Green Solvent-Free Microwave Synthesis, Spectroscopic and Computational (DFT) Characterization, and Molecular Docking of the Bis-Schiff Base Derived from Hexamethylenediamine and Benzaldehyde
Subject Areas :
1 - Ardabil branch, izlamic azad university
Keywords: Schiff base, hexamethylenediamine, Benzaldehyde, molecular docking, Density Functional Theory (DFT), green synthesis ,
Abstract :
Schiff bases are organic compounds characterized by the imine functional group (C=N) formed by condensing primary amines and carbonyl compounds. Their versatile chemical properties and broad range of applications have led to ongoing interest in their synthesis and functionality. This paper presents a green synthesis of EE-bis-Schiff base from hexamethylenediamine and benzaldehyde using solvent-free conditions and microwave irradiation, enhancing reaction efficiency while minimizing environmental impact. Characterization of the synthesized compound was conducted via FT-IR spectroscopy and CHN analysis. Furthermore, comprehensive Density Functional Theory (DFT) studies were performed at the B3LYP/6-311g(d,p) level of theory, providing insights into the molecular structure, stability, and electronic properties of EE-bis-Schiff base. Computationally molecular structure, thermodynamic stability, infrared spectrum analysis, ultraviolet-visible absorption spectrum, nuclear magnetic resonance (NMR) spectra analysis, HOMO‒LUMO energies, quantum molecular descriptors, map of electrostatic potential, and Mulliken atomic charges analysis of this Schiff base were studied. Also, molecular docking of EE-bis-Schiff base with 1AJ6, 6LU7, and 1HSG receptors was done.
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[1] Vahideh Hadigheh Rezvan, Alireza Afsaneh, Green synthesis of a novel bis-Schiff base derived from 4-N, N-dimethylaminobenzaldehyde and hexamethylenediamine: DFT study, J. Mol. Struc., 2024, 1313, 5, 138744-138756. https://doi.org/10.1016/j.molstruc.2024.138744
[2] Jean-Baptiste, K., Guillaume, K., Adama, O., Claude, K., Jacques, D., Antoine, K., Nahosse, Z. Synthesis, Characterization, and Biological Evaluation of a New Series of Schiff Bases Derived from Hexamethylenediamine as Potential Antibacterial and Antifungal Agents, IRA-International J. Applied Sciences, 2017, 7(2), 69-74. doi: http://dx.doi.org/10.21013/jas.v7.n2.p3
[3] Aragón-Muriel, A., Reyes-Márquez, V., Cañavera-Buelvas, F., Parra-Unda, J.R., Cuenú-Cabezas, F., Polo-Cerón, D., Colorado-Peralta, R., Suárez-Moreno, G.V., Aguilar-Castillo, B.A., Morales‐Morales, D., Pincer Complexes Derived from Tridentate Schiff Bases for Their Use as Antimicrobial Metallopharmaceuticals, Inorganics, 2022, 10(9), 134. https://doi.org/10.3390/inorganics10090134
[4] Mohammed Abduljleel, A., Saleh Alshawi, J.M., Ali Hussein, K., Ismael, S.M., Synthesis, characterization, biological studies and DFT study of Schiff Bases and their complexes derived from aromatic diamine compounds with Cobalt (II), Bionatura, 2023, 8 (1) 61. http://dx.doi.org/10.21931/RB/2023.08.01.61
[5] Asha Fadllallah Wady1, Abdalla Gobara Habieballa2, Mohammed Awad Khalid3 and Yusuf Sulfab Ahmed, Synthesis, characterization of schiff bases derived from salicylaldehyde with some amino acids and its oxovanadium (IV) complexes via a new developed method, IOSR J. Applied Chem. (IOSR-JAC), 2022, 15 (6), 43-57. DOI: 10.9790/5736-1506014357
[6] Çelik, F., Kadriye Inan Bektas, H. İbrahim Güler, Ş. Direkel, Y. Ünver, New Schiff Bases with Thiophene Ring: Synthesis, Biological Activities, and Molecular Docking Study, Russian J. General Chem., 2023, 93, 409-417. https://api.semanticscholar.org/CorpusID:257838602
[7] Mukhtar, S., Hassan, A., Morsy, N., Hafez, T., Hassaneen, H., Saleh, F. Overview on Synthesis, Reactions, Applications, and Biological Activities of Schiff Bases, Egyptian J. Chem., 2021, 64(11), 6541-6554. doi: 10.21608/ejchem.2021.79736.3920
[8] Al-Mudhafar, May Mohammed Jawad, Tagreed N-A Omar, Shayma L. Abdulhadi. Bis-Schiff Bases of Isatin Derivatives Synthesis, and their Biological Activities: A Review, Al Mustansiriyah J. Pharmaceutical Sciences, 2022, 22(1), 23-48. https://doi.org/10.32947/ajps.v22i1.827
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