π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one
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Monika Olesiejuk
und
Krzysztof Ejsmont
Abstract
The crystal and molecular structures of 2-benzoyl-5-phenylpyrazolidin-3-one have been characterized by X-ray diffraction along with density functional theory studies. Cinnamic acid chloride was reacted with benzhydrazide, yielding 2-benzoyl-5-phenylpyrazolidin-3-one. This product was formed in the transformation comprising the nucleophilic addition of benzhydrazide to the styryl fragment of the α,β-unsaturated arrangement and subsequent cyclization. The molecule contains two benzene rings and one five-membered heterocyclic ring with an N–N single bond. The five-membered ring is composed of three atoms of sp3 hybridization and two atoms of sp2 hybridization, which cause the flattening of the heterocyclic ring. The Harmonic Oscillator Model of Aromaticity and Nucleus-Independent Chemical Shift indexes, calculated for the benzene rings, demonstrate that there are no substantial interactions between the regions of π-electron delocalization in the molecule. In the crystal structure, there are N–H···O hydrogen bonds that link the molecules along the crystallographic c axis and weak intermolecular C–H···O hydrogen bonds.
Acknowledgements
The authors are thankful for the calculation facilities and software. Calculations were carried out at the Wroclaw Centre for Networking and Supercomputing (http://www.wcss.pl), grant no. 311.
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©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- In this Issue
- The lanthanide hydride oxides SmHO and HoHO
- Longiflorol, a bergenin α-d-apioside from the stem bark of Diospyros longiflora, and its antioxidant activity
- An expedient synthesis of 6-amino-5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(aryl)methyl]-1,3-dimethyl-2,4,6(1H,3H)-pyrimidinedione derivatives using Fe3O4@TiO2 nanocomposite as an efficient, magnetically separable, and reusable catalyst
- Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
- Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines
- The 3D supramolecular architecture of copper(II) 6-methyl-2-pyridone-4-carboxylate: synthesis, structure, magnetic behavior and DFT studies
- Synthesis, crystal structure, and magnetic properties of the complex [(CH3)3NH]2 [Co(NCS)4]
- π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one
- Oxidative coupling of cycloalkanones with 3-(pyridin-2-yl)-1,2,4-triazinone coordinated to Pd(II)
- Influence of high-energy ball milling and additives on the formation of sphere-like α-Al2O3 powder by high-temperature calcination
- Encapsulation of ferrocenes by hydrogen-bonded pyrogallol[4]arene dimers
- Syntheses and crystal structures of guanidine hydrochlorides with two Schiff base functions as efficient colorimetric and selective sensors for fluoride
Artikel in diesem Heft
- Frontmatter
- In this Issue
- The lanthanide hydride oxides SmHO and HoHO
- Longiflorol, a bergenin α-d-apioside from the stem bark of Diospyros longiflora, and its antioxidant activity
- An expedient synthesis of 6-amino-5-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(aryl)methyl]-1,3-dimethyl-2,4,6(1H,3H)-pyrimidinedione derivatives using Fe3O4@TiO2 nanocomposite as an efficient, magnetically separable, and reusable catalyst
- Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
- Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines
- The 3D supramolecular architecture of copper(II) 6-methyl-2-pyridone-4-carboxylate: synthesis, structure, magnetic behavior and DFT studies
- Synthesis, crystal structure, and magnetic properties of the complex [(CH3)3NH]2 [Co(NCS)4]
- π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one
- Oxidative coupling of cycloalkanones with 3-(pyridin-2-yl)-1,2,4-triazinone coordinated to Pd(II)
- Influence of high-energy ball milling and additives on the formation of sphere-like α-Al2O3 powder by high-temperature calcination
- Encapsulation of ferrocenes by hydrogen-bonded pyrogallol[4]arene dimers
- Syntheses and crystal structures of guanidine hydrochlorides with two Schiff base functions as efficient colorimetric and selective sensors for fluoride
