Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities
Autor(a) principal: | |
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Data de Publicação: | 2010 |
Outros Autores: | , , , , |
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=S0103-50532010000400022 |
Resumo: | Stereoelectronic properties of nitro-heterocyclic bioisosteric congeners were investigated using theory-level quantum chemistry and cyclic voltammetry with the goal of determining physico-chemical properties that affect the redox potential of the nitro group. Molecular geometry, physicochemical properties and stereoelectronic surfaces, such as molecular electrostatic potential, and HOMO and LUMO orbitalar distributions, were calculated using the AM1 semiempirical method. The redox potential of nitro-heterocyclic compounds, which corresponds to the (Ar-NO2/Ar-NO2- ) redox couple, was measured in aprotic media (DMSO and 0.1 mol L-1 Bu4NH4BF4) using glassy carbon as working electrode, Pt wire, Ag/AgCl, KCl(sat) as counter and reference electrodes, respectively. Analysis of minimal energy conformers of all derivatives indicated a break in structural planarity located between the hydrazine nitrogen and benzamide moiety. No statistical correlation was obtained using the PLS regression method, taking in account all physicochemical properties and the redox potential, which might result from the lack of coplanarity effect in the molecular structure of the compounds. |
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Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities5-nitro-heterocyclicstereoelectronic propertiesredox potentialStereoelectronic properties of nitro-heterocyclic bioisosteric congeners were investigated using theory-level quantum chemistry and cyclic voltammetry with the goal of determining physico-chemical properties that affect the redox potential of the nitro group. Molecular geometry, physicochemical properties and stereoelectronic surfaces, such as molecular electrostatic potential, and HOMO and LUMO orbitalar distributions, were calculated using the AM1 semiempirical method. The redox potential of nitro-heterocyclic compounds, which corresponds to the (Ar-NO2/Ar-NO2- ) redox couple, was measured in aprotic media (DMSO and 0.1 mol L-1 Bu4NH4BF4) using glassy carbon as working electrode, Pt wire, Ag/AgCl, KCl(sat) as counter and reference electrodes, respectively. Analysis of minimal energy conformers of all derivatives indicated a break in structural planarity located between the hydrazine nitrogen and benzamide moiety. No statistical correlation was obtained using the PLS regression method, taking in account all physicochemical properties and the redox potential, which might result from the lack of coplanarity effect in the molecular structure of the compounds.Sociedade Brasileira de Química2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000400022Journal of the Brazilian Chemical Society v.21 n.4 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532010000400022info:eu-repo/semantics/openAccessPaula,Fávero R.Trossini,Gustavo H. G.Ferreira,Elizabeth I.Serrano,Silvia H. P.Menezes,Carla M. S.Tavares,Leoberto C.eng2010-05-21T00:00:00Zoai:scielo:S0103-50532010000400022Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-05-21T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
title |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
spellingShingle |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities Paula,Fávero R. 5-nitro-heterocyclic stereoelectronic properties redox potential |
title_short |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
title_full |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
title_fullStr |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
title_full_unstemmed |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
title_sort |
Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities |
author |
Paula,Fávero R. |
author_facet |
Paula,Fávero R. Trossini,Gustavo H. G. Ferreira,Elizabeth I. Serrano,Silvia H. P. Menezes,Carla M. S. Tavares,Leoberto C. |
author_role |
author |
author2 |
Trossini,Gustavo H. G. Ferreira,Elizabeth I. Serrano,Silvia H. P. Menezes,Carla M. S. Tavares,Leoberto C. |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Paula,Fávero R. Trossini,Gustavo H. G. Ferreira,Elizabeth I. Serrano,Silvia H. P. Menezes,Carla M. S. Tavares,Leoberto C. |
dc.subject.por.fl_str_mv |
5-nitro-heterocyclic stereoelectronic properties redox potential |
topic |
5-nitro-heterocyclic stereoelectronic properties redox potential |
description |
Stereoelectronic properties of nitro-heterocyclic bioisosteric congeners were investigated using theory-level quantum chemistry and cyclic voltammetry with the goal of determining physico-chemical properties that affect the redox potential of the nitro group. Molecular geometry, physicochemical properties and stereoelectronic surfaces, such as molecular electrostatic potential, and HOMO and LUMO orbitalar distributions, were calculated using the AM1 semiempirical method. The redox potential of nitro-heterocyclic compounds, which corresponds to the (Ar-NO2/Ar-NO2- ) redox couple, was measured in aprotic media (DMSO and 0.1 mol L-1 Bu4NH4BF4) using glassy carbon as working electrode, Pt wire, Ag/AgCl, KCl(sat) as counter and reference electrodes, respectively. Analysis of minimal energy conformers of all derivatives indicated a break in structural planarity located between the hydrazine nitrogen and benzamide moiety. No statistical correlation was obtained using the PLS regression method, taking in account all physicochemical properties and the redox potential, which might result from the lack of coplanarity effect in the molecular structure of the compounds. |
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=S0103-50532010000400022 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000400022 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532010000400022 |
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.4 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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1750318170715979776 |