Spectroscopic, crystal structural, theoretical and biological studies of phenylacetohydrazide Schiff base derivatives and their copper complexes
Abstract
Two phenylacetohydrazide Schiff base derivatives: N’-(1-(2-hydroxyphenyl)ethylidene)-2-phenylacetohydrazide, HL1, and N’-((1-hydroxynaphthalen-2-yl)methylene)-2-phenylacetohydrazide, HL2, were synthesized. HL1 dimerizes in presence of HCl, probably via radical mechanism to give (2,2’-((1E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))diphenol (DIM). Thermal reactions of Cu(II) ions with the two Schiff base ligands resulted in formation of the binuclear complexes [(CuL1)2] and [(CuL2)2]. The stoichiometry and structures of the reported compounds were investigated by several spectroscopic and analytical techniques. The structure of the HL1 ligand and its complex [(CuL1)2] as well as the DIM derivative were analyzed by single crystal X-ray analysis. The X-ray analysis revealed the binuclear coordination of the copper complex with the formation of five- and six-membered rings with every ligand. The molecular geometries of the ligands and their copper complexes were investigated using the DFT‐B3LYP/GENECP level of theory. The optimized structures of the studied complexes are consistent with the finding of the X-ray analysis. The quantum, non-quantum global reactivity descriptors and the non-linear optical properties were calculated. Biological studies including, antimicrobial and antioxidant activities of the complexes along with fluorescence quenching studies and viscosity measurements are carried out. The molecular docking of the two ligands and [(CuL2)2] complex is also reported. The different biological studies as well as molecular docking are correlated to each other and supported the fact that the complexes can bind to DNA via intercalative mode and showed a various DNA binding potency.
Main Authors
Format
Articles
Research article
Published
2020
Series
Subjects
Publication in research information system
Publisher
Elsevier
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202002252189Use this for linking
Review status
Peer reviewed
ISSN
0022-2860
DOI
https://doi.org/10.1016/j.molstruc.2020.127860
Language
English
Published in
Journal of Molecular Structure
Citation
- El-Medani, S. M., Makhlouf, A. A., Moustafa, H., Afifi, M. A., Haukka, M., & Ramadan, R. M. (2020). Spectroscopic, crystal structural, theoretical and biological studies of phenylacetohydrazide Schiff base derivatives and their copper complexes. Journal of Molecular Structure, 1208, Article 127860. https://doi.org/10.1016/j.molstruc.2020.127860
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