Synthesis, characterization, computational and biological studies of nitrothiazole incorporated heterocyclic azo dyes

In this work, we have reported four azo dyes having a heterocyclic framework derived from 2-amino-5-nitrothiazole by a traditional diazo-coupling method in an acidic medium using four different coupling components and characterized them by different spectroscopic techniques. The comparative approach...

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Bibliographic Details
Published in:Structural chemistry 2020-08, Vol.31 (4), p.1317-1329
Main Authors: Vinodkumar, Keshavayya, J., Pushpavathi, I., Keerthikumar, C. T., Maliyappa, M. R., Ravi, B. N.
Format: Article
Language:English
Subjects:
Absorption spectra
Antioxidants
Azo dyes
Biological computing
Chemistry
Chemistry and Materials Science
Computer Applications in Chemistry
Coupling
Mathematical analysis
Molecular orbitals
Original Research
Physical Chemistry
Quantum chemistry
Scavenging
Theoretical and Computational Chemistry
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Summary:In this work, we have reported four azo dyes having a heterocyclic framework derived from 2-amino-5-nitrothiazole by a traditional diazo-coupling method in an acidic medium using four different coupling components and characterized them by different spectroscopic techniques. The comparative approach of both the experimental and computational calculations are performed by using DFT/B3LYP at 6-311++G (d, p) basis set with respect to the vibrational and absorption spectra of all the azo dyes. Also, HOMO-LUMO energy and other energy-related global parameters are calculated. The absorption spectra were recorded in the region of 200–700 nm, and the results exhibited a unique absorption in the longer wavelength due to the presence of a nitro group in the moiety as well as solute–solvent interaction. From the quantum chemical calculation values, there is a good correlation that exists between the experimental and computational studies. Furthermore, the antibacterial and antioxidant properties of the azo dyes were evaluated by the disc diffusion method and DPPH assay respectively. The results revealed that all the compounds showed potent inhibitory effect towards the tested pathogenic strains and scavenging activity.
ISSN:1040-0400
1572-9001
DOI:10.1007/s11224-020-01493-0