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A DFT study of structural-stability, Mulliken charges, MEP, FMO, and NLO properties of trans alkenyl substituted chalcones conformers: theoretical study

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Abstract

In this research, density functional theory (DFT) was used with the B3LYP functional hybrid and the 6–311++G(d,p) basis set for the geometry optimization. First, the findings of the scanning for the potential energy surface (PES) for the vinyl chalcone (VC) have shown that the s-cis conformer was more stable than the s-trans conformer. The data also indicated that 1-butenyl chalcone (1-BC) is the most stable conformer and significantly improves the stability of unsubstituted chalcone (CA). VC was shown to be the least stable conformer. Second, the results were further supported by measuring the thermodynamic parameters thermal energy (TE), entropy (S), and heat capacity (Cv). TE, S, and Cv increased with the stability of conformer and decreased with the increased polarity of the solvent. Finally, the computed C = O stretching vibrations indicated that divinyl chalcone (DVC) causes the largest shift in the peak center of the C = O stretching vibrations of CA by a deviation 4.79 cm−1 in the gas phase and 5.75 cm−1 in n-hexane. The UV–Vis spectra for the studied conformers were analyzed by time-dependent density functional theory (TD-DFT) and the results displayed that the most planar conformers DVC and 1-BC have the highest values of maximum wavelength (λmax). The results shown that CA possesses the highest electronegativity (χ) while trans propenyl chalcone (E-PC) possesses the lowest electronegativity. The dipole moment (µ), polarizability (α), and first hyper polarizability (β) were seen to increase with the π-conjugation and solvent polarity. E-PC, 1-BC, and DVC constituted the highest magnitudes of µ, α, and β.

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Acknowledgements

The author would like to thank Prof. Dr Ghazwan F.Fathil for the support provided to carry out this work.

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  1. Department of Chemistry, College of Science, University of Duhok, Duhok, Kurdistan Region, Iraq

    Haval A. Hussein

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  1. Haval A. Hussein
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Correspondence to Haval A. Hussein.

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Hussein, H.A. A DFT study of structural-stability, Mulliken charges, MEP, FMO, and NLO properties of trans alkenyl substituted chalcones conformers: theoretical study. Struct Chem 34, 2201–2223 (2023). https://doi.org/10.1007/s11224-023-02139-7

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