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A Dual Methodology Comprising Experimental and Theoretical Techniques to Study the Synthesis, Characterization, and Supramolecular Assembly of Schiff Bases Derived from Benzocaine

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Abstract

Benzocaine is known for its antibacterial, anticancer, antitumor, and antifungal properties. Herein, a series of three new Schiff bases is synthesized by reacting benzocaine with salicylaldehyde (E4AS), 2,3-dihydroxybenzaldehyde (E4ADH), and 5-chlorosalicylaldehyde (E4ACl). These benzocaine-based Schiff bases were characterized by a variety of spectroscopic methods, including FTIR, NMR, (1H and 13C), and elemental analysis (CHN). Additionally, the single crystal X-ray diffraction method was used to reveal the molecular structures of the derivatives. Solid-state X-ray crystal structures of E4AS and E4ACl adopted enol tautomeric form, whereas keto-tautomeric form was found in E4ADH. The supramolecular assembly of the compounds was probed by Hirshfeld surface analysis. The void analysis was executed to predict the mechanical response of the compounds. Additionally, UV–Vis spectroscopy and molecular docking practices were used to look into the DNA binding abilities of the benzocaine-based Schiff bases. The geometries of the molecules were fully optimized and studied for their electronic structural properties of respective compounds. The frontier molecular orbitals and molecular electrostatic potentials were studied to predict the properties of molecules. The study provides molecular-level intuitions into the synthesis and prospective uses of these Schiff bases in the arena of general and medicinal chemistry.

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Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding the work through group Research Project under grant number GRP/95/44. Khurram Shahzad Munawar, is highly grateful to the Higher Education Commission Pakistan (HEC) for sponsoring this research work.

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Authors and Affiliations

  1. Institute of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Khurram Shahzad Munawar

  2. Department of Chemistry, University of Mianwali, Mianwali, 42200, Pakistan

    Khurram Shahzad Munawar

  3. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Saqib Ali

  4. Department of Chemistry, College of Science, King Khalid University, P.O. Box 9004, 61413, Abha, Saudi Arabia

    Shabbir Muhammad

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

    Muhammad Ashfaq & Muhammad Nawaz Tahir

  6. Nanoscience and Technology Department, National Centre for Physics, QAU-Campus, Islamabad, 45320, Pakistan

    Syed Mustansar Abbas

  7. Institute of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, 64200, Pakistan

    Shabbir Hussain

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  1. Khurram Shahzad Munawar
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Contributions

Conceptualization was contributed by KSM and SA; methodology was contributed by KSM and SH; software was contributed by MNT and SM; data collection, structure solution, refinement, validation were contributed by KSM, MNT, AA, and SM; formal analysis was contributed by KSM and SMA; investigation was contributed by KSM; resources was contributed by KSM and SA; data curation was contributed by KSM; writing—original draft preparation, was contributed by KSM; writing—review and editing, was contributed by KSM and SA; visualization was contributed by SMA; supervision was contributed by SA; project administration was contributed by SA.

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Correspondence to Khurram Shahzad Munawar or Saqib Ali.

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Munawar, K.S., Ali, S., Muhammad, S. et al. A Dual Methodology Comprising Experimental and Theoretical Techniques to Study the Synthesis, Characterization, and Supramolecular Assembly of Schiff Bases Derived from Benzocaine. Arab J Sci Eng 49, 9649–9665 (2024). https://doi.org/10.1007/s13369-024-08934-6

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