Synthesis, X-ray, DFT and photophysical properties of some new ferrocenyl hydrazono thiazolidin-4-ones and their derivatives

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 143; pp. 256 - 264
• Main Authors: Gautam, Deepika, Chaudhary, R.P.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 15.05.2015
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Crystallography, X-Ray; DFT; Ferrocenylthiazolidin-4-one; Ferrous Compounds - chemical synthesis; Ferrous Compounds - chemistry; Ferrous Compounds - pharmacology; Fluorescence; Hydrazones - chemical synthesis; Hydrazones - chemistry; Hydrazones - pharmacology; Models, Molecular; Molecular Structure; Quantum Theory; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Stereoisomerism; Thiazole; Thiazolidines - chemical synthesis; Thiazolidines - chemistry; Thiazolidines - pharmacology; Thiosemicarbazone; X-ray diffraction; X-ray diffraction; Fluorescence; DFT; Thiosemicarbazone; Thiazole; Ferrocenylthiazolidin-4-one
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2015.01.123

[Display omitted] •New ferrocenyl hydrazono thiazolidin-4-one derivatives have been synthesised.•Characterization of new compounds is done by analytical and spectral data.•X-ray diffraction studies of ferrocenyl hydarazono thiazolidin-4-one are reported.•Proton and carbon NMR data from DFT studies is compared with experimental results.•UV/visible absorption, fluorescence and antimicrobial studies are reported. Cyclocondensation of thiosemicarbazone of 2-acetylferrocene with α-haloacids and α-haloketones afford new ferrocenyl hydrazono thiazolidin-4-ones and ferrocenyl hydrazono thiazoles respectively. Ferrocenyl hydrazono thiazolidin-4-one is easily converted into enamino ketone with N,N-dimethylformamide dimethyl acetal (DMF-DMA). The compounds were characterized by spectroscopic means and the structure of the new ferrocenyl hydrazono thiazolidin-4-one (3a) was determined by means of X-ray crystallography. The photophysical properties of these compounds were studied by means of UV/visible absorption spectroscopy and fluorescence spectroscopy. Density functional theory (DFT) calculations have been carried out with Gaussian 09W using B3LYP density functional method and 6-31G (d) basis set. 1H and 13C Nuclear Magnetic Resonance (NMR) have been calculated and correlated with experimental results. Antimicrobial activity studies of some new compounds have been reported.