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Vol. 37 No. 2 (2025): Vol 37 Issue 2, 2025

Copyright (c) 2025 Xavier S, Bavani C, Kishore G, Pritha P, Sebastian S

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Experimental and Theoretical Analysis of 4-(4-(4,5-Dihydro-5-(4-isopropylphenyl)-1H-pyrazol-3-yl)phenyl)morpholine Molecule: Spectroscopy, NLO, Docking and Reactivity Studies

https://doi.org/10.14233/ajchem.2025.33171
C. Bavani
Department of Physics, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0009-0005-0949-7871
Govindarajalu Kishore
Department of Physics, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0000-0002-8354-7364
Periyasamy Pritha
Department of Physics, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0000-0002-6779-6424
D. Bhakiaraj
Department of Chemistry, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0000-0002-9563-9573
S. Xavier
Department of Physics, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0000-0002-1471-2856
S. Sebastian
Department of Chemistry, St. Joseph’s College of Arts & Science (Autonomous), Cuddalore-607001, India
https://orcid.org/0000-0002-9958-9729

Corresponding Author(s) : S. Xavier

puduvaixavier@gmail.com

Asian Journal of Chemistry, Vol. 37 No. 2 (2025): Vol 37 Issue 2, 2025

Abstract

This study unveils the molecular structural and spectroscopic analysis of 4-(4-(4,5-dihydro-5-(4-isopropylphenyl)-1H-pyrazol-3-yl)-phenyl)morpholine (IPH) to determine its biological behaviour and stability through a DFT study. Theoretical calculations at the B3LYP/6-311G(d,p) level of the basis set and functional group have revealed unique and intriguing insights. Experimental UV-Vis, FT-IR and NMR analyses were carried out, predicting their functional group, mode of vibration and λmax at 300 nm, which also correlated with the DFT studies. The donor-acceptor interactions of molecule have been clarified by executing the natural bond orbital (NBO). Potential energy distribution (PED) was used to identify the vibration mode. To evaluate the 1H and 13C NMR, the gauge independent atomic orbital (GIAO) approach is modified. The electronic transition of the molecule was established by applying the time-dependent density functional theory (TD-DFT) approach. It was found that the theoretical band gap was 4 eV, indicating that the molecule is reactive and stable. By examining the charge distribution and electrostatic potential of molecule, a significant data regarding its active area was revealed. Similarly, the electron-hole distribution was detected and the reactive sites were predicted through the electron localized function (ELF) and localized orbital locator (LOL) studies. The molecular docking was also performed to determine the biological behaviour of the molecules against prostate cancer and the inhibition rate and docking score were also calculated.

Keywords

Pyrazole Optically active Morpholine Acceptor-donor Electron-hole distribution
Bavani, C., Kishore, G., Pritha, P., Bhakiaraj, D., Xavier, S., & Sebastian, S. (2025). Experimental and Theoretical Analysis of 4-(4-(4,5-Dihydro-5-(4-isopropylphenyl)-1H-pyrazol-3-yl)phenyl)morpholine Molecule: Spectroscopy, NLO, Docking and Reactivity Studies. Asian Journal of Chemistry, 37(2), 413–430. https://doi.org/10.14233/ajchem.2025.33171
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References
  1. A. Kumari and R.K. Singh, Bioorg. Chem., 96, 103578 (2020); https://doi.org/10.1016/j.bioorg.2020.103578
  2. F. Arshad, M.F. Khan, W. Akhtar, M.M. Alam, L.M. Nainwal, S.K. Kaushik, M. Akhter, S. Parvez, S.M. Hasan and M. Shaquiquzzaman, Eur. J. Med. Chem., 167, 324 (2019); https://doi.org/10.1016/j.ejmech.2019.02.015
  3. R. Lesyk, J. Med. Sci., 89, 407 (2020); https://doi.org/10.20883/medical.e407
  4. S. El-Assaly, A.E.H.A. Ismail, H. Bary and M. Abouelenein, Curr. Chem. Lett., 10, 309 (2021); https://doi.org/10.5267/j.ccl.2021.3.003
  5. R. Thomas, Y.S. Mary, K.S. Resmi, B. Narayana, B.K. Sarojini, G. Vijayakumar and C. Van Alsenoy, J. Mol. Struct., 1181, 455 (2019); https://doi.org/10.1016/j.molstruc.2019.01.003
  6. S. Sebastian, S. Sylvestre, N. Sundaraganesan, B. Karthikeyan and S. Silvan, Heliyon, 8, e08821 (2022); https://doi.org/10.1016/j.heliyon.2022.e08821
  7. K.A. Abdalkarim, S.J. Mohammed, A.H. Hasan, K.M. Omer, K.H.H. Aziz, F. Paularokiadoss, R.F. Hamarouf, H.Q. Hassan and T. Christopher Jeyakumar, Chem. Phy. Imp., 8, 100402 (2024); https://doi.org/10.1016/j.chphi.2023.100402
  8. S.S. Margreat, S. Ramalingam, H.M. Al-Maqtari, J. Jamalis, S. Sebastian, S. Periandy and S. Xavier, Chem. Data Coll., 33, 100701 (2021); https://doi.org/10.1016/j.cdc.2021.100701
  9. C. Adaikalaraj D. Bhakiaraj R.N. Asha, T.A. Sandosh, S. Manivarman and F. Paularokiadoss, Vietnam J. Chem., 60, 472 (2022); https://doi.org/10.1002/vjch.202100193
  10. H.K. Thabet, A.F. Al-Hossainy and M. Imran, Opt. Mater., 105, 109915 (2020); https://doi.org/10.1016/j.optmat.2020.109915
  11. A. Frisch, Gaussian 09W Reference, Gaussian Inc., Wallingford CT, USA, pp. 1-25 (2009).
  12. H. Kruse, L. Goerigk and S. Grimme, J. Org. Chem., 77, 10824 (2012); https://doi.org/10.1021/jo302156p
  13. M.H. Jamróz. Spectrochim. Acta A: Mol. Biomol. Spectrosc., 114, 220 (2013); https://doi.org/10.1016/j.saa.2013.05.096
  14. R. Tiwari, K. Mahasenan, R. Pavlovicz, C. Li and E. Tjarks, J. Chem. Inf. Mol., 49, 1581 (2009); https://doi.org/10.1021/ci900031y
  15. Z. Ullah, B. Mustafa, H.J. Kim, Y.S. Mary, Y. Shyma Mary and H.W. Kwon, J. Mol. Liq., 357, 119076 (2022); https://doi.org/10.1016/j.molliq.2022.119076
  16. P. Botschwina and J. Flügge, Chem. Phys. Lett., 180, 589 (1991); https://doi.org/10.1016/0009-2614(91)85015-O
  17. J. Demaison, L. Margules and J.E. Boggs, Chem. Phys., 260, 65 (2000); https://doi.org/10.1016/S0301-0104(00)00253-6
  18. S.K. Saha, A. Hens, N.C. Murmu and P. Banerjee, J. Mol. Liq., 215, 486 (2016); https://doi.org/10.1016/j.molliq.2016.01.024
  19. J.M. Ramos, O. Versiane, J. Felcman and C.A. Téllez S., Spectrochim. Acta: Mol. Biomol. Spectrosc., 72, 182 (2009); https://doi.org/10.1016/j.saa.2008.09.026
  20. Y. Kaddouri, F. Abrigach, N. Mechbal, Y. Karzazi, M. El Kodadi, A. Aouniti and R. Touzani, Mater. Today Proc., 13, 956 (2019); https://doi.org/10.1016/j.matpr.2019.04.060
  21. R.R. Pillai, V.V. Menon, Y.S. Mary, S. Armakovic, S.J. Armakovic and C.Y. Panicker, J. Mol. Struct., 1130, 208 (2017); https://doi.org/10.1016/j.molstruc.2016.10.032
  22. S.S. Pathade, V.A. Adole, B.S. Jagdale and T.B. Pawar, J. Mater. Sci. Res. India., 17, 27 (2020); https://doi.org/10.13005/msri.17.special-issue1.05
  23. N. Manju, B. Kalluraya, Asma and M.S. Kumar, J. Mol. Struct., 1193, 386 (2019); https://doi.org/10.1016/j.molstruc.2019.05.049
  24. K. Bhavani, J. Christina Rhoda, M.K. Hossain and C. Karnan, Opt. Mater., 148, 114924 (2024); https://doi.org/10.1016/j.optmat.2024.114924
  25. C. Morell, A. Grand and A. Toro-Labbe, J. Phys. Chem. A, 109, 205 (2005); https://doi.org/10.1021/jp046577a
  26. M. Arivazhagan, S. Manivel, S. Jeyavijayan and R. Meenakshi, Spectrochim. Acta Part A: Mol. Biomol. Spectros., 134, 493 (2015); https://doi.org/10.1016/j.saa.2014.06.108
  27. B.A. Shainyan, N.N. Chipanina, T.N. Aksamentova, L.P. Oznobikhina, G.N. Rosentsveig and I.B. Rosentsveig, Tetrahedron, 66, 8551 (2010); https://doi.org/10.1016/j.tet.2010.08.076
  28. K. Anbukarasi, S. Xavier, J. Jamalis, S. Sebastian, F. Paularokiadoss, S. Periandy and R. Rajkumar, J. Mol. Struct., 1249, 131580 (2022); https://doi.org/10.1016/j.molstruc.2021.131580
  29. K. Anbukarasi, S. Xavier, A.H. Hasan, Y.L. Er, J. Jamalis, S. Sebastian and S. Periandy, Curr. Phys. Chem., 13, 37 (2023); https://doi.org/10.2174/1877946812666220928102954
  30. A. Innasiraj, B. Anandhi, Y. Gnanadeepam, N. Das, F. Paularokiadoss, A.V. Ilavarasi, C.D. Sheela, D.R. Ampasala and T.C. Jeyakumar, J. Mol. Struct., 1265, 133450 (2022); https://doi.org/10.1016/j.molstruc.2022.133450
  31. J. Jamalis, S. Sebastian, S.S. Margreat, K. Subashini, S. Ramalingam, H.M. Al-Maqtari, S. Periandy and S. Xavier, Chem. Data Coll., 28, 100415 (2020); https://doi.org/10.1016/j.cdc.2020.100415
  32. S. Demir, F. Tinmaz, N. Dege and I.O. Ilhan, J. Mol. Struct., 1108, 637 (2016); https://doi.org/10.1016/j.molstruc.2015.12.057
  33. S. Asokan, S. Sebastian, B. Karthikeyan, S. Xavier, R.G. Raman, S. Silvan, S.S. Margreat and R. Sagayaraj, Chem. Phys. Impact, 8, 100497 (2024); https://doi.org/10.1016/j.chphi.2024.100497
  34. S. Sebastian, S. Sylvestre, N. Sundaraganesan, B. Karthikeyan and S. Silvan, Heliyon, 8, e08821 (2022); https://doi.org/10.1016/j.heliyon.2022.e08821
  35. L. Rosenfeld, A. Sananes, Y. Zur, S. Cohen, K. Dhara, S. Gelkop, E. Ben Zeev, A. Shahar, L. Lobel, B. Akabayov, E. Arbely and N. Papo, J. Med. Chem., 63, 7601 (2020); https://doi.org/10.1021/acs.jmedchem.0c00418
  36. W.L. DeLano, CCP4 Newsl. Protein Crystallogr., 40, 82 (2002).
  37. P. Ayaz, D. Andres, D.A. Kwiatkowski, C.C. Kolbe, P. Lienau, G. Siemeister, U. Lücking and C.M. Stegmann, ACS Chem. Biol., 11, 1710 (2016); https://doi.org/10.1021/acschembio.6b00074
  38. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
  39. P. Pritha, G. Kishore, S. Xavier, F. Paularokiadoss, D. Bhakiaraj, S. Periandy, G. Bouzid and S. Ayachi, Mater. Chem. Phys., 326, 129829 (2024); https://doi.org/10.1016/j.matchemphys.2024.129829
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