Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

Detalhes bibliográficos
Autor(a) principal: Ferreira,Jeiely G
Data de Publicação: 2010
Outros Autores: Gonçalves,Simone M. C
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002
Resumo: In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.
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spelling Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMRenantiomeric excessderivatizing agentselenium NMRchiral non racemic substratesIn this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.Sociedade Brasileira de Química2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002Journal of the Brazilian Chemical Society v.21 n.11 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532010001100002info:eu-repo/semantics/openAccessFerreira,Jeiely GGonçalves,Simone M. Ceng2010-12-15T00:00:00Zoai:scielo:S0103-50532010001100002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-12-15T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
spellingShingle Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
Ferreira,Jeiely G
enantiomeric excess
derivatizing agent
selenium NMR
chiral non racemic substrates
title_short Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_full Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_fullStr Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_full_unstemmed Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_sort Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
author Ferreira,Jeiely G
author_facet Ferreira,Jeiely G
Gonçalves,Simone M. C
author_role author
author2 Gonçalves,Simone M. C
author2_role author
dc.contributor.author.fl_str_mv Ferreira,Jeiely G
Gonçalves,Simone M. C
dc.subject.por.fl_str_mv enantiomeric excess
derivatizing agent
selenium NMR
chiral non racemic substrates
topic enantiomeric excess
derivatizing agent
selenium NMR
chiral non racemic substrates
description In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.
publishDate 2010
dc.date.none.fl_str_mv 2010-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532010001100002
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.21 n.11 2010
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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