NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal
A series of eleven Schiff Bases have been synthesized. They were obtained by condensation of piperonal (3,4-methylenedioxybenzaldehyde) with the corresponding aromatic primary amines. Their ¹H and 13C-NMR spectra have been obtained and the Hammett correlations including chemical shifts and the subsi...
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Sociedade Brasileira de Química
1999-01-01
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doaj-b4e832bb48ca4fb780ecdc99078b713a2020-11-24T21:06:17ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50531999-01-011016064NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from PiperonalEchevarria AureaNascimento Maria da GraçaGerônimo VanildeMiller JosephGiesbrecht AstréaA series of eleven Schiff Bases have been synthesized. They were obtained by condensation of piperonal (3,4-methylenedioxybenzaldehyde) with the corresponding aromatic primary amines. Their ¹H and 13C-NMR spectra have been obtained and the Hammett correlations including chemical shifts and the subsitutent constants (sigmap, sigmaR e sigmaI) were studied. Linear and bilinear significant correlations were observed for iminic carbon (C-alpha) and C-1?, showing a more significant ressonance effect on chemical shifts. The chemical shifts for C-4? were highly affected by substituent effects, especially for halogens in the expected direction. Their biological activity against microorganisms has also been measured and significant activity was showed against Epidermophyton floccosum. The biological activity did not give a reasonable relationship with electronic effects.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000100010Hammett NMR correlationspiperonal |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Echevarria Aurea Nascimento Maria da Graça Gerônimo Vanilde Miller Joseph Giesbrecht Astréa |
spellingShingle |
Echevarria Aurea Nascimento Maria da Graça Gerônimo Vanilde Miller Joseph Giesbrecht Astréa NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal Journal of the Brazilian Chemical Society Hammett NMR correlations piperonal |
author_facet |
Echevarria Aurea Nascimento Maria da Graça Gerônimo Vanilde Miller Joseph Giesbrecht Astréa |
author_sort |
Echevarria Aurea |
title |
NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal |
title_short |
NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal |
title_full |
NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal |
title_fullStr |
NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal |
title_full_unstemmed |
NMR Spectroscopy, Hammett Correlations and Biological Activity of Some Schiff Bases Derived from Piperonal |
title_sort |
nmr spectroscopy, hammett correlations and biological activity of some schiff bases derived from piperonal |
publisher |
Sociedade Brasileira de Química |
series |
Journal of the Brazilian Chemical Society |
issn |
0103-5053 |
publishDate |
1999-01-01 |
description |
A series of eleven Schiff Bases have been synthesized. They were obtained by condensation of piperonal (3,4-methylenedioxybenzaldehyde) with the corresponding aromatic primary amines. Their ¹H and 13C-NMR spectra have been obtained and the Hammett correlations including chemical shifts and the subsitutent constants (sigmap, sigmaR e sigmaI) were studied. Linear and bilinear significant correlations were observed for iminic carbon (C-alpha) and C-1?, showing a more significant ressonance effect on chemical shifts. The chemical shifts for C-4? were highly affected by substituent effects, especially for halogens in the expected direction. Their biological activity against microorganisms has also been measured and significant activity was showed against Epidermophyton floccosum. The biological activity did not give a reasonable relationship with electronic effects. |
topic |
Hammett NMR correlations piperonal |
url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000100010 |
work_keys_str_mv |
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