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

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Abstract

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 λmax at 420 nm and HOMO-LUMMO energy gap was also calculated (Eg) 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.

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Funding

The authors are grateful to Quaid-I-Azam University, Islamabad, Pakistan for providing research funds.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-I-Azam University, Islamabad, 45320, Pakistan

    Ghulam Shabir & Aamer Saeed

  2. Institute of Chemistry, University of the Punjab, Lahore, Pakistan

    Ghulam Hussain

  3. Department of Physics, Hacettepe University, 06800, Beytepe-Ankara, Turkey

    Tuncer Hökelek

  4. CEQUINOR (UNLP, CONICET-CCT La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 1465, La Plata, 1900, República Argentina

    Mauricio F. Erben

  5. Department Chemie, Fakultät Fur Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, 33098, Paderborn, Germany

    Ulrich Flörke

  6. Department of Chemistry, Government College University, Faisalabad, Pakistan

    Tasawwar Hussain

Authors
  1. Ghulam Shabir
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  2. Ghulam Hussain
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  3. Aamer Saeed
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  4. Tasawwar Hussain
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  5. Tuncer Hökelek
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  6. Mauricio F. Erben
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  7. Ulrich Flörke
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Contributions

Ghulam Shabir: synthesis and interpretation, electrochemical studies. Ghulam Hussain: synthesis and data collection. Aamer Saeed: conceptualization, manuscript writing. Tasawwar Hussain: writing draft, optical studies. Tuncer Hökelek: Hirshfeld surface analysis. Mauricio F. Erben: optical studies. Ulrich Flörke: crystallography.

Corresponding author

Correspondence to Aamer Saeed.

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Research highlights

1. Solid stable diazonium salt, synthetic precursor towards acid Azo dyes

2. Triclinic geometry with coplanar 4-azo-pyrazolone and the sulphophenyl groups

3. Absorption maximum (λmax) in visible range at 420 nm

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Shabir, G., Hussain, G., Saeed, A. et al. Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications. J Mol Model 27, 296 (2021). https://doi.org/10.1007/s00894-021-04910-1

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  • DOI: https://doi.org/10.1007/s00894-021-04910-1

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