ABSTRACT
The N, N'-(1,2-phenylene) bis (1- (4- chlorophenyl) methanimine) (CS4) was synthesized and characterized by infrared (IR), absorption (UV-vis) and NMR (1H and 13C) spectral analyses. The structural parameters, vibrational frequencies, potential energy and the distribution analysis (PED) were calculated by using DFT with the basis set of B3LYP/cc-pVDZ and these spectral values were compared to the experimental values. HOMO and LUMO studied were performed in order to understand the stability and biological activity of the compound. The most reactive sites on the compound were investigated by utilizing MEP energy surface and Fukui function descriptor with the natural population analysis (NPA) of the charges. The study of the natural bond orbitals (NBO) reveals the delocalization of the intramolecular interaction of the charges in the compound. Additionally, topological investigations (ELF, LOL), determination of thermodynamic parameters and noncovalent interaction (NCI) study by using topology (RDG) analysis were also carried out. Finally, the molecular docking and molecular dynamics simulations was carried out by examining against glycosylphosphatidylinositol phospholipase D inhibitor receptor for distinct protein targets (3MZG).Communicated by Ramaswamy H. Sarma.
ABSTRACT
Benzo[4,5]thiazolo[3, 2-a]pyrimidine-3-carboxylate derivatives (4a-i) containing electron-donor and electron-acceptor groups with remarkable photophysical and electrochemical properties were synthesized. The changes in absorption properties of compound 4a in the presence of various cations were evaluated. Compound 4a can act as a colorimetric sensor for highly sensitive and selective detection of Fe3+ and Cr3+in acetonitrile solvent. Using measurements of absorbance intensity, the binding constants for the 4a + Fe3+ complex and 4a + Cr3+ complex were found to be 1.958 × 108 and 1.5442 × 107 M-1 with lower detection limits of 52 and 110 nM, respectively. 1H NMR titrations, Fourier transform infrared (FTIR) studies, electrospray ionization (ESI)-mass spectra, and Job's plots were used to verify the mechanism of the specific reaction and colorimetric sensing of 4a + Fe3+ and 4a + Cr3+. The application of compound 4a for the determination of Fe3+ in spiked samples of iron tablets in different environmental water samples showed a satisfactory result with good recovery.
