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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Volume 73, Issue 8


π-Electron delocalization in 2-benzoyl-5-phenylpyrazolidin-3-one

Monika Olesiejuk
  • Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Agnieszka Kudelko
  • Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Katarzyna Gajda / Błażej Dziuk / Krzysztof Ejsmont
Published Online: 2018-07-09 | DOI: https://doi.org/10.1515/znb-2018-0072


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.

Keywords: addition; benzhydrazide; crystal structure; X-ray structure determination


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About the article

Received: 2018-04-16

Accepted: 2018-06-05

Published Online: 2018-07-09

Published in Print: 2018-08-28

Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 8, Pages 577–582, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0072.

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