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Metal Complexes of a Thiosemicarbazone with Heterocyclic Bases as Coligands: Spectral Characterization, Crystal Structures, DFT and In silico Docking Studies

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Abstract

Copper(II) and zinc(II) complexes, [Cu(esct)(4-pico)] (1), [Zn(esct)(5,5′-dmbipy)]·H2O (2), [Cu(esct)(5,5′-dmbipy)] (3), (where H2esct = 3-ethoxysalicylaldehye-N4-cyclohexylthiosemicarbazone) were synthesized by reacting copper acetate/zinc acetate with the thiosemicarbazone derivative (H2esct) along with heterocyclic bases. The thiosemicarbazone forms doubly deprotonated anions in all the complexes to coordinate via thiolate S, azomethine N and phenolate O atoms. The complexes were characterized by various spectroscopic techniques like infrared, UV–vis, 1H NMR and EPR spectra. The single crystal XRD studies confirmed the structures. All the three complexes got crystallized in triclinic space group P \(\overline{1 }.\) Complexes are found to have four, five and six coordination around the metal center. The importance of van der Waals interactions in them is explained by Hirshfeld surface analysis. We have used Density Functional Theory (DFT) methods and optimized ground states of the studied complexes using the Gaussian 09 package. Electrostatic potential plots of complexes were investigated. Further, docking studies were carried out with various Epidermal Growth Factor Receptor (EGFR) enzymes.

Graphical Abstract

Three mixed ligand Cu(II) and Zn(II) complexes prepared from a thiosemicarbazone showed interesting geometries and structures

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Data Availability

Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Center as CCDC 2158232, 1981316 and 1981315 for complexes 1, 2 and 3 respectively. This may be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Director, CCDC, 12 Union Road, Cambridge, CB2, 1EZ, UK.

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Acknowledgements

SAIF, CUSAT, Kochi, India is acknowledged for single crystal X-ray diffraction measurements. Prof. M. Zeller, Department of Chemistry, Purdue University is acknowledged for his help in refining the SCXRD data. The authors acknowledge IIT Bombay, Mumbai, India for EPR studies.

Funding

NAM is thankful to the UGC, New Delhi, India for providing financial assistance under UGC-SRF (111132/June 2017).

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Authors and Affiliations

  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, Kerala, 682 022, India

    Nimya Ann Mathews & M. R. Prathapachandra Kurup

  2. Department of Chemistry, Bharata Mata College, Thrikkakara, Kochi, Kerala, 682 021, India

    Nimya Ann Mathews

  3. Department of Chemistry, Faculty of Science, Eastern University, Chenkalady, Sri Lanka

    M. Sithambaresan

  4. Health Services Vocational School, Department of Pharmacy, Sivas Cumhuriyet University, 58140, Sivas, Turkey

    Savaş Kaya

  5. Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M’Sik, Hassan II University of Casablanca, 7955, Casablanca, Morocco

    Samir Chtita

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Nimya Ann Mathews, Prathapachandra Kurup, M R, Savas Kaya wrote the manuscript, Samir Chtita performed the computational studies, Sithambaresan M performed investigation of EPR and prepared the EPR and crystal figures.

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Correspondence to M. R. Prathapachandra Kurup.

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10870_2023_1001_MOESM1_ESM.doc

Supplementary file1 (DOC 2293 KB)—Selected bond lengths, bond angles and interactions of the compounds are presented inTables S1-S6. IR spectral assignments, electronic spectral assignments, EPR assignments are provided in Tables S7-S10. Hirshfeld surface analysis attributes are given in Table S11.

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Mathews, N.A., Sithambaresan, M., Kaya, S. et al. Metal Complexes of a Thiosemicarbazone with Heterocyclic Bases as Coligands: Spectral Characterization, Crystal Structures, DFT and In silico Docking Studies. J Chem Crystallogr 54, 99–113 (2024). https://doi.org/10.1007/s10870-023-01001-2

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