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Synthesis, spectral, DFT calculations and biological studies of solvatochromic copper(II)‐ONS hydrazone derived from 2‐aminochromone‐3‐carboxaldehyde
Author(s) -
Adly Omima M.I.,
Taha Ali,
Ibrahim Magdy A.,
Fahmy Shery A.
Publication year - 2020
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.5763
Subject(s) - chemistry , solvatochromism , excited state , ground state , hydrazone , ligand (biochemistry) , crystallography , photochemistry , computational chemistry , stereochemistry , solvent , organic chemistry , atomic physics , biochemistry , physics , receptor
New ONS hydrazone ligand, 2‐[(2‐aminochromon‐3‐yl)methylidene]‐ N ‐phenylhydrazinecarbothioamide, HL , was synthesized and reacted with different salts of Cu (II) ion (OAc − , NO 3 − , SO 4 2− and Cl − ) in absence and presence of secondary ligands (L′); 8‐hydroxyquinoline, 1,10‐phenanthroline or SCN − ; to form binary and ternary Cu(II)‐chelates. The ligand and its Cu(II)‐complexes were fully characterized by analytical, spectral, thermal, conductivity and magnetic susceptibility measurements. The metal chelates showed octahedral, square planar and /or distorted tetraherdal arrangements. Coats–Redfern equations used to calculate the kinetic parameters of the thermal decomposition stages (E a , A, ΔH, ΔS and ΔG). The compounds exhibit luminescence property; promising interesting potential applications as photoactive materials. Lippert–Mataga, Bakhshiev, Kawski–Chamma–Viallet and microscopic solvent polarity parameter and E T N correlation methods were applied on the solvatochromic shifts of emission spectra to evaluate the ground (μ g ) and excited (μ e ) states dipole moments. Excited state dipole moment is larger than the ground state which may be attributed to π‐π* transition. The coordinating anions play an important role on the position and intensity of emission band. The ligand and its metal complexes showed antimicrobial activity towards Gram–positive bacteria, Gram–negative bacteria, yeast and fungus. The molecular structural parameters of HL and its Cu(II)‐ complexes have been calculated on the basis of DFT engaged in the Gaussian 09 program at the B3LYP/6‐31G(d,p) level; the theoretical data are correlated with the experimental data.