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Docking, DFT, and structural study of N-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbamothioyl)benzamide

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Abstract

In the current work, we report the synthesis and characterization of N-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbamothioyl)benzamide by reacting 4-aminoantipyrine and benzoylisothiocynate in equimolar ratio. Moreover, the compound was characterized by single crystal XRD analysis. The various intermolecular interactions stabilized the supramolecular assembly, including H-bonding and interaction involving π-ring. Hirshfeld surface analysis was performed in order to probe intermolecular interactions in detail. Interaction energy calculations were conducted to find the type of interaction energy prominent in stabilizing supramolecular assembly. The quantum parameters of the prepared compound were investigated by utilizing the Def2-SVPD basis set in conjunction with the hybrid method of B3LYP. The results revealed quite similarities between the experimental and theoretical calculations. In addition, the HOMO orbitals are located at the hetero atoms, while the LUMO orbitals are located at the benzene ring. In addition, the prepared compound was docked with Ampicillin-CTX-M-15. The results showed good binding interaction between the ligand and the targeted amino acids, with the best binding score of − 5.26 kcal/mol.

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Acknowledgements

The authors are grateful to Tikrit University for its support and acknowledge University of Sargodha, B.O. 40100, Punjab, Pakistan, for their support. Also, the authors from Ardakan University, P.O. Box 184, Ardakan, Iran, and University of Center Florida, USA, are thankful for their support.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Tikrit University, Tikrit, Iraq

    Khalaf A. Jasim, Ahmed S. Faihan & Ahmed S. Al-Janabi

  2. Department of Chemistry, College of Science, University of Sulaimani, Sulaymaniyah, KRG, Iraq

    Nazk Mohammed Aziz

  3. Department of Physics, University of Sargodha, Sargodha, 40100, Pakistan

    Muhammad Ashfaq & Muhammad Nawaz Tahir

  4. Department of Chemical Engineering, Faculty of Engineering, Ardakan University, P.O. Box 184, Ardakan, Iran

    Reza Behjatmanesh-Ardakani

  5. Department of Physics, Faculty of Art and Sciences, Ondokuz Mayis University, Samsun, 55139, Turkey

    Necmi Dege

  6. Nano Science Technology Center, University of Center Florida, Orlando, USA

    Andre J. Gesquiere

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  1. Khalaf A. Jasim
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  2. Nazk Mohammed Aziz
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Contributions

ASF: supervision, review and editing. MA, ND, and MNT: crystallographic analysis. KAJ, NMA, ASA-J, and AJG: conceptualization, methodology, investigation, data curation, writing—review and editing. RB-A: DFT study.

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Correspondence to Ahmed S. Faihan.

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Jasim, K.A., Aziz, N.M., Ashfaq, M. et al. Docking, DFT, and structural study of N-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbamothioyl)benzamide. Struct Chem (2024). https://doi.org/10.1007/s11224-024-02278-5

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