Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone
The compound 1,4-pentadien-3-one,(1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone presents the molecular formula C23H18N4O4 and was prepared in an undergraduate laboratory. The hydrazone was synthesized from the condensation between dibenzalacetone and 2,4-dinitrophenylhydrazine (DNPH) and crystallized employing water/acetone liquid-liquid diffusion. The structure presents three aromatic rings connected by an unsaturated Y-shaped system. Dinitro substituted and one of the other aromatic rings are 15º out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89º). The only observed classical hydrogen bonding is an intramolecular N-H···O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H···O hydrogen bond and C-H···π, polar-π, and π-stacking. An interaction involving NO2···NO2 was also observed.
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Sociedade Brasileira de Química
2021
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oai:scielo:S0103-505320210002004292021-01-28Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazoneLigiéro,Carolina B. P.Monte,Pamella M.Silva,Tiago L. daBarros,José C. crystal structure 2,4-dinitrophenylhydrazine hydrazone The compound 1,4-pentadien-3-one,(1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone presents the molecular formula C23H18N4O4 and was prepared in an undergraduate laboratory. The hydrazone was synthesized from the condensation between dibenzalacetone and 2,4-dinitrophenylhydrazine (DNPH) and crystallized employing water/acetone liquid-liquid diffusion. The structure presents three aromatic rings connected by an unsaturated Y-shaped system. Dinitro substituted and one of the other aromatic rings are 15º out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89º). The only observed classical hydrogen bonding is an intramolecular N-H···O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H···O hydrogen bond and C-H···π, polar-π, and π-stacking. An interaction involving NO2···NO2 was also observed.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.32 n.2 20212021-02-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000200429en10.21577/0103-5053.20200195 |
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Ligiéro,Carolina B. P. Monte,Pamella M. Silva,Tiago L. da Barros,José C. |
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Ligiéro,Carolina B. P. Monte,Pamella M. Silva,Tiago L. da Barros,José C. Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| author_facet |
Ligiéro,Carolina B. P. Monte,Pamella M. Silva,Tiago L. da Barros,José C. |
| author_sort |
Ligiéro,Carolina B. P. |
| title |
Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| title_short |
Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| title_full |
Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| title_fullStr |
Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| title_full_unstemmed |
Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| title_sort |
crystal structure and hirshfeld surface analysis of 1,4-pentadien-3-one, (1e,4e)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone |
| description |
The compound 1,4-pentadien-3-one,(1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone presents the molecular formula C23H18N4O4 and was prepared in an undergraduate laboratory. The hydrazone was synthesized from the condensation between dibenzalacetone and 2,4-dinitrophenylhydrazine (DNPH) and crystallized employing water/acetone liquid-liquid diffusion. The structure presents three aromatic rings connected by an unsaturated Y-shaped system. Dinitro substituted and one of the other aromatic rings are 15º out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89º). The only observed classical hydrogen bonding is an intramolecular N-H···O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H···O hydrogen bond and C-H···π, polar-π, and π-stacking. An interaction involving NO2···NO2 was also observed. |
| publisher |
Sociedade Brasileira de Química |
| publishDate |
2021 |
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http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000200429 |
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