Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona
Autor(a) principal: | |
---|---|
Data de Publicação: | 2001 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422001000500006 |
Resumo: | Chalcone (1) and its fluorinated derivatives 2-4, as well as their cyclic analogues 5-10, were synthesized through an aldol condensation reaction between the corresponding ketone and aldehyde. These compounds were characterized by IR, EIMS and ¹H and 13C NMR spectral data. Modern NMR techniques allowed us to conclude that the compounds obtained show E configuration. These techniques were also employed to investigate the equilibrium involving the s-cis and s-trans conformations of 1-4, with this equilibrium being dependent on the fluorine substitution on both aromatic rings, A or B. IR studies indicated that the yield of the s-cis conformation in the fluorinated derivatives is 57.4±1.4; 88.1±0.4 and 66.4±0.7%, for 2, 3 and 4, respectively, based on previous ¹H NMR calculations for chalcone. Theoretical calculations, using the MMX method, were employed to justify the variation of chemical shifts for the fluorinated derivatives and cyclic analogues. These chemical shifts are consequence of the anisotropic effect showed by the carbonyl group on these compounds. |
id |
SBQ-3_e41948504b5137ea612d87309c7d1a54 |
---|---|
oai_identifier_str |
oai:scielo:S0100-40422001000500006 |
network_acronym_str |
SBQ-3 |
network_name_str |
Química Nova (Online) |
repository_id_str |
|
spelling |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalconachalconeconformational equilibriumspectral dataChalcone (1) and its fluorinated derivatives 2-4, as well as their cyclic analogues 5-10, were synthesized through an aldol condensation reaction between the corresponding ketone and aldehyde. These compounds were characterized by IR, EIMS and ¹H and 13C NMR spectral data. Modern NMR techniques allowed us to conclude that the compounds obtained show E configuration. These techniques were also employed to investigate the equilibrium involving the s-cis and s-trans conformations of 1-4, with this equilibrium being dependent on the fluorine substitution on both aromatic rings, A or B. IR studies indicated that the yield of the s-cis conformation in the fluorinated derivatives is 57.4±1.4; 88.1±0.4 and 66.4±0.7%, for 2, 3 and 4, respectively, based on previous ¹H NMR calculations for chalcone. Theoretical calculations, using the MMX method, were employed to justify the variation of chemical shifts for the fluorinated derivatives and cyclic analogues. These chemical shifts are consequence of the anisotropic effect showed by the carbonyl group on these compounds.Sociedade Brasileira de Química2001-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422001000500006Química Nova v.24 n.5 2001reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422001000500006info:eu-repo/semantics/openAccessCesarin-Sobrinho,DariNetto-Ferreira,José CarlosBraz-Filho,Raimundopor2001-11-08T00:00:00Zoai:scielo:S0100-40422001000500006Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2001-11-08T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
title |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
spellingShingle |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona Cesarin-Sobrinho,Dari chalcone conformational equilibrium spectral data |
title_short |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
title_full |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
title_fullStr |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
title_full_unstemmed |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
title_sort |
Efeito da substituição por átomos de flúor no equilíbrio conformacional de chalcona |
author |
Cesarin-Sobrinho,Dari |
author_facet |
Cesarin-Sobrinho,Dari Netto-Ferreira,José Carlos Braz-Filho,Raimundo |
author_role |
author |
author2 |
Netto-Ferreira,José Carlos Braz-Filho,Raimundo |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Cesarin-Sobrinho,Dari Netto-Ferreira,José Carlos Braz-Filho,Raimundo |
dc.subject.por.fl_str_mv |
chalcone conformational equilibrium spectral data |
topic |
chalcone conformational equilibrium spectral data |
description |
Chalcone (1) and its fluorinated derivatives 2-4, as well as their cyclic analogues 5-10, were synthesized through an aldol condensation reaction between the corresponding ketone and aldehyde. These compounds were characterized by IR, EIMS and ¹H and 13C NMR spectral data. Modern NMR techniques allowed us to conclude that the compounds obtained show E configuration. These techniques were also employed to investigate the equilibrium involving the s-cis and s-trans conformations of 1-4, with this equilibrium being dependent on the fluorine substitution on both aromatic rings, A or B. IR studies indicated that the yield of the s-cis conformation in the fluorinated derivatives is 57.4±1.4; 88.1±0.4 and 66.4±0.7%, for 2, 3 and 4, respectively, based on previous ¹H NMR calculations for chalcone. Theoretical calculations, using the MMX method, were employed to justify the variation of chemical shifts for the fluorinated derivatives and cyclic analogues. These chemical shifts are consequence of the anisotropic effect showed by the carbonyl group on these compounds. |
publishDate |
2001 |
dc.date.none.fl_str_mv |
2001-10-01 |
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=S0100-40422001000500006 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422001000500006 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
10.1590/S0100-40422001000500006 |
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 |
Química Nova v.24 n.5 2001 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318102053126144 |