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Experimental and DFT studies of hydrogen bonds in salicylaldehyde-4-phenylthiosemicarbazone

Thiosemicarbazones and their metal complexes have attracted much interest nowdays owing to their chemical and biochemical significance. It was demonstrated that they exhibited biological activity as anti-cancer, anti-viral, anti-bacterial and anti-fungal agents. Salicylaldehyde-4-phenylthiosemicarbazone (SALTSC-4Ph) posseses several proton-donor and proton-acceptor groups and therefore can form both intra- and inter-molecular hydrogen bonds. Exploring H-bond structure of SALTSC-4Ph makes a significant contribution to understanding of its bioactivity. The results of H-bonding interaction studies in both protonated and deuteriated (OH and OD) SALTSC-4Ph are reported. A combination of experimental and theoretical methods enabled a straightforward assignment of vibrational modes in IR and Raman spectra and elucidated the nature of H-bonds in solution. Investigation of deuterium isotope effects in NMR spectra gave further insight into these interactions. Quantum chemical calculations at the B3LYP/6-31G* level including the explicit solvent molecule were performed. Apart from intramolecular H-bonds, SALTSC-4Ph was also found to form stable complexes with acetone and DMSO molecules.

hydrogen bonds; salicylaldehyde-4-phenylthiosemicarbazone; NMR; DFT

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