Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications

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Shabir G., Hussain G., Saeed A., Hussain T., HÖKELEK T., Erben M. F., ...More

JOURNAL OF MOLECULAR MODELING, vol.27, no.10, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 10
  • Publication Date: 2021
  • Doi Number: 10.1007/s00894-021-04910-1
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, CAB Abstracts, EMBASE, MEDLINE, Veterinary Science Database
  • Keywords: p-Sulphophenyl-3-methyl-5-pyrazolone, Diazotization, Hirshfeld surface analysis, UV, Energy gap, Crystal structure, INTERMOLECULAR INTERACTIONS, QUANTITATIVE-ANALYSIS, CHEMISTRY, ARYLATION, RADICALS
  • Hacettepe University Affiliated: Yes


The title compound is a new pyrazolone derivative which was synthesized starting from p-sulphophenyl-3-methyl-5-pyrazolone (1) by nitrosation at low temperature to afford the corresponding p-sulphophenyl-3-methyl-4-nitroso-5-pyrazolone which can exist both in nitroso (2a) and oxime tautomeric forms (2b). Reduction of the latter using zinc with hydrochloric acid furnished the 4-amino-p-sulphophenyl-3-methyl-5-pyrazolone (3). The diazotization of (3) under careful control of temperature and pH afforded the p-sulphophenyl-3-methyl-5-pyrazolone diazonium salt (4) which was re-crystallized from acidified ethanol to afford crystal suitable for X-ray studies. UV-visible spectrum and cyclic voltammetric studies were also carried out indicating lambda(max) at 420 nm and HOMO-LUMMO energy gap was also calculated (E-g) of 2.95 eV. The molecular and crystal structures of the compound were clarified by single crystal X-ray diffraction indicated that it crystallizes as the sodium salt in the triclinic space group P -1, with the 4-azo-pyrazolone and the sulphophenyl groups being nearly coplanar. To get an insight to the intermolecular interactions in the crystal, a Hirshfeld surface analysis was also carried out.