New Charge-Transfer Complexes of Organochalcogenide Compound Based on Aryl Acetamide Group with Quinones: Synthesis, Characterization, Antioxidant, and Computational Study

https://doi.org/10.22146/ijc.88463

Attared Fadhel Hassan(1), Nahed Hazim Al-Haidery(2), Suhad Rajab Kareem(3), Sabah Abbas Malik(4), Shaker Abdel Salem Al-Jadaan(5), Nuha Hussain Al-Saadawy(6*)

(1) Department of Chemistry, College of Science, University of Basrah, Basrah 61004, Iraq
(2) Department of Chemistry, College of Science, University of Basrah, Basrah 61004, Iraq
(3) Department of Chemistry, College of Science, University of Basrah, Basrah 61004, Iraq
(4) Department of Pharmaceutical Chemistry, Branch of Pharmaceutical Chemistry, University of Kufa, Najaf 54001, Iraq
(5) Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah 61004, Iraq
(6) Department of Chemistry, College of Science, University of Thi-Qar, Muthanna 64001, Iraq
(*) Corresponding Author

Abstract


This study aims to prepare charge transfer complexes derived from organochalcogenide of arylamide derivatives with different quinones. A new charge-transfer complexes have been developed through a direct reaction between (PhNHCOCH2)2Se, (o-CH3PhNHCOCH2)2Se, and (PhCH2NHCOCH2)2E, where E = S, Se, and Te are electron donors and different quinones are electron acceptors. The quinones used in the reaction were 2,3-dichloro-5,6-dicyanobenzoquinones (DDQ), 7,7’,8,8’-tetracyanoquinodimethane, and tetracyanoethane. The electron donors and electron acceptor mol were 1:1, and the reaction was conducted in acetonitrile. Infrared, 1H and 13C-NMR spectroscopic data characterized all complexes. The complexes’ antioxidant activity was evaluated through α,α-diphenyl-β-picrylhydrazyl at 10–0.312 mg/mL. The results showed that all complexes exhibited promising antioxidant activities. Among them, (PhCH2NHCOCH2)2S·DDQ compound had the least IC50 value of 6.725 mg/mL, indicating a potent scavenging property compared to other compounds. The molecular structures of charge-transfer complexes were investigated using hybrid density functional theory (B3LYP) and basis set 3-21G. We obtained geometrical structures' highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) surfaces and energy gaps through geometric optimization. We also investigated the molecular shapes and contours of the prepared compounds through geometrical optimization and compared the HOMO energy of the CT compounds to investigate donor and acceptor properties.

Keywords


density functional theory; radical scavenging activity; organochalcogenide compound; quinone charge-transfer complexes; highest occupied molecular orbital



References

[1] AlQaradawi, S.Y., Mostafa, A., and Bengali, A.A., 2016, Charge-transfer complexes formed in the reaction of 2-amino-4-ethylpyridine with π-electron acceptors, J. Mol. Struct., 1106, 10–18.

[2] Wu, L., Wu, F., Sun, Q., Shi, J., Xie, A., Zhu, X., and Dong, W., 2021, A TTF–TCNQ complex: An organic charge-transfer system with extraordinary electromagnetic response behavior, J. Mater. Chem. C, 9 (9), 3319–3323.

[3] Darwish, I.A., Khalil, N.Y., Asaif, N.A., Herqash, R.N., Sayed, A.Y., and Abdel-Rahman, H.M., 2021, Charge-transfer complex of Linifanib with 2,3-dichloro-3,5-dicyano-1,4-benzoquinone: Synthesis, spectroscopic characterization, computational molecular modelling and application in the development of novel 96-microwell spectrophotometric assay, Drug Des., Dev. Ther., 15, 1167–1180.

[4] Adam, A.M.A., and Refat, M.S., 2021, A comparison of charge-transfer complexes of iodine with some antibiotics formed through two different approaches (liquid-liquid vs solid-solid), J. Mol. Liq., 329, 115560.

[5] Khan, I.M., Alam, K., and Alam, M.J., 2020, Exploring charge transfer dynamics and Photocatalytic behavior of designed donor-acceptor complex: Characterization, spectrophotometric and theoretical studies (DFT/TD-DFT), J. Mol. Liq., 310, 113213.

[6] Kato, Y., Matsumoto, H., and Mori, T., 2021, Absence of HOMO/LUMO transition in charge-transfer complexes thienoacenes, J. Phys. Chem., A, 125 (1), 146–153.

[7] Mohammed, H.M., and Al-Saadawy, N.H., 2022, Synthesis, characterization, and theoretical study of novel charge-transfer complexes derived from 3,4-selenadiazobebzophenone, Indones. J. Chem., 22 (6), 1663–1672.

[8] Al-Rubaie, A.Z., and Al-Masoudi, E.A., 1990, Charge-transfer complexes of 5,6-dimethyl,1,3-dihydro-2-telluraindene, with quinones, Polyhedron, 9 (6), 847–849.

[9] Yousef, T.A., Ezzeldin, E., Abdel-Aziz, H.A., Al-Agamy, M.H., and Mostafa, G.A.E., 2020, Charge transfer complex of neostigmine with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone: Synthesis, spectroscopic characterization, antimicrobial activity, and theoretical study, Drug Des., Dev. Ther., 14, 4115–4129.

[10] Shehab, O.R., AlRabiah, H., Abdel-Aziz, H.A., and Mostafa, G.A.E., 2018, Charge-transfer complexes of cefpodoxime proxetil with chloranilic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone: Experimental and theoretical studies, J. Mol. Liq., 257, 42–51.

[11] Khan, I.M., and Ahmad, A., 2010, Synthesis, spectral and thermal studies of newly Hydrogen bonded charge transfer complex of o-phenylenediamine with π acceptor picric acid, Spectrochim. Acta, Part A, 77 (2), 437–441.

[12] Lee, S., Hong, J., Jung, S.K., Ku, K., Kwon, G., Seong, W.M., Kim, H., Yoon, G., Kang, I., Hong, K., Jang, H.W., and Kang, K., 2019, Charge-transfer complexes for high-power organic rechargeable batteries, Energy Storage Mater., 20, 462–469.

[13] Divyasree, M.C., Vasudevan, K., Abdul Basith, K.K., Jayakrishnan, P., and Ramesan, M.T., 2018, Third-order nano linear optical properties phenothiazine-iodine charge transfer complexes in different proportions, Opt. Laser Technol., 105, 94–101.

[14] Gaballa, A.S., and Amin, A.S., 2015, Preparation, spectroscopic and antibacterial studies on charge-transfer complexes of 2-hydroxypyridine with picric acid and 7,7′,8,8′-tetracyano-p-quinodimethane, Spectrochim. Acta, Part A, 145, 302–312.

[15] Alam, K., and Khan, I.M., 2018, Crystallographic, dynamic and Hirshfeld surface studies of charge transfer complex of imidazole as a donor with 3,5-dinitrobenzoic acid as an acceptor: Determination of various physical parameters, Org. Electron., 63, 7–22.

[16] Khan, I.M., Ahmad, A., and Oves, M., 2010, Synthesis, characterization, spectrophotometric, structural and antimicrobial studies of new charge transfer complexes of p-pheylenediamine with π acceptor picric acid, Spectrochim. Acta, Part A, 77 (5), 1059–1064.

[17] Basha, M.T., Alganmi, R.M., Soliman, S.M., Abdel-Rahman, L.H., Shehata, M.R., and Aharby, W.J., 2022, Synthesis, spectroscopic characterization, biological activity, DNA-binding investigation combined with DFT studies of new proton-transfer complexes of 2,4-diaminopyrimidine with 2,6-dichloro-4-nitrophenol and 3,5-dinitrosalcylic acid, J. Mol. Liq., 350, 118508.

[18] Cordeiro, P.S., Chipoline, I.C., Ribeiro, R.C.B., Pinho, D.R., Ferreira, V.F., da Silva, F.C., Forezi, L.S.M., and Nascimento, V., 2022, Seleno-and telluro functionalization of quinones: Molecules with relevant biological application, J. Braz. Chem. Soc., 33 (2), 111–127.

[19] Fu, X., Li, S., Jing, F., Wang, X., Li, B., Zhao, J., Liu, Y., and Chen, B., 2016, Synthesis and biological evaluation of novel 1,2,4-thiadiazole derivatives incorporating benzisoselenazolone scaffold as potential antitumor agents, Med. Chem., 12 (7), 631–639.

[20] Shabaan, S., Ba, L.A., Abbas, M., Burkholz, T., Denkert, A., Gohr, A., Wessjohann, L.A., Sasse, F., Weber, W., and Jacob C., 2009, Multicomponent reactions for synthesis of multifunctional agents with activity against cancer, Chem. Commun., 4702–4704.

[21] Arora, E., 2023, Synthetic methodologies and applications of chalcogen (S, Se, Te) ionic liquids: a review, Phosphorus Sulfur Silicon Relat. Elem., In Press, Corrected Proof.

[22] da Cruz, E.H.G., Silvers, M.A., Jardim, G.A.M., Resende, J.M., Cavalcanti, B.C., Bomfim, I.S., Pessoa, C., de Simone, C.A., Botteselle, G.V., Braga, A.L., Nair, D.K., Namboothiri, I.N.N., Boothman, D.A., and da Silva Júnior, E.N., 2016, Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights, Eur. J. Med. Chem., 122, 1–16.

[23] Cao, L.M., Hu, C.G., Li, H.H., Huang, H.B., Ding, L.W., Zhang, J., and Chen, X.M., 2022, Molecule-enhanced electrocatalysis of sustainable oxygen evolution using organoselenium functionalized metal–organic nanosheets, J. Am. Chem. Soc., 145 (2), 1144–1154.

[24] Taha, D.K., Israa, H.H., and Rashid, H.J., 2021, Theoretical properties of Ni2Ti alloys studied: By Gaussian 09 program, J. Phys.: Conf. Ser., 1818 (1), 012054.

[25] Hassan, A.F., Abdulwahid, A.T., Al-Luaibi, M.Y., and Aljadaan, S.N., 2020, Synthesis, characterization and thermal study of some new organochalcogenide compounds containing arylamide group, Egypt. J. Chem., 64 (9), 5009–5015.

[26] Ahmed, W.M., Al-Saadawy, N.H., and Abowd, M.I., 2021, Synthesis and characterization of a new organoselenium and tellurium compounds depending on 9-chloro-10-dihydroanthracene, Ann. Rom. Soc. Cell Biol., 25 (4), 11035–11043.

[27] Shakibaie, M., Adeli-Sardou, M., Mohammadi-Khorsand, T., Zeydabadi-Nejad, M., Amirafzali, E., Amirpour-Rostami, S., Ameri, A., and Forootanfar, H., 2017, Antimicrobial and antioxidant activity of the biologically synthesized tellurium nanorods; A preliminary in vitro study, Iran. J. Biotechnol., 15 (4), 268–276.

[28] Forootanfar, H., Adeli-Sardou, M., Nikhoo, M., Mehrabani, M., Amir-Heidari, B., Shahverdi, A.R., and Shakibaie, M., 2014, Antioxidant and cytotoxic effect of biologically synthesized selenium nanoparticles in comparison to selenium dioxide, J. Trace Elem. Med. Biol., 28 (1), 75–79.

[29] Kitzmann, W.R., and Heinze, K., 2023, Charge‐transfer and spin‐flip states: Thriving as complements, Angew. Chem. Int. Ed., 62 (15), e202213207.

[30] Juliá, F., 2022, Ligand-to-metal charge transfer (LMCTt) photochemistry at 3d-metal complexes: An emerging tool for sustainable organic synthesis, ChemCatChem, 14 (19), e202200916.

[31] Khalib, A.A.K., Al-Hazam, H.A.J., and Hassan, A.F., 2022, Inhibition of carbon steel corrosion by some new organic 2-hydroselenoacetamide derivatives in HCl medium, Indones. J. Chem., 22 (5), 1269–1281.

[32] Hassan, A.F., Radhy, H.A., and Essa, A.H., 2009, Synthesis of charge-transfer complexes for 5,6-dimethyl-2,1,3-benzoselenadiazole, J. Sci. Res., 1 (3), 569–575.

[33] Mostafa, G.A.E., Yousef, T.A., Gaballah, S.T., Homoda, A.M., Al-Salahi, R., Aljohar, H.I., and AlRabiah, H., 2022, Quinine charge transfer complexes with 2,3-dichloro-5,6-dicyano-benzoquinodimethane: Spectroscopic characterization and theoretical study, Appl. Sci., 12, 987.

[34] AdilAjeel, A., and Al-Saadawy, N.H., 2021, Preparation and identification of new organoselenium compounds based on N-phenyl-2-selenocyanatoacetamide, Nat. Volatiles Essent. Oils, 8, 8090–8111.

[35] Chand, S., Tyagi, M., Tyagi, P., Chandra, S., and Sharma, D., 2019, Synthesis, characterization, DFT of novel, symmetrical, N/O-donor tetradentate Schiff’s base, its Co(II), Ni(II), Cu(II), Zn(II) complexes and their in-vitro human pathogenic antibacterial activity, Egypt. J. Chem., 62 (2), 291–310.

[36] Zhao, J., Song, P., Feng, L., Wang, X., and Tang, Z., 2023, Theoretical insights into atomic-electronegativity-regulated ESIPT behavior for B-bph-fla-OH fluorophore, J. Mol. Liq., 380, 121763.

[37] Yang, D., Yang, W., Tian, Y., and Lv, J., 2023, Unveiling the effects of atomic electronegativity on ESIPT behaviors for FQ-OH system: A theoretical study, Spectrochim. Acta, Part A, 286, 122007.

[38] Zhao, J., Jin, B., and Tang, Z., 2023, Theoretical revealing regulated ESIPT behaviors by atomic electronegativity for quercetin fluorophore, Chem. Phys. Lett., 810, 140194.

[39] Yin, F., and Fang, H., 2022, Unveiling the effects of atomic electronegativity on the ESIPT mechanism and luminescence property of new coumarin benzothiazole fluorophore: A TD-DFT exploration, Spectrochim. Acta, Part A, 275, 121118.



DOI: https://doi.org/10.22146/ijc.88463

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