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

Nahed Hazim Al-Haidery; Suhad Rajab Kareem; Sabah Abbas Malik; Shaker Abdel Salem Al-Jadaan; Nuha Hussain Al-Saadawy

doi:10.22146/ijc.88463

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

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

(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 Pharmaceutical Chemistry, Branch of Pharmaceutical Chemistry, University of Kufa, Najaf 54001, Iraq
(4) Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah, Basrah 61004, Iraq
(5) 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

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