2. Academic Validation
  3. Spectroscopic and density functional theory studies of 7-hydroxy-3'-methoxyisoflavone: A new isoflavone from the seeds of Indigofera heterantha (Wall)

Spectroscopic and density functional theory studies of 7-hydroxy-3'-methoxyisoflavone: A new isoflavone from the seeds of Indigofera heterantha (Wall)

  • Spectrochim Acta A Mol Biomol Spectrosc. 2015 Sep 5:148:375-81. doi: 10.1016/j.saa.2015.04.018.
Taj Ur Rahman 1,  Ghias Uddin 2,  Riffat Un Nisa 3,  Ralf Ludwig 4,  Wajiha Liaqat 2,  Tariq Mahmood 3,  Ghulam Mohammad 5,  M Iqbal Choudhary 6,  Khurshid Ayub 7
Affiliations

Affiliations

  • 1 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.
  • 2 Institute of Chemical Sciences, University of Peshawar, 25120, Pakistan.
  • 3 Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.
  • 4 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.
  • 5 Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan.
  • 6 International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan.
  • 7 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.
PMID: 25913137 DOI: 10.1016/j.saa.2015.04.018
Abstract

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.

Keywords

B3LYP/6-311G(d,p); Density functional theory; HOMO–LUMO; I.R; Indigofera heterantha; Isoflavone.

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