Molecular structure, FT-IR, vibrational assignments, HOMO-LUMO analysis and molecular docking study of 1-[5-(4-Bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Mary YS 1 , Panicker CY 2 , Sapnakumari M 3 , Narayana B 3 , Sarojini BK 4 , Al-Saadi AA 5 Show all authors , Van Alsenoy C 6 , War JA 7 , Fun HK 8

Affiliations 

  • 1 Department of Physics, Fatima Mata National College, Kollam, Kerala, India
  • 2 Department of Physics, TKM College of Arts and Science, Kollam, Kerala, India. Electronic address: cyphyp@rediffmail.com
  • 3 Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka, India
  • 4 Industrial Chemistry Division, Department of Studies in Chemistry, Mangalore University, Mangalagangotri, Karnataka, India
  • 5 Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia
  • 6 Department of Chemistry, University of Antwerp, B2610 Antwerp, Belgium
  • 7 Department of Chemistry, Dr. H.S. Gour Central University, Sagar, MP, India
  • 8 X-Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Spectrochim Acta A Mol Biomol Spectrosc, 2015 Feb 5;136 Pt B:473-82.
PMID: 25448948 DOI: 10.1016/j.saa.2014.09.060

Abstract

The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 1-[5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone have been investigated experimentally and theoretically using Gaussian09 software package. The title compound was optimized using the HF/6-31G(d) (6D, 7F), B3LYP/6-31G (6D, 7F) and B3LYP/6-311++G(d,p) (5D, 7F) calculations. The B3LYP/6-311++G(d,p) (5D, 7F) results and in agreement with experimental infrared bands. The geometrical parameters are in agreement with XRD data. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. Molecular electrostatic potential was also performed. From the MEP it is evident that the negative charge covers the C=O group and the positive region is over the rings. First hyperpolarizability is calculated in order to find its role in nonlinear optics. Molecular docking studies suggest that the compound might exhibit inhibitory activity against TPII and may act as anti-neoplastic agent.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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