Spectroscopic and density functional theory studies of 7-hydroxy-3'-methoxyisoflavone: A new isoflavone from the seeds of Indigofera heterantha (Wall).
A new isoflavone 7-hydroxy 3'-methoxyisoflavone (1) is isolated from the seeds of Indigofera heterantha. The structure of this new compound was established using spectroscopic techniques such as ID, 2D NMR, and mass spectrometry. Density functional theory calculations are carried out for the first time for geometric, electronic and spectroscopic properties of 1 (isoflavone). DFT calculations have been performed at B3LYP/6-311G(d,p) level of theory for obtaining geometric and spectroscopic properties of compound 1. The simulated vibrational spectrum of compound 1 at B3LYP/6-311G(d,p) shows nice correlation with the experimental IR spectrum after a scaling factor of 0.973. (1)H and (13)C NMR chemical shifts were calculated using Cramer's re-parameterized function WP04 at 6-311G(d,p) basis set, and show nice correlation with the experimental data. Four conformers were considered for NMR chemical shift calculations. Electronic properties such as band gap, Ionization potential and electron affinities were also simulated for the first time; however, no comparison could be made with the experiment.
Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan; Institute of Chemical Sciences, University of Peshawar, 25120, Pakistan. Electronic address: taj_urrehman81@yahoo.co.uk.
Taj Ur
TU
Rahman
Institute of Chemical Sciences, University of Peshawar, 25120, Pakistan.
Ghias
G
Uddin
Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
Riffat Un
RU
Nisa
Institut für Chemie, Physikalische und Theoretische Chemie, Universität Rostock, Dr.-Lorenz-Weg 1, 18059 Rostock, Germany; Leibniz-Institut für Katalyse an der Universität Rostock e. V., Alebert-Einstein-Strasse 29a, 18059 Rostock, Germany.
Ralf
R
Ludwig
Institute of Chemical Sciences, University of Peshawar, 25120, Pakistan.
Wajiha
W
Liaqat
Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
Tariq
T
Mahmood
Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan.
Ghulam
G
Mohammad
International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan.
M Iqbal
MI
Choudhary
Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan; Department of Chemistry, College of Science, King Faisal University Al Ahsa, 31982, Saudi Arabia. Electronic address: khurshid@ciit.net.pk.
Khurshid
K
Ayub
D029883:Indigofera / Q000737:chemistry*; D007529:Isoflavones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012639:Seeds / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
D007529:Isoflavones
B3LYP/6-311G(d,p); Density functional theory; HOMO–LUMO; I.R; Indigofera heterantha; Isoflavone