Synthesis, spectroscopic characterization, antimicrobial activity, molecular docking and DFT studies of proton transfer (H-bonded) complex of 8-aminoquinoline (donor) with chloranilic acid (acceptor)

References

• Adam, A. M. A., & Refat, M. S. (2015). Nanostructured products of the drug theophylline caused by charge transfer interactions and a binary solvent system: Morphologyand nanometry. Journal of Molecular Liquids, 209, 33–41. https://doi.org/10.1016/j.molliq.2015.05.021
   Web of Science ®Google Scholar
• Adam, A. M. A., & Refat, M. S. (2016). Solution and solid-state investigations of charge transfer complexes caused by the interaction of bathophenanthroline with different organic acceptors in a (methanol + dichloromethane) binary solvent system. Journal of Molecular Liquids, 219, 377–389. https://doi.org/10.1016/j.molliq.2016.03.045
   Web of Science ®Google Scholar
• Akram, M., Lal, H., Shakya, S., & Kabir-Ud-Din. (2020). Multispectroscopic and computational analysis insight into the interaction of cationic diester-bonded gemini surfactants with serine protease α-chymotrypsin. ACS Omega, 5, 3624–3637.
   PubMed Web of Science ®Google Scholar
• Al-Ahmary, K. M., Alenezi, M. S., & Habeeb, M. M. (2016). Synthesis, spectroscopic and DFT theoretical studies on the hydrogen bonded charge transfer complex of 4-aminoquinoline with chloranilic acid. Journal of Molecular Liquids, 220, 166–182. https://doi.org/10.1016/j.molliq.2016.04.074
   Web of Science ®Google Scholar
• Al-Ahmary, K. M., Habeeb, M. M., & Al-Obidan, A. H. (2018). Charge transfer complex between 2,3-diaminopyridine with chloranilic acid. Synthesis, characterization and DFT, TD-DFT computational studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 196, 247–255. https://doi.org/10.1016/j.saa.2018.02.025
   PubMed Web of Science ®Google Scholar
• Aloisi, G. G., & Pignataro, S. (1973). Molecular complexes of substituted thiophens with σ and π acceptors. Charge transfer spectra and ionization potentials of the donors. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 69(0), 534–539. https://doi.org/10.1039/f19736900534
   Google Scholar
• Atkins, P. W. (1990). Physical chemistry (4th ed., Vol. 94, p. 1171). Oxford University Press.
   Google Scholar
• Bellamy, L. J., & Bellamy, L. J. (1975). Introduction. In The infra-red spectra of complex molecules (pp. 1–9). Springer. https://doi.org/10.1007/978-94-011-6017-9_1
   Google Scholar
• Benesi, H. A., & Hildebrand, J. H. (1949). A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8), 2703–2707. https://doi.org/10.1021/ja01176a030
   Web of Science ®Google Scholar
• Briegleb, G., & Czekalla, J. (1960). ElektronenüberführungdurchLichtabsorption und -emission in Elektronen-Donator-Acceptor-Komplexen. AngewandteChemie, 72, 401–413.
   Google Scholar
• Büyükmurat, Y., Akalin, E., Özel, A. E., & Akyüz, S. (1999). Calculation and analysis of IR spectrum of 2-aminopyridine. Journal of Molecular Structure, 482, 579–584.
   Web of Science ®Google Scholar
• Collins, A. H. (Ed.). (1976). Microbiology method (2nd ed.). London.
   Google Scholar
• Cruickshank, R., Duguid, J. P., Marmion, B. P., & Awain, R. H. A. (1995). Medicinal microbiology (12th ed., Vol. 196). Churchill Livingstone.
   Google Scholar
• Dabestani, R., Reszka, K. J., & Sigman, M. E. (1998). Surface catalyzed electron transfer from polycyclic aromatic hydrocarbons (PAH) to methyl viologendication: Evidence for ground-state charge transfer complex formation on silica gel. Journal of Photochemistry and Photobiology A: Chemistry, 117(3), 223–233. https://doi.org/10.1016/S1010-6030(98)00327-X
   Web of Science ®Google Scholar
• Di Bella, S., Fragala, I. L., Ratner, M. A., & Marks, T. J. (1993). Electron donor-acceptor complexes as potential high-efficiency second-order nonlinear optical materials. A computational investigation. Journal of the American Chemical Society, 115(2), 682–686. https://doi.org/10.1021/ja00055a043
   Web of Science ®Google Scholar
• Dozal, A., Keyzer, H., Kim, H. K., & Wang, W. W. (2000). Charge transfer complexes of K vitamins with several classes of antimicrobials. International Journal of Antimicrobial Agents, 14(3), 261–265. https://doi.org/10.1016/s0924-8579(99)00163-6
   PubMed Web of Science ®Google Scholar
• Elsayed, M. A. H., & Agarwal, S. P. (1982). Spectrophotometric determination of atropine, pilocarpine and strychnine with chloranilic acid. Talanta, 29(6), 535–537. https://doi.org/10.1016/0039-9140(82)80212-9
   PubMed Web of Science ®Google Scholar
• Eychmüller, A., & Rogach, A. L. (2000). Chemistry and photophysics of thiol-stabilized II-VI semiconductor nanocrystals. Pure and Applied Chemistry, 72(1–2), 179–188. https://doi.org/10.1351/pac200072010179
   Web of Science ®Google Scholar
• Foster, R. (1969). Charge transfer complexes. Academic Press.
   Google Scholar
• Frisch, M. J., & Trucks, G. W. (2004). Gaussian 03. Gaussian, Inc.
   Google Scholar
• Grossel, M. C., & Weston, S. C. (1996). A truly isolated TCNQ•-dimer? Chemistry of Materials, 8(5), 977–980. https://doi.org/10.1021/cm9505052
   Web of Science ®Google Scholar
• Gutmann, F., Johnson, C., Keyzer, H., & Molnar, J. (1992). Charge transfer complexes in biochemistry systems. Marcel Dekker Inc.
   Google Scholar
• Hamed, M. M. A., Abdel-Hamid, M. I., & Mahmoud, M. R. (1998). Molecular complexes of some n-aryldithiocarbamates with p-electron acceptors. Monatshefte fuÈr Chemie, 129(2), 121–127.
   Web of Science ®Google Scholar
• Hasani, M., & Rezaei, A. (2006). Spectrophotometric study of the charge-transfer complexes of iodine with antipyrine in organic solvents. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 65(5), 1093–1097. https://doi.org/10.1016/j.saa.2006.02.009
   PubMed Web of Science ®Google Scholar
• Hu, Y. J., Liu, Y., Zhang, L. X., Zhao, R. M., & Qu, S. S. (2005). Studies of interaction between colchicine and bovine serum albumin by fluorescence quenching method. Journal of Molecular Structure, 750(1–3), 174–178. https://doi.org/10.1016/j.molstruc.2005.04.032
   Web of Science ®Google Scholar
• Islam, M. R., Shakya, S., Selim, A., Alam, M. S., & Ali, M. (2019). Solvatochromic absorbance and fluorescence probe behavior within ionic liquid+ γ-butyrolactone mixture. Journal of Chemical & Engineering Data, 64(9), 4169–4180. https://doi.org/10.1021/acs.jced.9b00576
   Web of Science ®Google Scholar
• Jeffrey, G. A. (1997). An introduction to hydrogen bonding. Oxford University Press.
   Google Scholar
• Kasha, M. (1991). Energy transfer, charge transfer, and proton transfer in molecular composite systems. Basic Life Sciences, 58, 231–255. https://doi.org/10.1007/978-1-4684-7627-9_8
   PubMedGoogle Scholar
• Khan, I. M., & Ahmad, A. (2010). Synthesis, spectral investigations, antimicrobial activity and DNA-binding studies of novel charge transfer complex of 1,10-phenanthroline as an electron donor with π-acceptor p-Nitrophenol. Journal of Molecular Structure, 977(1–3), 189–196. https://doi.org/10.1016/j.molstruc.2010.05.031
   Web of Science ®Google Scholar
• Khan, I. M., Ahmad, A., & Ullah, M. F. (2011). Synthesis, crystal structure, antimicrobial activity and DNA-binding of hydrogen-bonded proton-transfer complex of 2,6-diaminopyridine with picric acid. Journal of Photochemistry and Photobiology B: Biology, 103(1), 42–49. https://doi.org/10.1016/j.jphotobiol.2011.01.010
   PubMed Web of Science ®Google Scholar
• Khan, I. M., Ahmad, A., & Ullah, M. F. (2013). Synthesis, spectroscopic investigations, antimicrobial and DNA binding studies of a new charge transfer complex of o-phenylenediamine with 3,5-dinitrosalicylic acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 102, 82–87. https://doi.org/10.1016/j.saa.2012.10.027
   PubMed Web of Science ®Google Scholar
• Khan, I. M., Alam, K., Afshan, M., Shakya, S., & Islam, M. (2020a). Thermodynamic and structural studies of newly prepared CT complex betweenpyrazole as a donor and salicylic acid as acceptor at various temperatures in ethanol. Journal of Molecular Structure, 1206, 127758. https://doi.org/10.1016/j.molstruc.2020.127758
   Web of Science ®Google Scholar
• Khan, I. M., Islam, M., Shakya, S., Alam, K., Alam, N., & Shahid, M. (2020b). Synthesis, characterization, antimicrobial and DNA binding properties of an organic charge transfer complex obtained from pyrazole and chloranilic acid. Bioorganic Chemistry, 99, 103779. https://doi.org/10.1016/j.bioorg.2020.103779
   PubMed Web of Science ®Google Scholar
• Khan, I. M., & Shakya, S. (2019). Exploring colorimetric real-time sensing behavior of a newly designed CT complex toward nitrobenzene and Co2+: Spectrophotometric, DFT/TD-DFT, and mechanistic insights. ACS Omega, 4(6), 9983–9995. https://doi.org/10.1021/acsomega.9b01314
   PubMed Web of Science ®Google Scholar
• Khan, I. M., Shakya, S., Akhtar, R., Alam, K., Islam, M., & Alam, N. (2020c). Exploring interaction dynamics of designed organic cocrystal charge transfer complex of 2-hydroxypyridine and oxalic acid with human serum albumin: Single crystal, spectrophotometric, theoretical and antimicrobial studies. Bioorganic Chemistry, 100, 103872. https://doi.org/10.1016/j.bioorg.2020.103872
   PubMed Web of Science ®Google Scholar
• Khan, I. M., Shakya, S., Islam, M., Khan, S., & Najnin, H. (2020d). Synthesis and spectrophotometric studies of CT complex between 1,2-dimethylimidazole and picric acid in different polar solvents: Exploring antimicrobial activities and molecular (DNA) docking. Physics and Chemistry of Liquid, 1–17. https://doi.org/10.1080/00319104.2020.1810250
   Google Scholar
• Khan, I. M., Shakya, S., & Singh, N. (2018). Preparation, single-crystal investigation and spectrophotometric studies of proton transfer complex of 2,6-diaminopyridine with oxalic acid in various polar solvents. Journal of Molecular Liquids, 250, 150–161. https://doi.org/10.1016/j.molliq.2017.11.150
   Web of Science ®Google Scholar
• Khan, M. D., Shakya, S., Vu, H. H. T., Habte, L., & Ahn, J. W. (2021). Low concentrated phosphorus sorption in aqueous medium on aragonite synthesized by carbonation of seashells: Optimization, kinetics, and mechanism study. Journal of Environmental Management, 280, 111652. https://doi.org/10.1016/j.jenvman.2020.111652
   PubMed Web of Science ®Google Scholar
• Martin, A. N., Swarbrick, J., & Cammarata, A. (1969). Physical pharmacy (3rd, Lee, 344p, Feb I. Ger, Eds.). Lee and Febiger.
   Google Scholar
• Miyan, L., Zulkarnain, & Ahmad, A. (2018). Spectroscopic and spectrophotometric studies on hydrogen bonded charge transfer complex of 2-amino-4-methylthiazole with chloranilic acid at different temperatures. Journal of Molecular Liquids, 262, 514–526.
   Web of Science ®Google Scholar
• Mulliken, R. S. (1950). Structures of complexes formed by halogen molecules with aromatic and with oxygenated solvents. Journal of the American Chemical Society, 72(1), 600–608. https://doi.org/10.1021/ja01157a151
   Web of Science ®Google Scholar
• Mulliken, R. S., & Pearson, W. B. (1969). Molecular complexes. Wiley Publishers.
   Google Scholar
• Mulliken, R. S., & Pearson, W. B. (2006). Molecular complexes. Wiley Publishers (1969).
   Google Scholar
• Nour, E. M. (2000). Resonance Raman study of the polyiodide complex formed in the reaction of iodine with the polysulphur cyclic base 1,4,7,10,13,16-hexathiacyclooctadecane. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 56(1), 167–170. https://doi.org/10.1016/S1386-1425(99)00130-4
   Web of Science ®Google Scholar
• Papadakis, R. (2019). Mono-and di-quaternized 4, 4′-bipyridine derivatives as key building blocks for medium-and environment-responsive compounds and materials. Molecules, 25(1), 1. https://doi.org/10.3390/molecules25010001
   PubMed Web of Science ®Google Scholar
• Papadakis, R., Deligkiozi, I., Giorgi, M., Faure, B., & Tsolomitis, A. (2016). Supramolecular complexes involving non-symmetric viologen cations and hexacyanoferrate (II) anions. A spectroscopic, crystallographic and computational study. RSC Advances, 6(1), 575–585. https://doi.org/10.1039/C5RA16732A
   Web of Science ®Google Scholar
• Pauling, L. (1960). The nature of the chemical bond—An introduction to modern structural chemistry (3rd ed., Vol. 260, pp. 10–13). Cornell University Press.
   Google Scholar
• Refat, M. S., El-Deen, I. M., Ibrahim, H. K., & El-Ghool, S. (2006). Synthesis and spectroscopic studies of some transition metal complexes of a novel Schiff base ligands derived from 5-phenylazo-salicyladehyde and o-amino benzoic acid. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 65(5), 1208–1220. https://doi.org/10.1016/j.saa.2006.01.049
   PubMed Web of Science ®Google Scholar
• Ritchie, D. W., & Venkatraman, V. (2010). Ultra-fast FFT protein docking on graphics processors. Bioinformatics (Oxford, England), 26(19), 2398–2405. https://doi.org/10.1093/bioinformatics/btq444
   PubMed Web of Science ®Google Scholar
• Rodina, L. L., Ryzhakov, A. V., & Alekseeva, O. O. (1995). The molecular complex of 4-(N-pyridinium)pyridine-N-oxide chloride with tetracyanoethylene in the synthesis of substituted pyridine N-oxides. Chemistry of Heterocyclic Compounds, 31(2), 157–159. https://doi.org/10.1007/BF01169672
   Google Scholar
• Saito, G., & Matsunaga, Y. (1974). Charge-transfer and proton-transfer in the formation of molecular complexes. VIII. Benzidine–2,4-dinitrophenol complexes. Bulletin of the Chemical Society of Japan, 47(4), 1020–1021. https://doi.org/10.1246/bcsj.47.1020
   Web of Science ®Google Scholar
• Sakurai, H., Izuoka, A., & Sugawara, T. (1997). Preparation and property of ionic CT complex of dimethylaminonitronylnitroxide with DDQ. Molecular Crystals and Liquid Crystals Science and Technology Section A, 306(1), 415–421. https://doi.org/10.1080/10587259708044596
   Web of Science ®Google Scholar
• Shakya, S., & Khan, I. M. (2021). Charge transfer complexes: Emerging and promising colorimetric real-time chemosensors for hazardous materials. Journal of Hazardous Materials, 403, 123537. https://doi.org/10.1016/j.jhazmat.2020.123537
   PubMed Web of Science ®Google Scholar
• Shakya, S., Khan, I. M., & Ahmad, M. (2020). Charge transfer complex based real-time colorimetric chemosensor for rapid recognition of dinitrobenzene and discriminative detection of Fe2+ ions in aqueous media and human hemoglobin. Journal of Photochemistry and Photobiology A: Chemistry, 392, 112402. https://doi.org/10.1016/j.jphotochem.2020.112402
   Web of Science ®Google Scholar
• Shakya, B., Shakya, S., & Hasan Siddique, Y. (2019). Effect of geraniol against arecoline induced toxicity in the third instar larvae of transgenic Drosophila melanogaster (hsp70-lacZ) Bg9. Toxicology Mechanisms and Methods, 29(3), 187–202. https://doi.org/10.1080/15376516.2018.1534299
   PubMed Web of Science ®Google Scholar
• Shukla, M., Srivastava, N., & Saha, S. (2012). Investigation of ground state charge transfer complex between paracetamol and p-chloranil through DFT and UV-visible studies. Journal of Molecular Structure, 1021, 153–157. https://doi.org/10.1016/j.molstruc.2012.04.075
   Web of Science ®Google Scholar
• Singh, N., Khan, I. M., Ahmad, A., & Javed, S. (2016). Synthesis, spectrophotometric and thermodynamic studies of charge transfer complex of 5,6-dimethylbenzimidazole with chloranilic acid at various temperatures in acetonitrile and methanol solvents. Journal of Molecular Liquids, 221, 1111–1120. https://doi.org/10.1016/j.molliq.2016.06.081
   Web of Science ®Google Scholar
• Sondhi, S. M., Johar, M., Rajvanshi, S., Dastidar, S. G., Shukla, R., Raghubir, R., & Lown, J. W. (2001). Anticancer, anti-inflammatory and analgesic activity evaluation of heterocyclic compounds synthesized by the reaction of 4-isothiocyanato-4-methylpentan-2-one with substituted o-phenylenediamines, o-diaminopyridine and (Un)substituted o-diaminopyrimidines. Australian Journal of Chemistry, 54(1), 69–74. https://doi.org/10.1071/CH00141
   Web of Science ®Google Scholar
• Takahashi, K., Horino, K., Komura, T., & Murata, K. (1993). Photovoltaic properties of porphyrin thin films mixed with o-chloranil. Bulletin of the Chemical Society of Japan, 66(3), 733–738. https://doi.org/10.1246/bcsj.66.733
   Web of Science ®Google Scholar
• Tan, L.-F., Chen, X.-J., Shen, J.-L., & Liang, X.-L. (2009). Synthesis, DNA-binding and photocleavage studies of Ru(II) complexes of phenyl-(4,5,9,14-tetraaza-benzo[b]triphenylen-1,1-yl)-methanone. Journal of Chemical Sciences, 121(4), 397–405. https://doi.org/10.1007/s12039-009-0046-3
   Web of Science ®Google Scholar
• Zhang, J., Jin, J., Xu, H., Zhang, Q., & Huang, W. (2018). Recent progress on organic donor-acceptor complexes as active elements in organic field-effect transistors. Journal of Materials Chemistry C, 6(14), 3485–3498. https://doi.org/10.1039/C7TC04389A
   Web of Science ®Google Scholar
• Zhurko, G. A., & Zhurko, D. A. (2016). Chemcraft - graphical program for visualization of quantum chemistry computations. Academic version 1.5.
   Google Scholar
• Zulkarnain, Khan, I. M., Ahmad, A., Miyan, L., Ahmad, M., & Azizc, N. (2017). Synthesis of charge transfer complex of chloranilic acid as acceptor with p-nitroaniline as donor: Crystallographic, UV–visible spectrophotometric and antimicrobial studies. Journal of Molecular Structure, 1141, 687–697.
   Web of Science ®Google Scholar