Spectroscopic Evaluation of Azo Coupling Reaction of 4-Aminocoumarin with Aryl Diazonium Chloride Salts: Exclusive Formation of Hydrazone Products

Document Type : Original Article

Authors

Department of Chemistry, Faculty of Science, Lahijan Branch, Islamic Azad University, P.O. Box: 1616, Lahijan, Iran

Abstract

This study used aromatic amines 4-aminoacetanilide, 4-ethyl aniline, 4-butyl aniline, 4-acetyl aniline, and 4-nitro aniline were diazotized using sodium nitride in the presence of hydrochloric acid at 0-5 °C and coupled with 4-amino coumarin to afford five corresponding aryl-azo dyes. The precise structures of the synthesized dyes were determined by using Fourier Transform Infrared (FTIR), proton nuclear magnetic resonance (1H NMR), and carbon nuclear magnetic resonance (13C NMR) spectroscopic techniques. The findings showed that all the dyes have hydrazone tautomeric structures exclusively among the suggested azo and hydrazone structures. Also, there is no evidence for the azo tautomer. In addition, the mass spectrum (MS) of the obtained dyes was recorded and confirmed the proposed structures. The solvatochromic behavior of the dyes was also evaluated in acetic acid, ethanol, chloroform, acetonitrile, dimethyl formamide, and dimethyl sulfoxide. The absorption changes were discussed according to possible electronic transitions in the compounds.

Keywords

References

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Journal of Color Science and Technology
Volume 16, Issue 4 - Serial Number 62
February 2023
Pages 359-372

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