Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations

The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phen...

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Detalles Bibliográficos
Autores principales: Saeed, Aamer, Khurshid, Asma, Flörke, Ulrich, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Gil, Diego M, Rocha, Mariana, Frontera, Antonio, El-Seedi, Hesham R., Mumtaz, Amara, Erben, Mauricio Federico
Formato: Articulo
Lenguaje:Inglés
Publicado: 2020
Materias:
Química
Antipyrine derivatives
X-ray structure
Non-covalent interactions
Hirshfeld surfaces
Energy frameworks
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/146542
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-146542
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Antipyrine derivatives
X-ray structure
Non-covalent interactions
Hirshfeld surfaces
Energy frameworks
spellingShingle Química
Antipyrine derivatives
X-ray structure
Non-covalent interactions
Hirshfeld surfaces
Energy frameworks
Saeed, Aamer
Khurshid, Asma
Flörke, Ulrich
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Gil, Diego M
Rocha, Mariana
Frontera, Antonio
El-Seedi, Hesham R.
Mumtaz, Amara
Erben, Mauricio Federico
Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
topic_facet Química
Antipyrine derivatives
X-ray structure
Non-covalent interactions
Hirshfeld surfaces
Energy frameworks
description The synthesis, X-ray structure characterization, Hirshfeld surface analysis and DFT calculations of two new antipyrine derivatives are reported herein. Particularly, 2-bromo-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (2) are synthesized in good yields and characterized spectroscopically. Both compounds are isostructural and crystallize in the monoclinic P21/c space group. The crystal packing of both compounds is mainly stabilized by a combination of N–H⋯O and C–H⋯O hydrogen bonds. In addition, C–H⋯π and lone pair⋯π contacts were observed. Their solid-state structures have been analyzed through Hirshfeld surface analysis, including the evaluation of the different energy frameworks, indicating that the molecular sheets are primarily formed by hydrogen bonds and the stabilization is dominated via the electrostatic energy contribution. These studies are complemented with DFT calculations (B3LYP-D3/def2-TZVP), and a combination of QTAIM/NCIplot analyses disclosing that the H-bonding interactions are energetically relevant (ranging from 0.9 to 6.1 kcal mol−1), however the total binding energies of the different assemblies are dominated by a combination of π-interactions (of the type C–H⋯π, π⋯π, and lone pair halogen⋯π) that are able to stabilize cooperatively the assemblies up to 12 kcal mol−1.
format Articulo
Articulo
author Saeed, Aamer
Khurshid, Asma
Flörke, Ulrich
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Gil, Diego M
Rocha, Mariana
Frontera, Antonio
El-Seedi, Hesham R.
Mumtaz, Amara
Erben, Mauricio Federico
author_facet Saeed, Aamer
Khurshid, Asma
Flörke, Ulrich
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Gil, Diego M
Rocha, Mariana
Frontera, Antonio
El-Seedi, Hesham R.
Mumtaz, Amara
Erben, Mauricio Federico
author_sort Saeed, Aamer
title Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_short Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_full Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_fullStr Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_full_unstemmed Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
title_sort intermolecular interactions in antipyrine-like derivatives 2-halo-n-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)benzamides: x-ray structure, hirshfeld surface analysis and dft calculations
publishDate 2020
url http://sedici.unlp.edu.ar/handle/10915/146542
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