Investigation on the stability of the Enol Tautomer of Favipiravir and its derivatives by DFT, QTAIM, NBO, NLO and ¹H-NMR

References

• Furuta Y, Gowen BB, Takahashi K, et al. Favipiravir (T-705), a novel viral RNA polymerase inhibitor. Antiviral Res. 2013;100:446. doi:10.1016/j.antiviral.2013.09.015
   PubMed Web of Science ®Google Scholar
• Smyk JM, Majewska A. Favipiravir in the battle with respiratory viruses. Mini Rev Med Chem. 2022;22:2224–2236. doi:10.2174/1389557522666220218122744
   PubMed Web of Science ®Google Scholar
• Konstantinova ID, Andronova VL, Fateev IV, et al. Favipiravir and Its structural analogs: antiviral activity and synthesis methods. Acta Naturae. 2022;14:16–38. doi:10.32607/actanaturae.11652
   PubMed Web of Science ®Google Scholar
• Shiraki K, Daikoku T. Favipiravir, an anti-influenza drug against life-threatening RNA virus infections. Pharmacol. Ther. 2020;209:107512. doi:10.1016/j.pharmthera.2020.107512
   PubMed Web of Science ®Google Scholar
• Furuta Y, Komeno T, Nakamura T. Favipiravir (T-705), a broad spectrum inhibitor of viral RNA polymerase. Proc Jpn Acad Ser B. 2017;93:449.
   PubMed Web of Science ®Google Scholar
• Furuta Y, Takahashi K, Shiraki K, et al. T-705 (favipiravir) and related compounds: novel broad-spectrum inhibitors of RNA viral infections. Antiviral Res. 2009;82:95–102. doi:10.1016/j.antiviral.2009.02.198
   PubMed Web of Science ®Google Scholar
• Beak P, Fry FS. Equilibrium between 2-hydroxypyridine and 2-pyridone in the gas phase. J Am Chem Soc 1973;95:1700–1702. doi:10.1021/ja00786a078
   Web of Science ®Google Scholar
• Katritzky A, Elguero J. The Tautomerism of heterocycles. Advances in Heterocyclic Chemistry. New York: Academic Press; 1976.
   Google Scholar
• Elguero J, Katritzky AR, Denisko OV. Prototropic tautomerism of heterocycles: heteroaromatic tautomerism-general overview and methodology. Adv Heterocycl Chem. 2000;76:1–84. doi:10.1016/S0065-2725(00)76003-X
   Web of Science ®Google Scholar
• Schulman SG, Underberg WJ. Excitation wavelength dependence of prototropic dissociation and tautomerism of salicylamide in the lowest excited singlet state. Photochem Photobiol 1979;29:937–941. doi:10.1111/j.1751-1097.1979.tb07795.x
   Web of Science ®Google Scholar
• Woolfe GJ, Thistlethwaite PJ. Excited-state prototropic reactivity in salicylamide and salicylanilide. J Am Chem Soc 1980;102:6917–6923. doi:10.1021/ja00543a003
   Web of Science ®Google Scholar
• Nishiya T, Yamauchi S, Hirota N, et al. Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxya-cetophenone, salicylamide, and related molecules. J Phys Chem. 1986;90:5730–5735. doi:10.1021/j100280a053
   Web of Science ®Google Scholar
• Kramer HA. Tautomerism by hydrogen transfer in salicylates, triazoles, and oxazoles. Stud Org Chem. 1990;40:654–684.
   Google Scholar
• Sobczyk L, Chudoba D, Tolstoy PM, et al. Some brief notes on theoretical and experimental investigations of intramolecular hydrogen bonding. Molecules. 2016;21:1657. doi:10.3390/molecules21121657
   PubMed Web of Science ®Google Scholar
• Antonov L. Favipiravir tautomerism: a theoretical insight. Theor Chem Acc. 2020;139:145.
   PubMed Web of Science ®Google Scholar
• Deneva V, Slavova S, Kumanova A, et al. Favipiravir—tautomeric and complexation properties in solution. Pharmaceuticals. 2023;16:45. doi:10.3390/ph16010045
   Web of Science ®Google Scholar
• Albarakati R, Al-Qurashi O, Safi Z, et al. A dispersion-corrected DFT calculation on encapsulation of favipiravir drug used as antiviral against COVID-19 into carbon-, boron-, and aluminum-nitride nanotubes for optimal drug delivery systems combined with molecular docking simulations. Struct Chem. 2023: 1. doi:10.1007/s11224-023-02182-4
   PubMed Web of Science ®Google Scholar
• Umar Y. Theoretical studies of the rotational and tautomeric states, electronic and spectroscopic properties of favipiravir and its structural analogues: a potential drug for the treatment of COVID-19. J Taibah Univ Sci. 2020;14:1613–1625. doi:10.1080/16583655.2020.1848982
   Web of Science ®Google Scholar
• Jena N. Role of different tautomers in the base-pairing abilities of some of the vital antiviral drugs used against COVID-19. Phys Chem Chem Phys. 2020;22:28115–28122. doi:10.1039/D0CP05297C
   PubMed Web of Science ®Google Scholar
• da Silva G. Protonation, tautomerism, and base pairing of the antiviral favipiravir (T-705). 2020.
   Google Scholar
• Kavitha N, Alivelu M. Favipiravir Tautomers: a novel investigation of quantum chemical, QTAIM, RDG – NCI, bioactivity, and molecular docking STUDIES. Int J Sci Res Sci Technol. 2021;8:668.
   Google Scholar
• Assis LC, de Castro AA, de Jesus JPA, et al. Theoretical insights into the effect of halogenated substituent on the electronic structure and spectroscopic properties of the favipiravir tautomeric forms and its implications for the treatment of COVID-19. La Porta, RSC Advances. 2021;11:35228. doi:10.1039/D1RA06309J
   PubMed Web of Science ®Google Scholar
• Jeffrey GA, Saenger W. Hydrogen bonding in proteins. In: Hydrogen bonding in biological structures. Berlin: Springer; 1991. p. 351–393.
   Google Scholar
• Jeffrey GA, Saenger W. The importance of hydrogen bonds. In: Hydrogen bonding in biological structures. Berlin: Springer; 1991. p. 3–14.
   Google Scholar
• Bader RFW. A quantum theory of molecular structure and its applications. Chem Rev 1991;91:893–928. doi:10.1021/cr00005a013
   Web of Science ®Google Scholar
• Bader RF. Atom in molecules a quantum theory (AIM). 1990.
   Google Scholar
• Bader RF. Atoms in molecules. Acc Chem Res. 1985;18:9.
   Web of Science ®Google Scholar
• Afonin AV, Vashchenko AV. Benchmark calculations of intramolecular hydrogen bond energy based on molecular tailoring and function-based approaches: developing hybrid approach. Int J Quantum Chem. 2019;119:e26001. doi:10.1002/qua.26001
   Web of Science ®Google Scholar
• Grabowski SJ. Intramolecular hydrogen bond energy and its decomposition—O–H···O interactions. Crystals (Basel). 2021;11:5. doi:10.3390/cryst11010005
   Web of Science ®Google Scholar
• Deshmukh MM, Gadre SR. Molecular tailoring approach for the estimation of intramolecular hydrogen bond energy. Molecules. 2021;26:2928. doi:10.3390/molecules26102928
   PubMed Web of Science ®Google Scholar
• Hammami F, Issaoui N. A DFT study of the hydrogen bonded structures of pyruvic acid–water complexes. Front Phys. 2022;10:901736. doi:10.3389/fphy.2022.901736
   Web of Science ®Google Scholar
• Safi ZS. Tautomeric study of neutral, protonated and deprotonated isorhodanine based on high level density functional theory. Orient J Chem. 2016;2:2371–2381.
   Google Scholar
• Saraf SH, Ghiasi R. Quantum theory of atoms in molecules, electron localization function, and localized-orbital locator investigations on trans-(NHC)PtI2(para-NC5H4X) complexes. J Chem Res. 2020;44:482–486. doi:10.1177/1747519820907243
   Web of Science ®Google Scholar
• Mata I, Alkorta I, Molins E, et al. Universal features of the electron density distribution in hydrogen-bonding regions: a comprehensive study involving H⋅⋅⋅X (X=H, C, N, O, F, S, Cl, π) interactions. Chem A Eur J. 2010;16:2442–2452. doi:10.1002/chem.200901628
   PubMed Web of Science ®Google Scholar
• Tang T-H, Deretey E, Knak Jensen S, et al. Hydrogen bonds: relation between lengths and electron densities at bond critical points. Eur Phys J D-Atom, Mole, Opt Plasma Phys. 2006;37:217.
   Google Scholar
• Espinosa E, Molins E, Lecomte C. Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem Phys Lett. 1998;285:170–173. doi:10.1016/S0009-2614(98)00036-0
   Web of Science ®Google Scholar
• Tahir MN, Mirza SH, Khalid M, et al. Synthesis, single crystal analysis and DFT based computational studies of 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrim idin-1-ium 3,4,5-trihydroxybenzoate -methanol (DETM). J Mol Struct. 2019;1180:119–126. doi:10.1016/j.molstruc.2018.11.089
   Web of Science ®Google Scholar
• Shafiq I, Amanat I, Khalid M, et al. Influence of azo-based donor modifications on nonlinear optical amplitude of D-π-A based organic chromophores: A DFT/TD-DFT exploration. Synth Met. 2023;297:117410), doi:10.1016/j.synt-hmet.2023.117410
   Web of Science ®Google Scholar
• Safi ZS, Wazzan N. Benchmark calculations of proton affinity and gas-phase basicity using multilevel (G4 and G3B3), B3LYP and MP2 computational methods of para-substituted benzaldehyde compounds. J Comput Chem. 2021;42:1106–1117. doi:10.1002/jcc.26538
   PubMed Web of Science ®Google Scholar
• Khalid M, Ali A, Jawaria R, et al. First principles study of electronic and nonlinear optical properties of A–D–π–A and D–A–D–π–A configured compounds containing novel quinoline–carbazole derivatives. RSC Adv. 2020;10:22273–22283. doi:10.1039/D0RA02857F
   PubMed Web of Science ®Google Scholar
• Yang D, Zhang Q, Song X, et al. Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems. RSC Adv. 2019;9:23004–23011. doi:10.1039/C9RA04258J
   PubMed Web of Science ®Google Scholar
• Becke AD. Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing. J Chem Phys. 1996;104:1040–1046. doi:10.1063/1.470829
   Web of Science ®Google Scholar
• Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100. doi:10.1103/PhysRevA.38.3098
   PubMed Web of Science ®Google Scholar
• Lee C, Yang W, Parr R. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B: Condens Matter Mater Phys. 1988;37:785–789. doi:10.1103/physrevb.37.785
   Google Scholar
• Gaussian09, Frisch MJ, Trucks GW, et al. Wallingford (CT): Gaussian. Inc.; 2009. 121. p. 150–166.
   Google Scholar
• Scott AP, Radom L. Harmonic vibrational frequencies: an evaluation of hartree−fock, møller−plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem. 1996;100:16502–16513. doi:10.1021/jp960976r
   Web of Science ®Google Scholar
• McLean A, Chandler G. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18. J Chem Phys. 1980;72:5639. doi:10.1063/1.438980
   Web of Science ®Google Scholar
• Clark T, Chandrasekhar J, Spitznagel GW, et al. Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F. J Comput Chem. 1983;4:294–301. doi:10.1002/jcc.540040303
   Web of Science ®Google Scholar
• Mennucci B, Tomasi J, Cammi R, et al. Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J Phys Chem A. 2002;106:6102–6113. doi:10.1021/jp020124t
   Web of Science ®Google Scholar
• Lu T, Chen F. Multiwfn: A multifunctional wavefunction analyzer. J Comput Chem. 2012;33:580–592. doi:10.1002/jcc.22885
   PubMed Web of Science ®Google Scholar
• Reed AE, Weinstock RB, Weinhold F. Natural population analysis. J Chem Phys. 1985;83:735–746. doi:10.1063/1.449486
   Web of Science ®Google Scholar
• William H. VMD: visual molecular dynamics. J Mol Graph. 1996;14:33–38. doi:10.1016/0263-7855(96)00018-5
   PubMedGoogle Scholar
• Humphrey W, Dalke A, Schulten K. VMD: visual molecular dynamics. J Mol Graph. 1996;14:33–38. doi:10.1016/0263-7855(96)00018-5
   PubMed Web of Science ®Google Scholar
• Kelley TWC. gnuplot 5.5 an interactive plotting program. 2004–2021. Available from: http://sourceforge.net/projects/gnuplot
   Google Scholar
• Ditchfield R. Self-consistent perturbation theory of diamagnetism. Mol Phys. 1974;27:789–807. doi:10.1080/00268977400100711
   Web of Science ®Google Scholar
• Wolinski K, Hinton JF, Pulay P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 1990;112:8251–8260. doi:10.1021/ja00179a005
   Web of Science ®Google Scholar
• Garza AJ, Osman OI, Scuseria GE, et al. Nonlinear optical properties of DPO and DMPO: a theoretical and computational study. Theor Chem Acc. 2013;132:1. doi:10.1007/s00214-013-1384-2
   Web of Science ®Google Scholar
• Yanai T, Tew DP, Handy NC. A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem Phys Lett. 2004;393:51–57. doi:10.1016/j.cplett.2004.06.011
   Web of Science ®Google Scholar
• Tomasi J, Mennucci B, Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005;105:2999. doi:10.1021/cr9904009
   PubMed Web of Science ®Google Scholar
• Kazemi Z, Ghiasi R, Jamehbozorgi S. Analysis of the interaction between the C20 cage and cis-Ptcl2(NH3)2: a DFT investigation of the solvent effect, structures, properties, and topologies. J Struct Chem. 2018;59:1044–1051. doi:10.1134/S0022476618050050
   Google Scholar
• Kazemi Z, Ghiasi R, Jamehbozorgi S. The interaction of 5-fluorouracil with graphene in presence of external electric field: a theoretical investigation. Adsorption. 2020;26:905–911. doi:10.1007/s10450-019-00140-3
   Web of Science ®Google Scholar
• Shabani M, Ghiasi R, Zare K, et al. The interaction between carboplatin anticancer drug and B12N12 nano-cluster: A computational investigation. Main Group Chem. 2021;20:345–354. doi:10.3233/MGC-210051
   Web of Science ®Google Scholar
• Ghiasi R, Valizadeh A. Computational investigation of interaction of a cycloplatinated thiosemicarbazone as antitumor and antiparasitic agents with B12N12 nano-cage. Results Chem. 2023;5:100768. doi:10.1016/j.rechem.2023.100768
   Google Scholar
• Ghiasi R, Valizadeh A. Interaction of cisplatin anticancer drug with C20 bowl: DFT investigation. Main Group Chem. 2022;21:43–54. doi:10.3233/MGC-210076
   Web of Science ®Google Scholar
• Ashfaq M, Tahir MN, Kuznetsov A, et al. DFT and single crystal analysis of the pyrimethamine-based novel co-crystal salt: 2,4-diamino-5-(4-chloro-phenyl)-6-ethylpyr-imidin-1-ium:4-hydroxybenzoate:methanol:hydrate(1:1:1:1) (DEHMH). J Mol Struct. 2020;1199:127041. doi:10.1016/j.molstruc.2019.127041
   Web of Science ®Google Scholar
• Fukui K. Role of frontier orbitals in chemical reactions. Science. 1982:218;747–754.
   PubMed Web of Science ®Google Scholar
• Yang W, Parr RG, Pucci R. Electron density, Kohn–Sham frontier orbitals, and Fukui functions. J Chem Phys. 1984;81:2862–2863. doi:10.1063/1.447964
   Web of Science ®Google Scholar
• Yang W, Parr RG. Hardness, softness, and the fukui function in the electronic theory of metals and catalysis. Proc Natl Acad Sci USA. 1985;82:6723–6726.
   PubMed Web of Science ®Google Scholar
• Melin J, Aparicio F, Subramanian V, et al. Is the fukui function a right descriptor of hard−hard interactions? J Phys Chem A. 2004;108:2487–2491. doi:10.1021/jp037674r
   Web of Science ®Google Scholar
• Valizadeh A, Ghiasi R. Theoretical approach to the molecular structure, chemical reactivity, molecular orbital analysis, spectroscopic properties (IR, UV, NMR), and NBO analysis of deferiprone. J Struct Chem. 2017;58:1307–1317. doi:10.1134/S002247661707006X
   Web of Science ®Google Scholar
• Shalmani GG, Ghiasi R, Marjani A. EDA, CDA and QTAIM investigations in the (para-C5H4X) Ir(PH3)3 Iridabenzene Complexes. Russ J Phys Chem B. 2021;15:S6–S13. doi:10.1134/S1990793121090141
   Web of Science ®Google Scholar
• Parra RD, Ohlssen J. Cooperativity in intramolecular bifurcated hydrogen bonds: an Ab initio study. J Phys Chem A. 2008;112:3492–3498. doi:10.1021/jp711956u
   PubMed Web of Science ®Google Scholar
• Ziółkowski M, Grabowski SJ, Leszczynski J. Cooperativity in hydrogen-bonded interactions: Ab initio and “atoms in molecules” analyses. J Phys Chem A. 2006;110:6514. doi:10.1021/jp060537k
   PubMed Web of Science ®Google Scholar
• Ghiasi R, Sadeghi N. Evolution of the interaction between C20 cage and Cr(CO)5: a solvent effect, QTAIM and EDA investigation. J Theor Comput Chem. 2017;16:1750007. doi:10.1142/S0219633617500079
   Web of Science ®Google Scholar
• Raissi H, Jalbout A, Nasseria M, et al. The effect of substitution on the intramolecular hydrogen bonding in 3-hydroxy-propenethial. Int J Quantum Chem. 2008;108:1444–1451. doi:10.1002/qua.21603
   Web of Science ®Google Scholar
• Raissi H, Khanmohammadi A, Mollania F. A theoretical DFT study on the structural parameters and intramolecular hydrogen-bond strength in substituted (Z)-N-(thioni-trosomethylene)thiohydroxylamine systems. Bull Chem Soc Jpn 2013;86:1261–1271. doi:10.1246/bcsj.20120242
   Web of Science ®Google Scholar
• Swain CG, Lupton EC. Field and resonance components of substituent effects. J Am Chem Soc 1968;90:4328. doi:10.1021/ja01018a024
   Web of Science ®Google Scholar
• Shabani M, Ghiasi R, Zare K, et al. Quantum chemical study of interaction between titanocene dichloride anticancer drug and Al12N12 nano-cluster. Russ J Inorg Chem. 2020;65:1726–1734. doi:10.1134/S0036023620110169
   Google Scholar
• Zafar F, Mehboob MY, Hussain R, et al. Bromophenol blue doped in nano-droplet: spectroscopy, nonlinear optical properties and Staphylococcus aureus treatment. Opt Quantum Electron. 2021;53:1. doi:10.1007/s11082-020-02634-9
   Web of Science ®Google Scholar
• Franken PA, Hill AE, Peters CW, et al. Generation of optical harmonics. Phys Rev Lett 1961;7:118–119. doi:10.1103/PhysRevLett.7.118
   Web of Science ®Google Scholar
• Lin J, Chen C, Choosing a nonlinear crystal. Lasers Opt. 1987:6;59–63.
   Google Scholar
• Ullah F, Ayub K, Mahmood T. Remarkable second and third order nonlinear optical properties of organometallic C6Li6–M3O electrides. New J Chem. 2020;44:9822–9829. doi:10.1039/D0NJ01670E
   Web of Science ®Google Scholar
• Wazzan N. MP2 calculations of the effect of the π-conjugation on the electronic and nonlinear optical properties of para-nitroaniline (pNA) derivatives. Opt Mater (Amst). 2020;110:110465. doi:10.1016/j.optmat.2020.110465
   Web of Science ®Google Scholar
• Hussain A, Khan MU, Ibrahim M, et al. Structural parameters, electronic, linear and nonlinear optical exploration of thiopyrimidine derivatives: a comparison between DFT/TDDFT and experimental study. J Mol Struct. 2020;1201:127183. doi:10.1016/j.molstruc.2019.127183
   Web of Science ®Google Scholar
• Khalid M, Arshad MN, Murtaza S, et al. Enriching NLO efficacy via designing non-fullerene molecules with the modification of acceptor moieties into ICIF2F: an emerging theoretical approach. RSC Adv. 2022;12:13412–13427. doi:10.1039/D2RA01127A
   PubMed Web of Science ®Google Scholar
• Tariq S, Raza AR, Khalid M, et al. Synthesis and structural analysis of novel indole derivatives by XRD, spectroscopic and DFT studies. J Mol Struct. 2020;1203:127438. doi:10.1016/j.molstruc.2019.127438
   Web of Science ®Google Scholar
• Bijani D, Ghiasi R, Baniyaghoob S. DFT investigation of stability, electronic and optical properties of coordination of C20 corannulene to Fe(CO)4. Inorg Chem Commun. 2023;153:110793. doi:10.1016/j.inoche.2023.110793
   Web of Science ®Google Scholar
• Asadzadeh H, Ghiasi R, Yousefi M, et al. C-PCM study on the electronic and optical properties of Fe(CO)4B12N12 complexes. Main Group Chem. 2023;22:1.
   Web of Science ®Google Scholar
• Ghiasi R, Rahimi M. Solvent effect on the nonlinear optical property in Cr(CO)3L complexes (L = η6-benzene and η6-graphene): a theoretical study. Russ J Phys Chem B. 2023;17:27–35. doi:10.1134/S1990793123010207
   Web of Science ®Google Scholar