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Influence of fluorine substitution on the molecular structure, vibrational assignment, Cu–O bond strength and biological properties by comparing copper (II) trifluorobenzoylacetonate and benzoylacetonate complexes

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Abstract

Bis(trifluorobenzoylacetonato) copper(II), Cu(tfba)2, was assayed for isomerism, molecular structure, spectroscopic analysis, and complete vibrational assignment using calculated results from Density Functional Theory (DFT), Natural Bond Orbital (NBO), Atoms-In-Molecules (AIM) analysis at the B3LYP level with 6-311G(d) basis set, and experimental results were obtained via observed vibrational and UV–Vis spectra. To investigate the effects of methyl groups substitution by CF3 on the structure and metal–ligand bond strength of the titled molecules, the structure and vibrational spectra of Cu(tfba)2 were compared with those of bis(benzoylacetonato) copper (II), Cu(bzac)2 using the aforementioned calculation and experimental techniques. Additionally, the calculated values were compared to reported X-ray results. The theoretical and experimental spectroscopic results showed no significant difference between the Cu–O bond strength of Cu(tfba)2 and Cu(bzac)2. In addition, the results of antibacterial activities show that both complexes could be considered potential antibacterial candidates, but Cu(tfba)2 has slightly more antibacterial activity than Cu(bzac)2. Molecular docking studies also indicate that both complexes interact with DNA spontaneously via a minor groove.

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Acknowledgements

The authors are very grateful to Ferdowsi University of Mashhad-Iran for the financial support during this research, Grant No. 45085.

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The authors did not receive support from any organization for the submitted work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Mahnoosh Hakimi-Tabar, Mohammad Vakili, Mohammad Reza Housaindokht, Vahidreza Darugar & Sayyed Faramarz Tayyari

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  1. Mahnoosh Hakimi-Tabar
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  2. Mohammad Vakili
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  3. Mohammad Reza Housaindokht
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  4. Vahidreza Darugar
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  5. Sayyed Faramarz Tayyari
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Contributions

MHT contributed to investigation, data curation, visualization, validation, and writing—original draft. MV contributed to supervision, methodology, writing and editing, responsible for IR, Raman, and UV spectra. MRH contributed to conceptualization, supervision, and editing. VD contributed to writing and editing. SFT contributed to writing—review & editing.

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Correspondence to Mohammad Vakili.

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Hakimi-Tabar, M., Vakili, M., Housaindokht, M.R. et al. Influence of fluorine substitution on the molecular structure, vibrational assignment, Cu–O bond strength and biological properties by comparing copper (II) trifluorobenzoylacetonate and benzoylacetonate complexes. J IRAN CHEM SOC 20, 2949–2961 (2023). https://doi.org/10.1007/s13738-023-02890-y

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