Please use this identifier to cite or link to this item:
Title: Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach
Authors: Milovanović, Vesna
Petrović, Zorica
Novakovic, Sladjana B.
Bogdanovic, Goran A.
Simijonović, Dušica
Petrović, Vladimir
Issue Date: 2019
Abstract: © 2019 Elsevier B.V. Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported.
Type: article
DOI: 10.1016/j.molstruc.2019.05.095
ISSN: 0022-2860
SCOPUS: 2-s2.0-85066467734
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac

Page views(s)




Files in This Item:
File Description SizeFormat 
  Restricted Access
29.86 kBAdobe PDFThumbnail

Items in SCIDAR are protected by copyright, with all rights reserved, unless otherwise indicated.