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

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...

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Detalles Bibliográficos
Autores principales: Shabir, Ghulam, Hussain, Ghulam, Saeed, Aamer, Hussain, Tasawwar, Hökelek, Tuncer, Erben, Mauricio Federico, Flörke, Ulrich
Formato: Articulo
Lenguaje:Inglés
Publicado: 2021
Materias:
Química
p-Sulphophenyl-3-methyl-5-pyrazolone
Diazotization
Hirshfeld surface analysis
UV
Energy gap
Crystal structure
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/133880
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-133880
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
p-Sulphophenyl-3-methyl-5-pyrazolone
Diazotization
Hirshfeld surface analysis
UV
Energy gap
Crystal structure
spellingShingle Química
p-Sulphophenyl-3-methyl-5-pyrazolone
Diazotization
Hirshfeld surface analysis
UV
Energy gap
Crystal structure
Shabir, Ghulam
Hussain, Ghulam
Saeed, Aamer
Hussain, Tasawwar
Hökelek, Tuncer
Erben, Mauricio Federico
Flörke, Ulrich
Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
topic_facet Química
p-Sulphophenyl-3-methyl-5-pyrazolone
Diazotization
Hirshfeld surface analysis
UV
Energy gap
Crystal structure
description 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 λ<sub>max</sub> at 420 nm and HOMO-LUMMO energy gap was also calculated (E<sub>g</sub>) 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.
format Articulo
Articulo
author Shabir, Ghulam
Hussain, Ghulam
Saeed, Aamer
Hussain, Tasawwar
Hökelek, Tuncer
Erben, Mauricio Federico
Flörke, Ulrich
author_facet Shabir, Ghulam
Hussain, Ghulam
Saeed, Aamer
Hussain, Tasawwar
Hökelek, Tuncer
Erben, Mauricio Federico
Flörke, Ulrich
author_sort Shabir, Ghulam
title Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
title_short Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
title_full Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
title_fullStr Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
title_full_unstemmed Investigation of stable solid diazonium salt by molecular structure, Hirshfeld surface analysis, optical and electrochemical studies, and applications
title_sort investigation of stable solid diazonium salt by molecular structure, hirshfeld surface analysis, optical and electrochemical studies, and applications
publishDate 2021
url http://sedici.unlp.edu.ar/handle/10915/133880
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