Structural, spectroscopic properties and theoretical studies of (E)-1-(4-Bromophenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one as a potential anti-oxidant agent

ABSTRACT

The new chalcone compound namely (E)-1-(4-Bromophenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one (C₁₈H₁₇BrO₄) is crystallized in the monoclinic crystal system of P2₁/c space group. The unit cell dimensions are: a  =  8.0753 (10) Å, b  =  21.873 (3) Å, c  =  9.3362 (12) Å, α = 90°, β  =  99.369 (2), γ = 90° and Z  =  4. The single crystal was grown using slow evaporation solution growth technique. The newly synthesized compound was characterized by using IR, ¹H- and ¹³C-NMR, UV-Vis and single crystal X-ray diffraction analyses. Quantum chemical method of Density Functional Theory (DFT) with B3LYP/6-311++G(d,p) has been employed to study the structural and spectral properties of the compound. The electronic absorption spectrum was calculated using the time dependent functional theory (TDDFT) method. The most stable conformer of the title chalcone is identified from the computational results. Hirshfeld surface analysis with fingerprint plots has been used as a graphical tool for visualization and understanding of intermolecular interactions. Intermolecular C‒H····O interaction observed stabilize the crystal structure, forming an infinite one dimensional column. The effect of this intermolecular interaction in the solid state can be seen in the difference between the experimental and the theoretically optimized geometrical parameters. The crystal is transparent in the entire visible region and absorptive in the UV region. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecule has been obtained by mapping electron potential (MEP). The other molecular properties like charge transfer are explain using Mulliken population analysis. The antioxidant test indicated that the 2,3,4-trimethoxy substitution on the bromide chalcone to be one of the favorable modification to enhance its metal chelating activity.

KEYWORDS:

• Anti-oxidant activities
• chalcone
• DFT calculations
• molecular structure
• spectroscopic analyses

Funding

The authors thank the Universiti Sains Malaysia (USM) and the Malaysian Government for the research facilities and the Research Universiti Grant No. 1001/PBIOLOGI/813049, Short Term Grant No. 304/PFIZIK/6313336 and the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711572, respectively to conduct this work. DAZ thanks to Malaysian Government for the My Brain15 scholarship.

Supplementary material

CCDC 1013204 contains the supplementary crystallographic data for this article. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.