1. Synthesis, characterization of flavone, isoflavone, and 2,3-dihydrobenzofuran-3-carboxylate and density functional theory studies
- Author
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Maliha Uroos, Huma Aslam Bhatti, Nizam Uddin, Khalid Mohammed Khan, Khurshid Ayub, Jamshed Iqbal, Mark E. Light, Bibi Saima, Shazia Anjum, and Abdul Hameed
- Subjects
Bond length ,chemistry.chemical_compound ,chemistry ,Computational chemistry ,Stereochemistry ,Regioselectivity ,Density functional theory ,Aromaticity ,Carboxylate ,Carbon-13 NMR ,Spectroscopy ,Flavanone - Abstract
We describe the oxidation of flavanones by employing phenyliodonium diacetate to form the flavone (15), isoflavone (8) and 2,3-dihydrobenzofurane (18) in this study. The oxidative method was found to be regioselective and dependent on the substitution pattern present on the two aromatic rings of the starting flavanone. The structures of products obtained were fully characterized by using IR, 1 H and 13 C NMR spectroscopy and Mass spectrometry. X-ray crystallography further confirms the structures of flavones and isoflavone. The density field theory calculations have also been performed to get more insight about the structures, electronic and spectroscopic properties of synthetic flavonoid derivatives. The geometrical parameters such as bond lengths and angels showed a good correlation with the values obtained through X-ray crystallography. Moreover, the theoretically simulated vibrational and UV-vis spectral values are in agreement with the experimental results.
- Published
- 2015
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