M. Mphahlele, Marole M. Maluleka
Jan 5, 2020
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Journal
Journal of Molecular Structure
Abstract
Abstract The structure of potentially tautomeric 3-aryl-6,8-dibromoquinolin-4(1H)-ones was studied in solution and solid state by means of spectroscopic and single crystal X-ray diffraction (XRD) techniques. Their gas phase geometry was simulated using density functional theory (DFT) methods. Solution phase results using NMR (1H- & 13C-) spectroscopy, ultraviolet (UV) spectrophotometry and liquid chromatography-mass spectrometry (LC-MS) confirmed the structure of the potentially tautomeric derivatives to be 3-arylquinolin-4(1H)-ones (azaisoflavones). Infrared (IR) spectroscopy confirmed their carbonyl nature in the solid state, which is evident in the single crystal X-ray structure of compound 2b, C15H8Br2FNO. The compounds were aromatized and the intermediate 4-chloroquinolines transformed into primary 4-aminoquinolines. The structure and geometry of the 4-anilinoquinoline derivatives were also confirmed in the solid state by means of XRD method. Hirshfeld surface analyses of the crystal structures of quinolin-4(1H)-one 2b and 4-anilino-6,8-dibromoquinoline 4d provided further insight into the role of aromatic-aromatic stacking and intermolecular interactions in the crystal phase.