Quantum Mechanical Study, Spectroscopic (FT-IR, FT-Raman and UV-Vis) Study, NBO, NLO Analysis and Molecular Docking Studies of 2-Ethoxy-4-(Pyridine-2yliminomethyl)-Phenol

References

• R. H. Lozier, R. A. Bogomolni, and W. Stoeckenius, “Bacteriorhodopsin: A Light-Driven Proton Pump in Halobacterium Halobium,”Biophysical Journal 15, no. 9 (1975): 955–62.
   PubMed Web of Science ®Google Scholar
• A. D. Garnovskii, A. L. Nivorozhkin, and V. I. Minkin, “Ligand Environment and the Structure of Schiff Base Adducts and Tetracoordinated Metal-Chelates,” Coordination Chemistry Reviews 126, no. 1-2 (1993): 1–69.
   Web of Science ®Google Scholar
• J. Costamagna, J. Vargas, R. Latorre, A. Alvarado, and G. Mena, “Coordination Compounds of Copper, Nickel and Iron with Schiff Bases Derived from Hydroxynaphthaldehydes and Salicylaldehydes,” Coordination Chemistry Reviews 119, (1992): 67–88.
   Web of Science ®Google Scholar
• S. R. Salman, S. H. Shawkat, and G. M. Al-Obaidi, “Tautomerism in o-Hydroxy Schiff Bases: Effect of Alkyl Group,” Canadian Journal of Spectroscopy 35 (1990): 25–7.
   Web of Science ®Google Scholar
• O. Atakol, A. Kenar, and M. Kabak, “Some Complexes of Nickel (II) with Ono Type Schiff Bases and Their Monoligand Adducts. Part II,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 27, no. 1 (1997): 29–40.
   Web of Science ®Google Scholar
• C. Temple, Jr G. A. Rener, W. R. Waud, and P. E. Noker, “Antimitotic Agents: Structure-Activity Studies with Some Pyridine Derivatives,” Journal of Medicinal Chemistry 35, no. 20 (1992): 3686–90.
   PubMed Web of Science ®Google Scholar
• M. Huo, Y. Zhang, J. Zhou, A. Zou, D. Yu, Y. Wu, J. Li, and H. Li, “Synthesis and Characterization of Low-Toxic Amphiphilic Chitosan Derivatives and Their Application as Micelle Carrier for Antitumor Drug,” International Journal of Pharmaceutics 394, no. 1-2 (2010): 162–73.
   PubMed Web of Science ®Google Scholar
• P. B. Miniyar and S. J. Makhija, “Synthesis and Antibacterial Activity of 5-Methylpyrazine-2-Carbohydrazide Derivatives,” International Journal of Drug Development and Research 1 (2009): 19–26.
   Google Scholar
• K. Mounika, B. Anupama, J. Pragathi, and C. Gyanakumari, “Synthesis, Characterization, Antifeeding and Insect Growth-Regulating Activities of Cr (III), Mn (II), Fe (III), Co (II), Ni (II) and Cu (II) Complexes with N-Acetylacetonyl-3-Aminocoumarin,” Journal of Scientific Research 2, no. 3 (2010): 513–24.
   Google Scholar
• A. S. Abu-Khadra, R. S. Farag, and A. E. Abdel-Hady, “Synthesis, Characterization and Antimicrobial Activity of Schiff Base (E)-N-(4-(2-Hydroxybenzylideneamino) Phenylsulfonyl) Acetamide Metal Complexes,” American Journal of Analytical Chemistry 7, (2016): 233–45.
   Google Scholar
• R. Miri, N. Razzaghi-Asl, and M. K. Mohammadi, “QM Study and Conformational Analysis of an Isatin Schiff Base as a Potential Cytotoxic Agent,” Journal of Molecular Modeling 19, no. 2 (2013): 727–35.
   PubMed Web of Science ®Google Scholar
• S. M. M. Ali, M. A. K. Azad, M. Jesmin, S. Ahsan, M. M. Rahman, J. A. Khanam, M. N. Islam, and S. M. S. Shahriar, “In Vivo Anticancer Activity of Vanillin Semicarbazone,” Asian Pacific Journal of Tropical Biomedicine 2, no. 6 (2012): 438–42.
   PubMedGoogle Scholar
• M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. J. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, et al., GAUSSIAN 03, Revision E.01 (Wallingford, CT: Gaussian Inc, 2003).
   Google Scholar
• H. B. Schlegel, “Optimization of Equilibrium Geometries and Transition Structures,” Journal of Computational Chemistry 3, no. 2 (1982): 214–8.
   Web of Science ®Google Scholar
• P. Hohenberg and W. Kohn, “Structural Properties of Copper,” Physical Review 136, no. 3B (1964): B864–B871.
   Web of Science ®Google Scholar
• A. D. Becke, “Becke’s Three Parameter Hybrid Method Using the LYP Correlation Functional,” Journal of Chemical Physics98, no. 7 (1993): 5648–52.
   Web of Science ®Google Scholar
• C. Lee, W. Yang, and R. G. Parr, “Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behaviour,” Physical Review B 37, no. 2 (1988): 785–9.
   PubMed Web of Science ®Google Scholar
• A. Frisch, A. B. Nielson, and A. J. Holder, Gaussview User Manual (Pittsburgh, PA: Gaussian Inc, 2000).
   Google Scholar
• R. Ditchfield, “Molecular Orbital Theory of Magnetic Shielding and Magnetic Susceptibility,” Journal of Chemical Physics 56, no. 11 (1972): 5688–91.
   Web of Science ®Google Scholar
• L. Radom and J. A. Pople, “Molecular Orbital Theory of the Electronic Structure of Organic Compounds. IV. Internal Rotation in Hydrocarbons Using a Minimal Slater-Type Basis,” Journal of the American Chemical Society 92, no. 16 (1970): 4786–95.
   Web of Science ®Google Scholar
• J. A. Pople, A. P. Scott, M. W. Wong, and L. Radom, “Scaling Factors for Obtaining Fundamental Vibrational Frequencies and Zero‐Point Energies from HF/6–31G* and MP2/6–31G* Harmonic Frequencies,” Israel Journal of Chemistry 33, no. 3 (1993): 345–50.
   Web of Science ®Google Scholar
• S. Chithiraikumar and M. A. Neelakantan, “Experimental and Theoretical Investigation of a Pyridine Containing Schiff Base: Hirshfeld Analysis of Crystal Structure, Interaction with Biomolecules and Cytotoxicity,” Journal of Molecular Structure 1108 (2016): 654–66.
   Web of Science ®Google Scholar
• A. Teimouri, A. N. Chermahini, K. Taban, and H. A. Dabbagh, “Experimental and CIS, TD-DFT, ab Initio Calculations of Visible Spectra and the Vibrational Frequencies of Sulfonyl Azide-Azoic Dyes,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 72, no. 2 (2009): 369–77.
   PubMed Web of Science ®Google Scholar
• H. A. Dabbagh, A. Teimouri, A. N. Chermahini, and M. Shahraki, “DFT and ab Initio Study of Structure of Dyes Derived from 2-Hydroxy and 2, 4-Dihydroxy Benzoic Acids,” Spectrochimica Acta Part A 69, (2008): 449–59.
   PubMed Web of Science ®Google Scholar
• L. G. Prasad, V. Krishnakumar, and R. Nagalakshmi, “Investigations on the Physicochemical Properties of 2, 4-Dinitrophenol: Efficient Organic Nonlinear Optical Crystal for Frequency Doubling,” Physica B: Condensed Matter 405, no. 6 (2010): 1652–7.
   Web of Science ®Google Scholar
• H. Tanak, “Crystal Structure, Spectroscopy, and Quantum Chemical Studies of (E)-2-[(2-Chlorophenyl) Iminomethyl] -4-Trifluoromethoxyphenol,” The Journal of Physical Chemistry A 115, no. 47 (2011): 13865–76.
   PubMed Web of Science ®Google Scholar
• V. K. Rastogi, M. A. Palafox, R. P. Tanwar, and L. Mittal, “3, 5-Difluorobenzonitrile: Ab Initio Calculations, FTIR and Raman Spectra,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 58, no. 9 (2002): 1987–2004.
   PubMed Web of Science ®Google Scholar
• N. Ramesh Babu, S. Subashchandrabose, M. S. A. Padusha, H. Saleem, V. Manivannan, and Y. Erdoğdu, “Synthesis and Structural Characterization of (E)-N′-((Pyridin-2-yl) Methylene) Benzohydrazide by X-Ray Diffraction, FT-IR, FT-Raman and DFT Methods,” Journal of Molecular Structure 1072 (2014): 84–93.
   Web of Science ®Google Scholar
• N. B. Colthup, L. H. Daly, and S. E. Wiberley, Introduction to Infrared and Raman Spectroscopy (New York: Academic Press Inc, 1964).
   Google Scholar
• L. J. Bellamy, The Infrared Spectra of Complex Molecules 3 (New York: Wiley, 1975).
   Google Scholar
• R. M. Silverstein and F. X. Webster, Spectroscopic Identification of Organic Compound (New York, John Willey & Sons, 1998).
   Google Scholar
• B. H. Stuart, Infrared Spectroscopy: Fundamentals and Applications (London: John Willey & Sons, 2004).
   Google Scholar
• B. C. Smith, Infrared Spectral Interpretation: A Systematic Approach (New York: CRC Press, 1998).
   Google Scholar
• D. Vedal, O. H. Ellestad, P. Klaboe, and G. Hagen, “The Vibrational Spectra of Piperidine and Morpholine and Their N-Deuterated Analogs,” Spectrochimica Acta Part A: Molecular Spectroscopy 32, no. 4 (1976): 877–90.
   Web of Science ®Google Scholar
• N. P. Roeges and J. M. Baas, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures (New York: Wiley, 1994).
   Google Scholar
• D. Lin-Vien, N. B. Colthup, W. G. Fateley, and J. G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules (London: Academic Press: Inc., 1991).
   Google Scholar
• W. B. Tzeng, K. Narayanan, J. L. Lin, and C. C. Tung, “Structures and Vibrations of o-Methylaniline in the S0 and S1 States Studied by ab Initio Calculations and Resonant Two-Photon Ionization Spectroscopy,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 55, no. 1 (1998): 153–62.
   Web of Science ®Google Scholar
• G. Socrates, Infrared and Raman Characteristic Group Frequencies, 3rd ed. (New York: John Wiley & Sons, 2001).
   Google Scholar
• M. Szafran and J. Koput, “Ab Initio and DFT Calculations of Structure and Vibrational Spectra of Pyridine and Its Isotopomers,” Journal of Molecular Structure 565 (2001): 439–48.
   Web of Science ®Google Scholar
• G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives (New York: Halsted Press, 1974).
   Google Scholar
• T. A. Hajam, H. Saleem, M. S. Padhusha, and K. K. Mohammed Ameen. “Synthesis, Quantum Chemical Calculations and Molecular Docking Studies of 2-Ethoxy-4 [(2-Trifluromethyl-Phenylimino) Methyl] Phenol,” Molecular Physics 118 (2020): 1–19.
   Web of Science ®Google Scholar
• V. Krishnakumar, S. Dheivamalar, R. J. Xavier, and V. Balachandran, “Analysis of Vibrational Spectra of 4-Amino-2, 6-Dichloropyridine and 2-Chloro-3, 5-Dinitropyridine Based on Density Functional Theory Calculations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 65, no. 1 (2006): 147–54.
   PubMed Web of Science ®Google Scholar
• D. Michalska, D. C. Bieńko, A. J. Abkowicz-Bieńko, and Z. Latajka, “Density Functional, Hartree − Fock, and MP2 Studies on the Vibrational Spectrum of Phenol,” The Journal of Physical Chemistry 100, no. 45 (1996): 17786–90.
   Web of Science ®Google Scholar
• D. L. Pavia, G. M. Lampman, G. S. Kriz, and J. A. Vyvyan, Introduction to Spectroscopy (USA: Cengage Learning 2008).
   Google Scholar
• L. G. Wade Jr., Organic Chemistry (Upper Saddle River, NJ: Pearson Prentice Hall, 2006).
   Google Scholar
• R. J. Anderson, D. J. Bendell, and P. W. Groundwater, Organic Spectroscopic Analysis (Cambridge: Royal Society of Chemistry Sanderland, 2004).
   Google Scholar
• H. O. Kalinowski, S. Berger, and S. Braun, Carbon-13 NMR Spectroscopy (Chichester: John Wiley & Sons, 1998).
   Google Scholar
• K. Pihlaja and E. Kleinpeter, eds., Carbon-13 Chemical Shifts in Structural and Sterochemical Analysis (Deerfield Beach: VCH Publishers, 1994).
   Google Scholar
• C. James, A. A. Raj, R. Reghunathan, V. S. Jayakumar, and I. H. Joe, “Structural Conformation and Vibrational Spectroscopic Studies of 2, 6‐Bis (p‐N, N‐Dimethyl Benzylidene) Cyclohexanone Using Density Functional Theory,” Journal of Raman Spectroscopy 37, no. 12 (2006): 1381–92.
   Web of Science ®Google Scholar
• A. Pîrnău, V. Chiş, O. Oniga, N. Leopold, L. Szabo, M. Baias, and O. Cozar, “Vibrational and DFT Study of 5-(3-Pyridyl-Methylidene)-Thiazolidine-2-Thione-4-One,” Vibrational Spectroscopy 48, no. 2 (2008): 289–96.
   Web of Science ®Google Scholar
• J. S. Murry and K. Sen, Molecular Electrostatic Potential Concepts and Applications (Amsterdam: Elsevier, 1996).
   Google Scholar
• K. Fukui, “Role of Frontier Orbitals in Chemical Reactions,” Science (New York, N.Y.) 218, no. 4574 (1982): 747–54.
   PubMed Web of Science ®Google Scholar
• B. J. Coe, J. A. Harris, L. A. Jones, B. S. Brunschwig, K. Song, K. Clays, J. Garín, J. Orduna, S. J. Coles, and M. B. Hursthouse, “Syntheses and Properties of Two-Dimensional Charged Nonlinear Optical Chromophores Incorporating Redox-Switchable Cis-Tetraammineruthenium(Ii) Centers,” Journal of the American Chemical Society 127, no. 13 (2005): 4845–59.
   PubMed Web of Science ®Google Scholar
• H. Karaer and I. E. Gumrukcuoglu, “Synthesis and Spectral Characterisation of Novel Azo-Azomethine Dyes,” Turkish Journal of Chemistry 23 (1999): 67–72.
   Web of Science ®Google Scholar
• M. Arivazhagan, R. Kavitha, and V. P. Subhasini, “Conformational Analysis, UV–VIS, MESP, NLO and NMR Studies of 6-Methoxy-1, 2, 3, 4-Tetrahydronaphthalene,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 128 (2014): 701–10.
   PubMed Web of Science ®Google Scholar
• İ. Sıdır, Y. G. Sıdır, M. Kumalar, and E. Taşal, “Ab Initio Hartree–Fock and Density Functional Theory Investigations on the Conformational Stability, Molecular Structure and Vibrational Spectra of 7-Acetoxy-6-(2, 3-Dibromopropyl)-4, 8-Dimethylcoumarin Molecule,” Journal of Molecular Structure 964, no. 1-3 (2010): 134–51.
   Web of Science ®Google Scholar
• V. Balachandran and K. Parimala, “Tautomeric Purine Forms of 2-Amino-6-Chloropurine (N9H10 and N7H10): Structures, Vibrational Assignments, NBO Analysis, Hyperpolarizability, HOMO–LUMO Study Using B3 Based Density Functional Calculations,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012): 340–51.
   PubMed Web of Science ®Google Scholar
• A. Lakshmi and V. Balachandran, “Rotational Isomers, NBO and Spectral Analyses of N-(2-Hydroxyethyl) Phthalimide Based on Quantum Chemical Calculations,” Journal of Molecular Structure 1033 (2013): 40–50.
   Web of Science ®Google Scholar
• S. Ramalingam, M. Karabacak, S. Periandy, N. Puviarasan, and D. Tanuja, “Spectroscopic (Infrared, Raman, UV and NMR) Analysis, Gaussian Hybrid Computational Investigation (MEP Maps/HOMO and LUMO) on Cyclohexanone Oxime,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012): 207–12.
   PubMed Web of Science ®Google Scholar
• Prime (version 3.6) (New York, NY: Schrodinger, LLC, 2014).
   Google Scholar
• R. A. Friesner, R. B. Murphy, M. P. Repasky, L. L. Frye, J. R. Greenwood, T. A. Halgren, P. C. Sanschagrin, and D. T. Mainz, “Extra Precision Glide: Docking and Scoring Incorporating a Model of Hydrophobic Enclosure for Protein − Ligand Complexes,” Journal of Medicinal Chemistry 49, no. 21 (2006): 6177–96.
   PubMed Web of Science ®Google Scholar