Open AccessSynthesis and characterization of four N-acylhydrazones as potential O,N,O donors for Cu2+: An experimental and theoretical study
Author(s) -
Dorian Polo-Cerón,
María Mercedes Hincapié-Otero,
Andrey Joaqui-Joaqui
Publication year - 2021
Publication title -
universitas scientiarum
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.207
H-Index - 10
eISSN - 2027-1352
pISSN - 0122-7483
DOI - 10.11144/javeriana.sc26-2.saco
Subject(s) - chemistry , ligand (biochemistry) , molecule , ab initio , infrared spectroscopy , computational chemistry , ab initio quantum chemistry methods , mass spectrometry , crystallography , organic chemistry , biochemistry , receptor , chromatography
N-acylhydrazones 2-(4-chlorophenyl)-N0 -(2-hydroxybenzylidene)acetohydrazide, N0 -(2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetohydrazide, 2-(4-chlorophenyl)-N0 -(2,4-dihydroxybenzylidene)-acetohydrazide, and N0 -(2,4-dihydroxybenzylidene)-2-(4-methoxyphenyl)acetohydrazide were successfully synthesized by a multistep procedure. The obtained organic molecules were characterized by spectroscopic techniques (FT-IR, 1D and 2D NMR, UV-Vis) and mass spectrometry. The structure of 2-(4-chlorophenyl)-N0 -(2-hydroxybenzylidene)acetohydrazide was also confirmed by X-ray diffraction. Ab initio computational simulations of the ligand spectra were in good agreement with experimental data and validated the hypothesis about the existence of a conformational mixture of each ligand in solution. Finally, the complexation potential of the synthesized ligands to Cu2+ was assessed by continuous variation experiments and FT-IR spectroscopy.