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Research Articles

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

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Pages 1722-1744 | Received 28 Sep 2022, Accepted 14 Apr 2023, Published online: 02 May 2023

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.
  • 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.
  • 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.
  • 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.
  • 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.
  • G. Booth, Ullmann’s Encyclopedia of Industrial Chemistry (Weinheim: Wiley-VCH, 2007).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • R. Dennington, T.A. Keith, and J.M. Millam, GaussView (Version 6.1.1) (KS: Semichem Inc., Shawnee Mission, 2019).
  • T. Lu and F. Chen, “Multiwfn: A Multifunctional Wavefunction analyser,” Journal of Computational Chemistry 33, no. 5 (2012): 580–92.
  • W. Humphrey, A. Dalke, and K. Schulten, “VMD: Visual Molecular Dynamics,” Journal of Molecular Graphics 14, no. 1 (1996): 33–8.
  • 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.
  • L. Schrodinger, The PYMOL Molecular Graphics System (Version 1.5) (New York: LLC, 2009).
  • Kuchitsu (Ed.), Landolt-Bornstein: Group II: Atomic and Molecular Physics Volume 15: Structure Data of Free Polyatomic Molecule (Berlin: Springer-Verlag, 1987).
  • P. Novak, T. Jednacak, and Z. Mandic (Eds.), Physico Chemical Methods in Drug Discovery and Development, vol. 85 (Zagreb: IAPC Publishing, 2012).
  • 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.
  • 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.
  • P. Ewald, “International Tables for X-Ray Crystallography,” Nature 171, no. 4361 (1953): 944–6.
  • 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.
  • T.L. Huheey and  Cottrell, The Strengths of Chemical Bonds, 2nd ed. (London: Butterworths, 1958).
  • A.E. Reed and F. Weinhold, “Natural Localized Molecular Orbitals,” Journal of Chemical Physics. 83, no. 4 (1985): 1736–40.
  • 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.
  • 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.
  • 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.
  • 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.
  • G.R. Desiraju, “Crystal Engineering: A Brief Overview,” Journal of Chemical Sciences 122, no. 5 (2010): 667–75.
  • R.F.W. Bader, Atoms in Molecules. A Quantum Theory (Oxford: Oxford University Press, 1990).
  • 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.
  • L.F. Matta and R.J. Boyd, An Introduction of the Quantum Theory of Atom in Molecule (Germany: Wiley-VCH Verlag Gmbh, 2007).
  • 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.
  • 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.
  • 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.
  • R.G. Pearson, “Absolute Electronegativity and Hardness: Application to Inorganic Chemistry,” Inorganic Chemistry 83, no. 22 (1986): 8440–1.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • J. Mohan, Organic Spectroscopy Principles and Applications (New Delhi: Narosa Publishing House, 2009).
  • F. De Proft and P. Geerlings, “Conceptual and Computational DFT on the Study of Aromaticity,” Chemical Reviews 101, no. 5 (2001): 1451–64.
  • 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.
  • 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.
  • G. Socrates, Infrared and Raman Characteristic Group Frequencies, 3rd edition (UK: John Wiley & sons, Ltd., 2004).
  • 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.
  • 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.
  • 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).
  • M. Silverstein, G.C. Basseler, and C. Morill, Spectrometric Identification of Organic Compounds (New York: Wiley, 1981).
  • B.C. Smith, "Spectroscopy: The C=O bond, Part III: Carboxylic acids," Spectroscopy 33, no. 1 (2018): 14–20.
  • 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.
  • 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.
  • 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.
  • B. Silvi and A. Savin, “Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions,” Nature 371, no. 6499 (1994): 683–6.
  • 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.
  • H. Jacobsen, “Localized-Orbital Locator (LOL) Profiles of Chemical Bonding,” Canadian Journal of Chemistry 86, no. 7 (2008): 695–702.
  • 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.
  • 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.
  • 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.
  • 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.
  • R.A. Drummond, Aspergillus fumigatus, British Society for Immunology (UK: University of Birmingham, 2021).
  • 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.
  • J. Araiza, P. Canseco, and A. Bonifaz, “Otomycosis: Clinical and Mycological Study of 97 Cases,” Revue de Laryngologie Otologie Rhinologie 127 (2006): 251–4.
  • 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.
  • G.M. Morris and M. Lim-Wilby, “Molecular Docking,” Methods in Molecular Biology 443 (2008): 365–82.
  • 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.
  • C.A. Lipinski, “Lead-and Drug-like Compounds: The Rule-of-Five Revolution,” Drug Discovery Today Technologies 1, no. 4 (2004): 337–41.
  • 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.
  • 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.
  • 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.

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