UV–vis, IR and 1H NMR spectroscopic studies of some mono- and bis-azo-compounds based on 2,7-dihydroxynaphthalene and aniline derivatives

The absorption spectra of mono- and bis-azo-derivatives obtained by coupling the diazonium salts of aromatic amines and 2,7-dihydroxynaphthalene have been studied in six organic solvents. The different absorption bands have been assigned and the effect of solvents on the charge transfer band is also...

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Bibliographic Details
Published in:Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2005-12, Vol.62 (4), p.980-986
Main Authors: Issa, Raafat M., Fayed, Tarek A., Awad, Mohammed K., El-Kony, Sanaa M.
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
ASED-MO
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Azo-derivatives
Charge transfer
Dihydroxynaphthalene
Electron Spin Resonance Spectroscopy
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
Naphthols - chemistry
Semi-empirical
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
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Summary:The absorption spectra of mono- and bis-azo-derivatives obtained by coupling the diazonium salts of aromatic amines and 2,7-dihydroxynaphthalene have been studied in six organic solvents. The different absorption bands have been assigned and the effect of solvents on the charge transfer band is also discussed. The diagnostic IR spectral bands and 1H NMR signals are assigned and discussed in relation to molecular structure. Also, semi-empirical molecular orbital calculations using the atom superposition and electron delocalization molecular orbital (ASED-MO) theory have been performed to investigate the molecular and electronic structures of these compounds. According to these calculations, an intramolecular hydrogen bonding is essential for stabilization of such molecules.
ISSN:1386-1425
DOI:10.1016/j.saa.2005.04.018