European Journal of Chemistry 2023, 14(1), 90-98 | doi: https://doi.org/10.5155/eurjchem.14.1.90-98.2386 | Get rights and content

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Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl


Neha Kumari (1) orcid , Ruchika Sharma (2) orcid , Archana Akaram Yadav (3) orcid , Sandeep Ashok Sankpal (4) orcid , Jayakumar Mohan Raj (5) orcid , Saminathan Murugavel (6) orcid , Rajni Kant (7,*) orcid

(1) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(2) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(3) Department of Chemistry, Shivaji University Kolhapur-416004, Maharashtra, India
(4) Department of Chemistry, Shivaji University Kolhapur-416004, Maharashtra, India
(5) Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore-632002, Tamil Nadu, India
(6) Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore-632002, Tamil Nadu, India
(7) Department of Physics, University of Jammu, Jammu Tawi-180006, Jammu and Kashmir, India
(*) Corresponding Author

Received: 13 Dec 2022 | Revised: 10 Jan 2023 | Accepted: 12 Jan 2023 | Published: 31 Mar 2023 | Issue Date: March 2023

Abstract


4-(tert-Butyl)-4-nitro-1,1-biphenyl has been synthesized, and its structure has been characterized by using some spectroscopic and single-crystal X-ray diffraction techniques. It crystallizes in a monoclinic crystal system with space group P21/n and unit cell parameters: a = 6.4478(3) Å, b = 9.2477(4) Å, c = 23.4572(9) Å, β = 95.114(4)°, = 1393.11(10) Å3, Z = 4. The molecular structure has been solved by using the intrinsic phasing method. The crystal structure is stabilized by C-H···O interactions. Computational studies were performed using density functional theory (DFT) and Hartree-Fock (HF) methods. The optimized geometry obtained from DFT and HF in the gas phase was compared with solid-phase experimental data retrieved from single-crystal X-ray diffraction results. Frontier molecular orbitals, such as the HOMO/LUMO energy gap, the molecular electrostatic potential, and Mulliken atomic charges, have been investigated. The HOMO LUMO energy gap of 3.97 eV indicates that the molecule is soft and highly reactive. The Hirshfeld surface analysis and their associated fingerprint plots have been used to quantitatively validate the interactions. Further insilico molecular docking studies have been performed with the molecular target Type-II topoisomerase (PDB ID: 1JIJ) and their results suggest that 4-(tert-butyl)-4-nitro-1,1-biphenyl could be considered an anticancer drug.


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Keywords


X-ray diffraction; Molecular docking; Hartree-Fock method; Single crystal structure; Density functional theory; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.14.1.90-98.2386

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University of Jammu for funding under the Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 project of the Government of India.

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How to cite


Kumari, N.; Sharma, R.; Yadav, A.; Sankpal, S.; Raj, J.; Murugavel, S.; Kant, R. Eur. J. Chem. 2023, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, N.; Sharma, R.; Yadav, A.; Sankpal, S.; Raj, J.; Murugavel, S.; Kant, R. Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl. Eur. J. Chem. 2023, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, N., Sharma, R., Yadav, A., Sankpal, S., Raj, J., Murugavel, S., & Kant, R. (2023). Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl. European Journal of Chemistry, 14(1), 90-98. doi:10.5155/eurjchem.14.1.90-98.2386
Kumari, Neha, Ruchika Sharma, Archana Akaram Yadav, Sandeep Ashok Sankpal, Jayakumar Mohan Raj, Saminathan Murugavel, & Rajni Kant. "Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl." European Journal of Chemistry [Online], 14.1 (2023): 90-98. Web. 31 May. 2023
Kumari, Neha, Sharma, Ruchika, Yadav, Archana, Sankpal, Sandeep, Raj, Jayakumar, Murugavel, Saminathan, AND Kant, Rajni. "Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl" European Journal of Chemistry [Online], Volume 14 Number 1 (31 March 2023)

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