheid, Peter, Schulz, Peter S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10773/30229
Resumo: The separation of enantiomers remains a major challenge for the pharmaceutical industry. In this work, eight chiral ionic liquids (CILs) directly derived from the ‘chiral pool’ were synthesized and characterized in order to develop enantioselective systems, for the chiral resolution. According to their chiral cations, three different groups of CILs were prepared, namely based on quinine, L-proline and L-valine, and their enantiomeric recognition ability evaluated. For that purpose the diastereomeric interactions between a racemic mixture of Mosher's acid sodium salt and each CIL were studied using 19 F NMR spectroscopy. The remarkable chemical shift dispersion induced by some CILs demonstrates their potential application in chiral resolution. Additionally the optical rotation, thermophysical properties and ecotoxicity against the marine bacteria Aliivibrio fischeri of these chiral ionic liquids were addressed.
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spelling Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognitionChiral ionic liquidsChiral resolutionEcotoxicityEnantioselectivityMosher's acidThermophysical propertiesThe separation of enantiomers remains a major challenge for the pharmaceutical industry. In this work, eight chiral ionic liquids (CILs) directly derived from the ‘chiral pool’ were synthesized and characterized in order to develop enantioselective systems, for the chiral resolution. According to their chiral cations, three different groups of CILs were prepared, namely based on quinine, L-proline and L-valine, and their enantiomeric recognition ability evaluated. For that purpose the diastereomeric interactions between a racemic mixture of Mosher's acid sodium salt and each CIL were studied using 19 F NMR spectroscopy. The remarkable chemical shift dispersion induced by some CILs demonstrates their potential application in chiral resolution. Additionally the optical rotation, thermophysical properties and ecotoxicity against the marine bacteria Aliivibrio fischeri of these chiral ionic liquids were addressed.Elsevier2021-01-05T16:32:03Z2021-06-01T00:00:00Z2019-06-01T00:00:00Z2019-06-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/30229eng0167-732210.1016/j.molliq.2019.03.084Sintra, Tânia E.Gantman, Mikhail G.Ventura, Sónia P. M.Coutinho, João A. P.Wasserscheid, PeterSchulz, Peter S.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-06T04:29:29Zoai:ria.ua.pt:10773/30229Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-06T04:29:29Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
title Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
spellingShingle Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
Sintra, Tânia E.
Chiral ionic liquids
Chiral resolution
Ecotoxicity
Enantioselectivity
Mosher's acid
Thermophysical properties
title_short Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
title_full Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
title_fullStr Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
title_full_unstemmed Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
title_sort Synthesis and characterization of chiral ionic liquids based on quinine, l-proline and l-valine for enantiomeric recognition
author Sintra, Tânia E.
author_facet Sintra, Tânia E.
Gantman, Mikhail G.
Ventura, Sónia P. M.
Coutinho, João A. P.
Wasserscheid, Peter
Schulz, Peter S.
author_role author
author2 Gantman, Mikhail G.
Ventura, Sónia P. M.
Coutinho, João A. P.
Wasserscheid, Peter
Schulz, Peter S.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Sintra, Tânia E.
Gantman, Mikhail G.
Ventura, Sónia P. M.
Coutinho, João A. P.
Wasserscheid, Peter
Schulz, Peter S.
dc.subject.por.fl_str_mv Chiral ionic liquids
Chiral resolution
Ecotoxicity
Enantioselectivity
Mosher's acid
Thermophysical properties
topic Chiral ionic liquids
Chiral resolution
Ecotoxicity
Enantioselectivity
Mosher's acid
Thermophysical properties
description The separation of enantiomers remains a major challenge for the pharmaceutical industry. In this work, eight chiral ionic liquids (CILs) directly derived from the ‘chiral pool’ were synthesized and characterized in order to develop enantioselective systems, for the chiral resolution. According to their chiral cations, three different groups of CILs were prepared, namely based on quinine, L-proline and L-valine, and their enantiomeric recognition ability evaluated. For that purpose the diastereomeric interactions between a racemic mixture of Mosher's acid sodium salt and each CIL were studied using 19 F NMR spectroscopy. The remarkable chemical shift dispersion induced by some CILs demonstrates their potential application in chiral resolution. Additionally the optical rotation, thermophysical properties and ecotoxicity against the marine bacteria Aliivibrio fischeri of these chiral ionic liquids were addressed.
publishDate 2019
dc.date.none.fl_str_mv 2019-06-01T00:00:00Z
2019-06-01
2021-01-05T16:32:03Z
2021-06-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10773/30229
url http://hdl.handle.net/10773/30229
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0167-7322
10.1016/j.molliq.2019.03.084
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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