REGULAR PAPERNo Access

Synthesis, Spectroscopic Characterization (FT-IR, NMR, UV), NPA, NBO, NLO, Thermochemical Analysis and Molecular Docking Studies of 2-((4-hydroxyphenyl)(piperidin-1-yl)methyl)phenol

Faculty of Art and Science, Department of Chemistry, Bursa Uludag University, Bursa, Turkey

Corresponding author.

https://doi.org/10.1142/S2737416521500150Cited by:6 (Source: Crossref)

Abstract

In this study, a new alkylaminophenol compound was synthesized and characterized by spectroscopic techniques (FT-IR, NMR, UV). The optimized molecular geometry and the vibrational wavenumbers were calculated using density functional theory (DFT) B3LYP/WB97XD and HF methods with 6-311++ G( $d$ $d$ , $p$ $p$ ) basis set. Thus, theoretical data were compared within themselves before comparing with experimental data. The detailed interpretation of the vibrational spectra has been carried out by VEDA program. ¹H-NMR and $^{13}$ $^{13}$ C-NMR chemical shifts of the compound were calculated using GIAO/IEFPCM method in CDCl3. Using time-dependent (TD-DFT) approach electronic properties such as HOMO and LUMO energies, the electronic spectrum of the title compound has been studied and reported. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Linear polarizability, anisotropic linear polarizability and hyperpolarizability values of the title compound were found to be higher than the values of the pNA compound that are used as a standard substance in the NLO analysis. Molecular electrostatic potential (MEP), the thermodynamic properties (heat capacity, entropy and enthalpy) were calculated. Also, to investigate the biological properties of the title compound, molecular docking was done with DNA(PDB ID: 414D). It has been observed that the effective interaction is hydrogen bonds.

Keywords:

References

1. Wang, R.; Xu, J. Selective Alkylation of Aminophenols. Arkivoc 2010, 2010, 293–299. Crossref, Google Scholar
2. Ulaş, Y.; Özkan, A. İ,; Tolan, V. Synthesis of New p-Alkylaminophenol Compounds and Investigation of Their Antimicrobial and Antioxidant Activity. Eur. J. Sci. Technol. 2019, 16, 701–706. Google Scholar
3. Doan, P.; Nguyen, T.; Yli-Harja, O. et al. Effect of Alkylaminophenols on Growth Inhibition and Apoptosis of Bone Cancer Cells. Eur. J. Pharm. Sci. 2017, 107, 208–216. Crossref, Google Scholar
4. Doan, P.; Anufrieva, O.; Yli-Harja, O.; Kandhavelu, M. In Vitro Characterization of Alkylaminophenols-induced Cell Death. Eur. J. Pharmacol. 2018, 820, 229–234. Crossref, Google Scholar
5. Ulaş, Y. Experimental and Theoretical Studies of 2- (naphthalen-1-yl (piperidin-1-yl) methyl)phenol Compound. J. Chem. Soc. Pak. 2020, 42, 574–582. Google Scholar
6. Ulaş, Y. Akıllı Malzemelerin Hazırlanmasında Kullanılacak Amin Türevi Monomerlerin Sentez ve Karakterizasyonu. Eur. J. Sci. Technol. 2019, 16, 242–246. Crossref, Google Scholar
7. Petasis, N. A.; Akritopoulou, I. The Boronic Acid Mannich Reaction: A New Method for the Synthesis of Geometrically Pure Allylamines. Tetrahedron Lett. 1993, 34, 583–586. Crossref, Google Scholar
8. Wu, P.; Givskov, M.; Nielsen, T. E. Reactivity and Synthetic Applications of Multicomponent Petasis Reactions. Chem. Rev. 2019, 119, 11245–11290. Crossref, Google Scholar
9. Liu, Y.; Wang, L.; Sui, Y.; Yu, J. Solvent-free Synthesis of Alkylaminophenols via Petasis Boronic Mannich Reaction in One Pot without Catalysts. Chin. J. Chem. 2010, 28, 2039–2044. Crossref, Google Scholar
10. Chang, Y. M.; Lee, S. H.; Nam, M. H. et al. Petasis Reaction of Activated Quinoline and Isoquinoline with Various Boronic Acids. Tetrahedron Lett. 2005, 46, 3053–3056. Crossref, Google Scholar
11. Portlock, D. E.; Naskar, D.; West, L.; Li, M. Petasis Boronic Acid-Mannich Reactions of Substituted Hydrazines: Synthesis of $α$ $α$ -Hydrazinocarboxylic Acids. Tetrahedron Lett. 2002, 43, 6845–6847, https://doi.org/10.1016/S0040-4039(02)01511-3. Crossref, Google Scholar
12. Neto, I.́; Andrade, J.; Fernandes, A. S. et al. Multicomponent Petasis-borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies. Chem. Med. Chem. 2016, 11, 2015–2023. Crossref, Google Scholar
13. Karrouchi, K.; Fettach, S.; Jotani, M. et al. Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Calculations, Anti-diabetic Activity and Molecular Docking Studies of (E)-N’-(5-bromo-2-hydroxybenzylidene) Isonicotinohydrazide. J. Mol. Struct. 2020, 1221, 128800. Crossref, Google Scholar
14. Ulaş, Y. International Journal of Chemistry and Technology Natural bond orbital (NBO) population analysis and non-linear optical (NLO) properties of 2- (azepan-1-yl (naphthalen-1-yl) methyl) phenol doğrusal olmayan optik (NLO) ö zellikleri. Int. J. Chem. Technol. 2020, 4, 138–145. Crossref, Google Scholar
15. Jamróz, M. H. Vibrational Energy Distribution Analysis (VEDA): Scopes and Limitations. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2013, 114, 220–230. Crossref, Google Scholar
16. Sebastian, S.; Sylvestre, S.; Jayabharathi, J. et al. Study on Conformational Stability, Molecular Structure, Vibrational Spectra, NBO, TD-DFT, HOMO and LUMO Analysis of 3,5-Dinitrosalicylic Acid by DFT Techniques. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2015, 136, 1107–1118. Crossref, Google Scholar
17. Trott, O.; Olson, A. J. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization and Multithreading. J. Comput. Chem. 2010, 31, 455–461. Crossref, Google Scholar
18. Hiremath, S. M.; Suvitha, A.; Patil, N. R. et al. Molecular Structure, Vibrational Spectra, NMR, UV, NBO, NLO, HOMO-LUMO and Molecular Docking of 2-(4, 6-dimethyl-1-benzofuran-3-yl) Acetic Acid (2DBAA): Experimental and Theoretical Approach. J. Mol. Struct. 2018, 1171, 362–374. Crossref, Google Scholar
19. Triki, H.; Nagy, B.; Overgaard, J.; Jensen, F.; Kamoun, S. Structure, DFT Based Investigations on Vibrational and Nonlinear Optical Behavior of a New Guanidinium Cobalt Thiocyanate Complex. Struct. Chem. 2020, 31, 103–114. Crossref, Google Scholar
20. Zacharias, A. O.; Varghese, A.; Akshaya, K. B. et al. DFT, Spectroscopic Studies, NBO, NLO and Fukui Functional Analysis of 1-(1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylidene) Thiosemicarbazide. J. Mol. Struct. 2018, 1158, 1–13. Crossref, Google Scholar
21. Suvitha, A.; Periandy, S.; Gayathri, P. NBO, HOMO-LUMO, UV, NLO, NMR and Vibrational Analysis of Veratrole using FT-IR, FT-Raman, FT-NMR Spectra and HF-DFT Computational Methods. Spectrochim. Acta A. Mol. Biomol. Spectrosc. 2015, 138, 357–369. Crossref, Google Scholar
22. Suvitha, A.; Periandy, S.; Govindarajan, M.; Gayathri, P. Vibrational Analysis using FT-IR, FT-Raman Spectra and HF-DFT Methods and NBO, NLO, NMR, HOMO-LUMO, UV and Electronic Transitions Studies on 2,2,4-Trimethyl Pentane. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 138, 900–912. Crossref, Google Scholar
23. Krishnakumar, V.; Barathi, D.; Mathammal, R. et al. Spectroscopic Properties, NLO, HOMO-LUMO and NBO of Maltol. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 121, 245–253. Crossref, Google Scholar
24. Kucuk, I.; Kaya, Y.; Kaya, A. A. Structural, Spectroscopic (FT-IR, NMR, UV-visible), Nonlinear Optical (NLO), Cytotoxic and Molecular Docking Studies of 4-Nitro-Isonitrosoacetophenone (ninapH) by DFT Method. J. Mol. Struct. 2017, 1139, 308–318. Crossref, Google Scholar
25. Shcherbakov, I. N.; Bulanov, A. O.; Revinskii, Y. V.; Popov, L. D. Conjugated Prototropic and Ring Opening Rearrangements in Schiff Base Derivatives of Formyl Functionalized 2-Oxaindane Series Spiropyran: Synthesis, NMR, IR, UV/Vis, and DFT Study. Struct. Chem. 2019, 30, 1381–1393. Crossref, Google Scholar
26. Nageswari, G.; George, G.; Ramalingam, S.; Govindarajan, M. Molecular Analyses using FT-IR, FT-Raman and UV Spectral Investigation; Quantum Chemical Calculations of Dimethyl Phthalate. J. Mol. Struct. 2019, 1195, 331–343. Crossref, Google Scholar
27. Diwaker, Quantum Mechanical and Spectroscopic (FT-IR, 13C, 1H NMR and UV) Investigations of 2-(5-(4-Chlorophenyl)-3-(pyridin-2-yl)-4,5-Dihydropyrazol-1-yl)Benzo[d]Thiazole by DFT Method. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2014, 128, 819–829. Crossref, Google Scholar
28. Sherin Percy Prema Leela, J.; Hemamalini, R.; Muthu, S.; Al-Saadi, A. A. Spectroscopic Investigation (FTIR spectrum), NBO, HOMO-LUMO Energies, NLO and Thermodynamic Properties of 8-Methyl-N-Vanillyl-6-Nonenamideby DFT Methods. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2015, 146, 177–186. Crossref, Google Scholar
29. Demirciotlu, Z.; Kaştaş, Ç. A.; Büyükgüngör, O. The Spectroscopic (FT-IR, UV-vis), Fukui Function, NLO, NBO, NPA and Tautomerism Effect Analysis of (E)-2-[(2-hydroxy-6-methoxybenzylidene)amino]Benzonitrile. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2015, 139, 539–548. Crossref, Google Scholar
30. Ramachandran, K.; Raja, A.; Mohankumar, V. et al. Experimental and Theoretical Approach of Organic 4,4’-Dimethylbenzophenone (DMBP) Single Crystal for NLO Application. Opt. Laser Technol. 2019, 119, 105640. Crossref, Google Scholar
31. Govindarajan, M.; Karabacak, M. Spectroscopic Properties, NLO, HOMO-LUMO and NBO Analysis of 2,5-Lutidine. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2012, 96, 421–435. Crossref, Google Scholar
32. Ulahannan, R. T.; Panicker, C. Y.; Varghese, H. T. et al. Molecular Structure, FT-IR, FT-Raman, NBO, HOMO and LUMO, MEP, NLO and Molecular Docking Study of 2-[(E)-2-(2-bromophenyl)ethenyl]Quinoline-6-Carboxylic Acid. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2015, 151, 184–197. Crossref, Google Scholar
33. Sinha, L.; Karabacak, M.; Narayan, V. et al. Molecular Structure, Electronic Properties, NLO, NBO Analysis and Spectroscopic Characterization of Gabapentin with Experimental (FT-IR and FT-Raman) Techniques and Quantum Chemical Calculations. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2013, 109, 298–307. Crossref, Google Scholar
34. Pir, H.; Gunay, N.; Tamer, O. et al. Theoretical Investigation of 5-(2-Acetoxyethyl)-6-Methylpyrimidin-2, 4-Dione: Conformational Study, NBO and NLO Analysis, Molecular Structure and NMR Spectra. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2013, 112, 331–342. Crossref, Google Scholar
35. Demircioğlu, Z.; Kaştaş, G.; Kaştaş, Ç. A.; Frank, R. Spectroscopic, XRD, Hirshfeld Surface and DFT Approach (Chemical Activity, ECT, NBO, FFA, NLO, MEP, NPA & MPA) of (E)-4-Bromo-2-[(4-Bromophenylimino)Methyl]-6-Ethoxyphenol. J. Mol. Struct. 2019, 1191, 129–137. Crossref, Google Scholar
36. Guidara, S.; Feki, H.; Abid, Y. Molecular Structure, NLO, MEP, NBO Analysis and Spectroscopic Characterization of 2,5-Dimethylanilinium Dihydrogen Phosphate with Experimental (FT-IR and FT-Raman) Techniques and DFT Calculations. Spectrochim Acta A. Mol. Biomol. Spectrosc. 2014, 133, 856–866. Crossref, Google Scholar
37. Robert, H. M.; Usha, D.; Amalanathan, M. et al. Vibrational Spectral, Density Functional Theory and Molecular Docking Analysis on 4-Nitrobenzohydrazide. J. Mol. Struct. 2020, 1223, 128948. Crossref, Google Scholar
38. Shahana, M. F.; Yardily, A. Synthesis, Spectral Characterization, Dft, and Docking Studies of (4-Amino-2-(Phenylamino) Thiazol-5-Yl)(Thiophene-2-Yl)Methanone and ((4-Amino-2-(4-Chlorophenyl)Amino)Thiazol-5-Yl)(Thiophene-2-Yl)Methanone. J. Struct. Chem. 2020, 61, 1367–1379. Crossref, Google Scholar