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Structural studies and biological evaluation of Co (II), Ni (II) and Cu (II) complexes of carbohydrazone derived from ethyl acetoacetate in addition to crystallographic description of La (III) or Sm (III) catalytic activity abnormal product
Author(s) -
Fetoh Ahmed,
Salah Zeinab,
Abu ElReash Gaber M.
Publication year - 2019
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4727
Subject(s) - chemistry , ethyl acetoacetate , ligand (biochemistry) , carbohydrazide , denticity , deprotonation , enol , moiety , medicinal chemistry , chelation , acetylacetone , stereochemistry , crystallography , catalysis , inorganic chemistry , crystal structure , organic chemistry , ion , biochemistry , receptor
New carbohydrazone ligand derived from the condensation of carbohydrazide and ethyl acetoacetate, diethyl 3,3′‐(carbonylbis (hydrazin‐2‐yl‐1‐ylidene))(3 E ,3′ E )‐dibutyrate (H 4 EBC), and its divalent Co, Ni and Cu chelates have been isolated and characterized utilizing convenient methods. 1 H‐NMR spectrum of H 4 EBC revealed the abundance of the enol isomer in solution, which was the opposite to what was shown by the solid IR. This was supported by comparing the theoretical IR of both keto and enol forms. In [Ni(H 4 EBC)Cl 2 (H 2 O)]·2H 2 O, H 4 EBC acts as a neutral NON tridentate ligand via the (C=O) carbonyl oxygen atom besides the two (C=N) azomethine nitrogen atoms, while in [Co(H 4 EBC)Cl 2 (2H 2 O)]·2H 2 O, H 4 EBC behaves as a neutral NN bidentate ligand through the two azomethine groups. Magnetic measurements inherent to their electronic spectra show that both Ni (II) and Co (II) chelates have octahedron coordination frameworks. On the other hand, the ligand behaves as a binegative tetradentate in [Cu 2 (H 4 EBC)Cl 2 ]·H 2 O via the deprotonated (C=O) carbonyl groups of the ethyl acetoacetate framework and the two (C=N) azomethine groups. In the latter complex, the carbonyl group of the carbohydrazide moiety is converted to hydroxyl group. Cu (II) complex has a tetrahedral geometry according to ESR and electronic spectral data. The reaction of H 4 EBC with SmCl 3 ·6H 2 O or LnCl 3 ·7H 2 O gave single crystals of abnormal product (C 16 H 16 N 4 O 4 ). The packing diagram of this crystal has a chain structure. The photoluminescence spectra of [Cu 2 (H 4 EBC)Cl 2 ]·H 2 O , [Co(H 4 EBC)Cl 2 (H 2 O) 2 ]·2H 2 O and [Ni(H 4 EBC)Cl 2 (H 2 O)]·2H 2 O display emission broad‐bands at 342, 321 and 337 nm, respectively. The microbial behavior of the synthesized moieties was investigated against various bacterial and fungal strains. [Cu 2 (H 4 EBC)Cl 2 ]·H 2 O complex shows the same activity as ampicillin towards Escherichia coli and Staphylococcus aureus with inhibition zones of 26 and 22 mm, respectively. Antioxidant activity is determined using bleomycin‐dependent DNA damage assay besides erythrocyte hemolysis. Finally, in vitro cytotoxic activities against two different cell lines have been examined.