Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds
Autor(a) principal: | |
---|---|
Data de Publicação: | 2016 |
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=S0103-50532016001202322 |
Resumo: | The crystal structures of (Z)-1-phenyl-4-[((2-phenylhydrazono)methyl)]-1H-1,2,3-triazole, (Z)-4-[(2-(2,4-dimethylphenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, (E)-4-[(2-(2,4-dinitrophenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, and (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide dihydrate are reported. The formations of (Z)- configurations about the C=N bonds in the first two compounds arise from the stabilizing presence of intramolecular N-H···N hydrogen bonds, while in the third compound, the presence of intramolecular N-H···O hydrogen bonds promotes an (E) geometry. The arrangement about the CONHC=N fragment in the hydrated acylhydrazone is EC(O)NH/EC=N. Also present in (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide is an interesting R44(8) ring formed from hydrogen bonds generated from four water molecules. Significant π···π stacking interactions are exhibited in three compounds, but not in the least planar first compound, in which the dominant intermolecular interactions are C-H···π interactions. Other intermolecular interactions in one of the compounds are C-H···π interactions, in another compound are C-H···O hydrogen bonds and N-O···π interactions, and in the last compound are O-H···X (X = O and N), N-H···O and C-H···O hydrogen bonds. |
id |
SBQ-2_c77e066e334a4cbd95758bf3cdb095e6 |
---|---|
oai_identifier_str |
oai:scielo:S0103-50532016001202322 |
network_acronym_str |
SBQ-2 |
network_name_str |
Journal of the Brazilian Chemical Society (Online) |
repository_id_str |
|
spelling |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bondsbenzotriazoleshydrazonesacylhydrazoneshydratesintermolecular interactionsThe crystal structures of (Z)-1-phenyl-4-[((2-phenylhydrazono)methyl)]-1H-1,2,3-triazole, (Z)-4-[(2-(2,4-dimethylphenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, (E)-4-[(2-(2,4-dinitrophenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, and (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide dihydrate are reported. The formations of (Z)- configurations about the C=N bonds in the first two compounds arise from the stabilizing presence of intramolecular N-H···N hydrogen bonds, while in the third compound, the presence of intramolecular N-H···O hydrogen bonds promotes an (E) geometry. The arrangement about the CONHC=N fragment in the hydrated acylhydrazone is EC(O)NH/EC=N. Also present in (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide is an interesting R44(8) ring formed from hydrogen bonds generated from four water molecules. Significant π···π stacking interactions are exhibited in three compounds, but not in the least planar first compound, in which the dominant intermolecular interactions are C-H···π interactions. Other intermolecular interactions in one of the compounds are C-H···π interactions, in another compound are C-H···O hydrogen bonds and N-O···π interactions, and in the last compound are O-H···X (X = O and N), N-H···O and C-H···O hydrogen bonds.Sociedade Brasileira de Química2016-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202322Journal of the Brazilian Chemical Society v.27 n.12 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160129info:eu-repo/semantics/openAccessGonzaga,Daniel T. G.Silva,Fernando C. daFerreira,Vitor F.Wardell,James L.Wardell,Solange M. S. V.eng2016-12-01T00:00:00Zoai:scielo:S0103-50532016001202322Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
title |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
spellingShingle |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds Gonzaga,Daniel T. G. benzotriazoles hydrazones acylhydrazones hydrates intermolecular interactions |
title_short |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
title_full |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
title_fullStr |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
title_full_unstemmed |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
title_sort |
Crystal Structures of 1-Aryl-1H- and 2-Aryl-2H-1,2,3-triazolyl Hydrazones. Conformational Consequences of Different Classical Hydrogen Bonds |
author |
Gonzaga,Daniel T. G. |
author_facet |
Gonzaga,Daniel T. G. Silva,Fernando C. da Ferreira,Vitor F. Wardell,James L. Wardell,Solange M. S. V. |
author_role |
author |
author2 |
Silva,Fernando C. da Ferreira,Vitor F. Wardell,James L. Wardell,Solange M. S. V. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Gonzaga,Daniel T. G. Silva,Fernando C. da Ferreira,Vitor F. Wardell,James L. Wardell,Solange M. S. V. |
dc.subject.por.fl_str_mv |
benzotriazoles hydrazones acylhydrazones hydrates intermolecular interactions |
topic |
benzotriazoles hydrazones acylhydrazones hydrates intermolecular interactions |
description |
The crystal structures of (Z)-1-phenyl-4-[((2-phenylhydrazono)methyl)]-1H-1,2,3-triazole, (Z)-4-[(2-(2,4-dimethylphenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, (E)-4-[(2-(2,4-dinitrophenyl)hydrazono)methyl]-2-phenyl-2H-1,2,3-triazole, and (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide dihydrate are reported. The formations of (Z)- configurations about the C=N bonds in the first two compounds arise from the stabilizing presence of intramolecular N-H···N hydrogen bonds, while in the third compound, the presence of intramolecular N-H···O hydrogen bonds promotes an (E) geometry. The arrangement about the CONHC=N fragment in the hydrated acylhydrazone is EC(O)NH/EC=N. Also present in (E)-N'-((2-phenyl-2H-1,2,3-triazol-4-yl)methylene)isonicotinohydrazide is an interesting R44(8) ring formed from hydrogen bonds generated from four water molecules. Significant π···π stacking interactions are exhibited in three compounds, but not in the least planar first compound, in which the dominant intermolecular interactions are C-H···π interactions. Other intermolecular interactions in one of the compounds are C-H···π interactions, in another compound are C-H···O hydrogen bonds and N-O···π interactions, and in the last compound are O-H···X (X = O and N), N-H···O and C-H···O hydrogen bonds. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-12-01 |
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=S0103-50532016001202322 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202322 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20160129 |
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.27 n.12 2016 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 |
_version_ |
1750318179102490624 |