Insights into Spectral Elucidations, Reactivity Sites, Invitro Assay, Molecular Docking and Pharmacokinetic Studies of Non-Covalently Bonded 4-Aminobenzoic Acid 4-Nitroaniline

References

• J.M. Aranjani, A. Manuel, H.I.A. Razack, and S.T. Mathew, “Review - COVID-19–Associated Mucormycosis: Evidence-Based Critical Review of an Emerging Infection Burden during the Pandemic’s Second Wave in India,” PLOS Neglected Tropical Diseases 15, no. 11 (2021): e0009921.
   PubMed Web of Science ®Google Scholar
• J.L.R. Tudela and D.W. Denning, “Recovery from Serious Fungal Infections Should Be Realizable for Everyone,” The Lancet. Infectious Diseases 17, no. 11 (2017): 1111–3.
   PubMed Web of Science ®Google Scholar
• Y. Nehela, N.A. Taha, A.A. Elzaawely, T. D. A. Xuan, M. Amin, M. E. Ahmed, and A. El-Nagar, “Benzoic Acid and Its Hydroxylated Derivatives Suppress Early Blight of Tomato (Alternaria Solani) via the Induction of Salicylic Acid Biosynthesis and Enzymatic and Nonenzymatic Antioxidant Defense Machinery,” Journal of Fungi 7, no. 8 (2021): 663–1.
   Web of Science ®Google Scholar
• A. Ozcan, “Investigation of the Effect of Para-Amino Benzoic Acid (PABA) Added Starch-Coated Chemicals on the Printability Properties of Paper,” Journal of Applied Biomaterials & Functional Materials 17, no. 1 (2019): 2280800018816012.
   Web of Science ®Google Scholar
• Z.U. Nisa and T. Akhtar, “Para-Amino Benzoic acid- A Substrate of Immense Significance,” Mini-Reviews in Organic Chemistry 17, no. 6 (2020): 686–700.
   Web of Science ®Google Scholar
• G. Booth, Ullmann’s Encyclopedia of Industrial Chemistry (Weinheim: Wiley-VCH, 2007).
   Google Scholar
• J.S. Al-Otaibi, Y.S. Mary, Y.S. Mary, S.J. Armaković, S. Armaković, C. Van Alsenoy, and H.S. Yathirajan, “Insights into the Reactivity Properties, Docking, DFT and MD Simulations of Orphenadrinium Dihydrogen Citrate in Different Solvents,” Journal of Molecular Liquids 367 (2022): 120583.
   Web of Science ®Google Scholar
• H.A. Al-Ghulikah, A.A. Al-Mutairi, H.M. Hassan, A.A. Emam, Y.S. Mary, Y.S. Mary, S. Armaković, and S.J. Armaković, “Reactivity Properties and Adsorption Behavior of a Triazole Derivative – DFT and MD Simulation Studies,” Journal of Molecular Liquids 341 (2021): 117439.
   Web of Science ®Google Scholar
• A. Silambarasan, P. Rajesh, and P. Ramasamy, “Synthesis, Growth, Structural, Optical and Thermal Properties of an Organic Single Crystal: 4-Nitroaniline 4-Aminobenzoic Acid,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 118, no. 2004 (2014): 24–7.
   PubMedGoogle Scholar
• Y. Zhao, and D. G. Truhlar, “The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals,” Theoretical Chemistry Accounts 120, no. 1-3 (2008): 215–41.
   Web of Science ®Google Scholar
• T.H. Dunning, Jr. and P.J. Hay, Modern Theoretical Chemistry, edited by H.F. Schaefer III, vol. 3 (New York: Plenum, 1977), 1–28.
   Google Scholar
• M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Roobb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, et al., Gaussian 09. Revision A.02 (Wallingford, CT: Gaussian, Inc., 2009).
   Google Scholar
• R. Dennington, T.A. Keith, and J.M. Millam, GaussView (Version 6.1.1) (KS: Semichem Inc., Shawnee Mission, 2019).
   Google Scholar
• T. Lu and F. Chen, “Multiwfn: A Multifunctional Wavefunction analyser,” Journal of Computational Chemistry 33, no. 5 (2012): 580–92.
   PubMed Web of Science ®Google Scholar
• W. Humphrey, A. Dalke, and K. Schulten, “VMD: Visual Molecular Dynamics,” Journal of Molecular Graphics 14, no. 1 (1996): 33–8.
   PubMedGoogle Scholar
• G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson, “Automated Docking Using a Lamarckian Genetic Algorithm and an Empirical Binding Free Energy Function,” Journal of Computational Chemistry 19, no. 14 (1998): 1639–62.
   Web of Science ®Google Scholar
• L. Schrodinger, The PYMOL Molecular Graphics System (Version 1.5) (New York: LLC, 2009).
   Google Scholar
• Kuchitsu (Ed.), Landolt-Bornstein: Group II: Atomic and Molecular Physics Volume 15: Structure Data of Free Polyatomic Molecule (Berlin: Springer-Verlag, 1987).
   Google Scholar
• P. Novak, T. Jednacak, and Z. Mandic (Eds.), Physico Chemical Methods in Drug Discovery and Development, vol. 85 (Zagreb: IAPC Publishing, 2012).
   Google Scholar
• N.D. Abeydeera and C.S. Chow, “Synthesis and Characterization of Modified Nucleotides in the 970 Hairpin Loop of Escherichia coli 16S Ribosomal RNA,” Bioorganic & Medicinal Chemistry 17, no. 16 (2009): 5887–93.
   PubMed Web of Science ®Google Scholar
• H. Arslan, U. Florke, N. Kulcu, and G. Binzet, “The Molecular Structure and Vibrational Spectra of 2- Chloro-N-(Diethylcarbamothioyl)Benzamide by Hartree-Fock and Density Functional Methods,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 68 (2007): 347–1355.
   Web of Science ®Google Scholar
• P. Ewald, “International Tables for X-Ray Crystallography,” Nature 171, no. 4361 (1953): 944–6.
   Google Scholar
• T.J. Beaula, P. Muthuraja, M. Dhandapani, and V.B. Jothy, “Effect of Charge Transfer with Spectral Analysis on the Antibacterial Compound 4-(Dimethyl Amino) Pyridine: 3,5-Dinitrobenzoic Acid: Experimental and Theoretical Perspective,” Journal of Molecular Structure. 1171, no. 2018 (2018): 511–26.
   Google Scholar
• T.L. Huheey and  Cottrell, The Strengths of Chemical Bonds, 2nd ed. (London: Butterworths, 1958).
   Google Scholar
• A.E. Reed and F. Weinhold, “Natural Localized Molecular Orbitals,” Journal of Chemical Physics. 83, no. 4 (1985): 1736–40.
   Web of Science ®Google Scholar
• R.N. Singh, A. Kumar, R.K. Tiwari, P. Rawat, and V.P. Gupta, “A Combined Experimental and Quantum Chemical (DFT and AIM) Study on Molecular Structure, Spectroscopic Properties, NBO and Multiple Interaction Analysis in a Novel Ethyl 4-[2-(Carbamoyl)Hydrazinylidene]-3,5-Dimethyl-1Hpyrrole-2-Carboxylate and Its Dimer,” Journal of Molecular Structure 1035 (2013): 427–40.
   Web of Science ®Google Scholar
• V. Balachandran, S. Rajeswari, and S. Lalitha, “DFT Computations, Vibrational Spectra, Monomer, Dimer, NBO and NMR Analyses of Antifungal Agent: 3,5- Dibromosalicylic Acid,” Journal of Molecular Structure. 1007 (2012): 63–73.
   Web of Science ®Google Scholar
• C.N. Pillai and J. Chellapan, “Effect of Protonation and Hydrogen Bonding on 2, 4, 6-Substitutedpyrimidine and Its Salt Complex- Experimental and Theoretical Evidence,” Journal of Molecular Modeling 20, no. 3 (2014): 2139.
   PubMed Web of Science ®Google Scholar
• S.J. Jenepha Mary, M.U.M. Siddique, S. Pradhan, V. Jayaprakash, and C. James, “Quantum Chemical Insight into Molecular Structure, NBO Analysis of the Hydrogen-Bonded Interactions, Spectroscopic (FT–IR, FT–Raman), Drug Likeness and Molecular Docking of the Novel anti COVID-19 Molecule 2-[(4,6-Diaminopyrimidin-2-yl)Sulfanyl]-N-(4-Fluorophenyl)Acetamide Dimer,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 244 (2021): 118825.
   PubMed Web of Science ®Google Scholar
• G.R. Desiraju, “Crystal Engineering: A Brief Overview,” Journal of Chemical Sciences 122, no. 5 (2010): 667–75.
   Web of Science ®Google Scholar
• R.F.W. Bader, Atoms in Molecules. A Quantum Theory (Oxford: Oxford University Press, 1990).
   Google Scholar
• I. Rozas, I. Alkorta, and J. Elguero, “Behavior of Ylides Containing N, O, and C Atoms as Hydrogen Bond Acceptors,” Journal of the American Chemical Society 122, no. 45 (2000): 11154–61.
   Web of Science ®Google Scholar
• L.F. Matta and R.J. Boyd, An Introduction of the Quantum Theory of Atom in Molecule (Germany: Wiley-VCH Verlag Gmbh, 2007).
   Google Scholar
• M. Alam and D.U. Lee, “Synthesis, Spectroscopic and Computational Studies of 2- (Thiophen-2-yl)-2, 3-Dihydro-1H-Perimidine: An Enzymes Inhibition Study,” Computational Biology and Chemistry 64, no. 2016 (2016): 185–201.
   PubMedGoogle Scholar
• F.C.Y. Pu, A. Ziebell, B.H. Davison, and A.J. Ragauskas, “NMR Characterization of C3H and HCT down-Regulated Alfalfa Lignin,” Bioenergy Research 2 (2009): 198–208.
   Web of Science ®Google Scholar
• A.B. Ahmed, H. Feki, Y. Abid, H. Boughzala, C. Minot, and A. Mlayah, “Crystal Structure, Vibrational Spectra and Theoretical Studies of l -Histidinium Dihydro- Gen Phosphate-Phosphoric Acid,” Journal of Molecular Structure. 920, no. 1–3 (2009): 1–7.
   Web of Science ®Google Scholar
• R.G. Pearson, “Absolute Electronegativity and Hardness: Application to Inorganic Chemistry,” Inorganic Chemistry 83, no. 22 (1986): 8440–1.
   Google Scholar
• R.G. Parr, and J. Pearson, “Absolute Hardness: Companion Parameter to Absolute Electronegativity,” Journal of the American Chemical Society 105, no. 26 (1983): 7512–6.
   Web of Science ®Google Scholar
• T. Bally, S. Nitsche, K. Roth, and E. Haselbach, “Excited States of Polyene Radical Cations: Limitations of Koopmans’ Theorem,” Journal of the American Chemical Society 106, no. 14 (1984): 3927–33.
   Web of Science ®Google Scholar
• A. Esme and S.G. Sagdinc, “Molecular Structures, Spectroscopic (FT–IR, NMR, UV) Studies, NBO Analysis and NLO Properties for Tautomeric Forms of 1,3-Dimethyl-5-(Phenylazo)-6-Aminouracil by Density Functional Method,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 188 (2018): 443–55.
   PubMed Web of Science ®Google Scholar
• M. Arivazhagan, V.P. Subhasini, R. Kavitha, and R. Senthilkumar, “The Spectroscopic (FT-IR, FT-Raman), MESP, First Order Hyperpolarizability, NBO Analysis, HOMO and LUMO Analysis of 1,5-Dimethyl Napthalene by Density Functional Method,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 131, no. 2014 (2014): 636–46.
   PubMedGoogle Scholar
• R. Mohamed Asath, R. Premkumar, T. Mathavan, and A. Milton Franklin Benial, “Spectroscopic and Molecular Docking Studies on N, N-di-Tert-Butoxycarbonyl (Boc)-2-Amino Pyridine: A Potential Bioactive Agent for Lung Cancer Treatment,” Journal of Molecular Structure 1143, no. 2017 (2017): 415–23.
   Google Scholar
• H. Bougherara, R. Kadri, M. Kadri, M. Yekhlef, and A. Boumaza, “Complex of 4-(2-Aminophenyl) 1, 2, 3-Thiadiazole with 2, 3-Dichloro-5, 6- Dicyano-1, 4-Benzoquinone: Experimental Study and Investigation at Different Exchange-Correlation Functionals. DOS, NBO, QTAIM and RDG Analyses,” Journal of Molecular Structure 1223 (2021): 128855–6860.
   Web of Science ®Google Scholar
• J. Mohan, Organic Spectroscopy Principles and Applications (New Delhi: Narosa Publishing House, 2009).
   Google Scholar
• F. De Proft and P. Geerlings, “Conceptual and Computational DFT on the Study of Aromaticity,” Chemical Reviews 101, no. 5 (2001): 1451–64.
   PubMed Web of Science ®Google Scholar
• T.J. Beaula, P. Muthuraja, M. Sethuram, M. Dhandapani, V.K. Rastogi, and V. Bena Jothy, “Biological and Spectral Studies of O-Tolyl Biguanide: Experimental and Theoretical Approach,” Journal of Molecular Structure. 1128 (2017): 290–9.
   Web of Science ®Google Scholar
• J.P. Merrick, D. Moran, and L.J. Radom, “An Evaluation of Harmonic Vibrational Frequency Scale Factors,” Journal of Physical Chemistry A111, no. 45 (2007): 11683–700.
   Google Scholar
• G. Socrates, Infrared and Raman Characteristic Group Frequencies, 3rd edition (UK: John Wiley & sons, Ltd., 2004).
   Google Scholar
• J.P. Jesson and H.W. Thompson, “Vibrational Band Intensities of the C=N Group in Aliphatic Nitriles,” Spectrochimica Acta 13, no. 3 (1958): 217–22.
   Google Scholar
• J. Clarkson, E. Smith, D. Batchelder, D. Smith, and A. Coats, “A Theoretical Study of the Structure and Vibrations of 2,4,6-Trinitrotolune,” Journal of Molecular Structure 648, no. 3 (2003): 203–14.
   Web of Science ®Google Scholar
• D. Lin-Vein, N.B. Colthup, W.G. Fateley, and J.G. Grasselli, The Handbook of Infrared an Raman Characteristic Frequencies of Organic Molecules (San Diego: Academic Press, 1991).
   Google Scholar
• M. Silverstein, G.C. Basseler, and C. Morill, Spectrometric Identification of Organic Compounds (New York: Wiley, 1981).
   Google Scholar
• B.C. Smith, "Spectroscopy: The C=O bond, Part III: Carboxylic acids," Spectroscopy 33, no. 1 (2018): 14–20.
   Web of Science ®Google Scholar
• V. Krishnakumar and V. Balachandran, “FTIR and FT-Raman Spectra, Vibrational Assignments and Density Functional Theory Calculations of 2,6-Dibromo-4-Nitroaniline and 2-(Methylthio)Aniline,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 61, no. 8 (2005): 1811–9.
   PubMed Web of Science ®Google Scholar
• S. Muhammad, S.H. Hassan, A.G. Al-Sehemi, H.A. Shakir, M. Khan, M. Irfan, and J. Iqbal, “Exploring the New Potential Antiviral Constituents of Moringa Oliefera for SARS-COV-2 Pathogenesis: An in Silico Molecular Docking and Dynamic Studies,” Chemical Physics Letters 767 (2021): 138379.
   PubMed Web of Science ®Google Scholar
• T.J. Beaula and C. James, “FT IR, FT-Raman Spectra and Chemical Computations of Herbicide 2-Phenoxy Propionic Acid – A DFT Approach,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 122 (2014): 661–9.
   PubMed Web of Science ®Google Scholar
• B. Silvi and A. Savin, “Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions,” Nature 371, no. 6499 (1994): 683–6.
   Web of Science ®Google Scholar
• F. Rizwana B, J. C. Prasana, S. Muthu, and C.S. Abraham, “Molecular Docking Studies, Charge Transfer Excitation and Wave Function Analyzes (ESP, ELF, LOL) on Valacyclovir: A Potential Antiviral Drug,” Computational Biology and Chemistry 78 (2019): 9–17.
   PubMed Web of Science ®Google Scholar
• H. Jacobsen, “Localized-Orbital Locator (LOL) Profiles of Chemical Bonding,” Canadian Journal of Chemistry 86, no. 7 (2008): 695–702.
   Web of Science ®Google Scholar
• F. Rizwana B, J.C. Prasana, S. Muthu, and C.S. Abraham, “Wavefunction Analysis, Charge Transfer and Molecular Docking Studies on Famciclovir and Entecavir: Potential Anti-Viral Drugs,” Chemical Data Collections 26, no. 1–13 (2020): 100353.
   Google Scholar
• Z. Jia, H. Pang, H. Li, and H. Wang, “A Density Functional Theory Study on Complexation Processes and Intermolecular Interactions of Triptycene-Derived Oxacalixarenes,” Theoretical Chemistry Accounts 138, no. 9 (2019): 113.
   Web of Science ®Google Scholar
• S. Khan, H. Sajid, K. Ayub, and T. Mahmood, “Adsorption Behaviour of Chronic Blistering Agents on Graphdiyne; Excellent Correlation among SAPT, Reduced Density Gradient (RDG) and QTAIM Analyses,” Journal of Molecular Liquids 316 (2020): 113860.
   Web of Science ®Google Scholar
• T. Lu and Q. Chen, “Interaction Region Indicator (IRI): a Very Simple Real Space Function Clearly Revealing Both Chemical Bonds and Weak Interactions,” Chemistry–Methods 1, no. 5 (2021): 231–9.
   Google Scholar
• R.A. Drummond, Aspergillus fumigatus, British Society for Immunology (UK: University of Birmingham, 2021).
   Google Scholar
• M.S. Perumal, S. Sakathibalan, and K. T., “Mucor Spp. – Risk Group (RG) Fungi an Emerging Threat to Human Life,” Just Agriculture Multidisciplinary e-Newsletter 1, no. 10 (2021): 1–4.
   Google Scholar
• J. Araiza, P. Canseco, and A. Bonifaz, “Otomycosis: Clinical and Mycological Study of 97 Cases,” Revue de Laryngologie Otologie Rhinologie 127 (2006): 251–4.
   PubMedGoogle Scholar
• K.W. Loudon, A.P. Coke, J.P. Burnie, A.J. Shaw, B.A. Oppenheim, and C.Q. Morris, “Kitchens as a Source of Aspergillus niger Infection,” The Journal of Hospital Infection 32, no. 3 (1996): 191–8.
   PubMed Web of Science ®Google Scholar
• G.M. Morris and M. Lim-Wilby, “Molecular Docking,” Methods in Molecular Biology 443 (2008): 365–82.
   PubMedGoogle Scholar
• Z. Cournia, B. Allen, and W. Sherman, “Relative Binding Free Energy Calculations in Drug Discovery: Recent Advances and Practical Considerations,” Journal of Chemical Information and Modeling 57, no. 12 (2017): 2911–37.
   PubMed Web of Science ®Google Scholar
• C.A. Lipinski, “Lead-and Drug-like Compounds: The Rule-of-Five Revolution,” Drug Discovery Today Technologies 1, no. 4 (2004): 337–41.
   PubMedGoogle Scholar
• D.E.V. Pires, T.L. Blundell, and D.B. Ascher, “pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph Based Signatures,” Journal of Medicinal Chemistry 58, no. 9 (2015): 4066–72.
   PubMed Web of Science ®Google Scholar
• E. Radchenko, A. Dyabina, V. Palyulin, and N. Zefirov, “Prediction of Human Intestinal Absorption of Drug Compounds,” Russian Chemical Bulletin 65, no. 2 (2016): 576–80.
   Web of Science ®Google Scholar
• D.A. Smith, K. Beaumont, T.S. Maurer, and L. Di, “Clearance in Drug Design: Mini Perspective,” Journal of Medicinal Chemistry 62, no. 5 (2019): 2245–55.
   PubMed Web of Science ®Google Scholar