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Spectral and Structural Comparisons on Four Pairs of Isomeric 4- and 2-Aminobenzoic Acid Based Aromatic Heterocyclic Dyes

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AbstractFour pairs of isomeric aromatic heterocyclic dyes 1–8, synthesized from the diazotization and subsequent coupling reactions between 4 or 2-aminobenzoic acid as the diazo component and different N-substituted pyridone precursors… Click to show full abstract

AbstractFour pairs of isomeric aromatic heterocyclic dyes 1–8, synthesized from the diazotization and subsequent coupling reactions between 4 or 2-aminobenzoic acid as the diazo component and different N-substituted pyridone precursors as the coupling component, have been characterized and compared including UV–Vis and 1H NMR spectra, X-ray single-crystal structures and related DFT computations. It is noted that X-ray single-crystal diffraction analyses reveal that all of them adopt the same hydrazone-tautomeric form and planar molecular conformation between the pyridine and phenyl rings. However, different intramolecular and intermolecular hydrogen bonding interactions are observed because of the introduction of an electron-withdrawing carboxylic acid group at the ortho or para position in the phenyl ring.Graphical Abstract4-Aminobenzoic acid and 2-aminobenzoic acid have been used as the diazo components to couple with different N-substituted pyridone precursors to produce four pairs of isomeric aromatic heterocyclic dyes, for which 1H NMR spectral, UV–Vis spectral and single-crystal structural comparisons have been made.

Keywords: heterocyclic dyes; structural comparisons; pairs isomeric; four pairs; aminobenzoic acid; aromatic heterocyclic

Journal Title: Journal of Chemical Crystallography
Year Published: 2017

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