title: Spectroscopic and density functional theory studies of 5,7,3',5'-tetrahydroxyflavanone from the leaves of Olea ferruginea.
abstract: 5,7,3',5'-Tetrahydroxyflavanone (1) was isolated from the leaves of Olea ferruginea and a theoretical model was developed for obtaining the electronic and spectroscopic properties of 1. The geometric and electronic properties were calculated at B3LYP/6-311 G (d, p) level of Density Functional Theory (DFT). The theoretical data was in good agreement with the experimental one. The optimized geometric parameters of compound 1 were calculated for the first time. The theoretical vibrational frequencies of 1 were found to correlate with the experimental IR spectrum after a scaling factor of 0.9811. The UV and NMR spectral data computed theoretically were in good agreement with the experimental data. Electronic properties of the compound i.e., ionization potential (IP), electron affinity (EA), coefficients of HOMO and LUMO were estimated computationally for the first time which can be used to explain its antioxidant as well as other related activities and more active sites on it. The intermolecular interactions and their effects on IR frequencies, electronic and geometric parameters were simulated using water molecule as a model for hydrogen bonding with flavonoid hydroxyl groups.
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
authors.forename: Muhammad Ali
authors.initials: MA
authors.lastname: Hashmi
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan. Electronic address: afsarhej@yahoo.com.
authors.forename: Afsar
authors.initials: A
authors.lastname: Khan
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan; Department of Chemistry, College of Science, King Faisal University, Al-Hafouf 31982, Saudi Arabia.
authors.forename: Khurshid
authors.initials: K
authors.lastname: Ayub
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
authors.forename: Umar
authors.initials: U
authors.lastname: Farooq
mesh_terms: D044950:Flavanones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D031658:Olea / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry*; D013055:Spectrophotometry, Infrared / Q000379:methods
chemical_list: C479303:5,7,3',5'-tetrahydroxyflavanone; D044950:Flavanones
keywords: B3LYP/6-311 G (d, p); DFT; Density functional theory; Olea ferruginea; Tetrahydroxyflavanone