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Synthesis, crystal structure, quantum chemical computation and molecular docking analysis of 1-(4(tert-butyl)-4-methoxy-[1,1-biphenyl]-4-yl) ethenone

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Abstract

The synthesis of 1-(4(tert-butyl)-4-methoxy-[1,1-biphenyl]-4-yl) ethenone (4TBMBE) has been realized in excellent yield by using 4-tert-butyl phenylboronic acid and 1-bromonitrobenzene as the reactants. The single crystals were obtained by solvent-loss technique and its characterization was carried out using the spectral and X-ray diffraction methods. The molecule crystallizes in the monoclinic crystal system with space group (P21/c). There exists one C–H…O intramolecular and an intermolecular C–H···π interaction, besides one π···π (Cg···Cg) interaction responsible for stabilizing the unit cell molecular packing. The density functional theory has been employed to optimize the structure and to carry out the HOMO/LUMO analysis, computation of reactivity parameters, molecular electrostatic potential map and Mulliken population analysis. The Hirshfeld surface analysis probes the existence of various interactions in the crystal structure. Crystal voids analysis confirmed the absence of any significant cavity within the crystal packing. The relative contribution for each contact has been analyzed using the 2D fingerprint plots and their favourability has been validated by the enrichment ratio. The 3D topology of molecular packing has been visualized using energy framework analysis and the nature of molecular interactions existing within the structure has been ascertained using NCI-RDG analysis. The molecular docking investigations have been performed to study the anti-inflammatory action of 4TBMBE against the p38 MAP kinase inhibitor.

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Acknowledgements

Neha Kumari is thankful to the UGC for granting NFSC under the Ministry of Social Justice and Empowerment, Government of India.

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Authors and Affiliations

  1. Chemical Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, Jammu, Jammu & Kashmir, 180006, India

    Neha Kumari & Rajni Kant

  2. Department of Chemistry, Shivaji University Kolhapur, Kolhapur, Maharashtra, 416004, India

    Archana Akaram Yadav & Sandeep Ashok Sankpal

  3. Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore, Tamil Nadu, 632002, India

    Saminathan Murugavel

  4. Department of Physics, C. Abdul Hakeem College of Engineering and Technology, Melvisharam, Tamil Nadu, 632509, India

    Duraiswamy Lakshmanan

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  1. Neha Kumari
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Kumari, N., Yadav, A.A., Sankpal, S.A. et al. Synthesis, crystal structure, quantum chemical computation and molecular docking analysis of 1-(4(tert-butyl)-4-methoxy-[1,1-biphenyl]-4-yl) ethenone. J IRAN CHEM SOC (2024). https://doi.org/10.1007/s13738-024-03032-8

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