Synthesis, X-ray, DFT and photophysical properties of some new ferrocenyl hydrazono thiazolidin-4-ones and their derivatives.
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. (1)H and (13)C Nuclear Magnetic Resonance (NMR) have been calculated and correlated with experimental results. Antimicrobial activity studies of some new compounds have been reported.
Department of Chemistry, Sant Longowal Institute of Engineering & Technology, Longowal (Sangrur), Punjab 148106, India.
Deepika
D
Gautam
Department of Chemistry, Sant Longowal Institute of Engineering & Technology, Longowal (Sangrur), Punjab 148106, India. Electronic address: rpchaudhary65@gmail.com.
R P
RP
Chaudhary
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D005296:Ferrous Compounds; D006835:Hydrazones; D053778:Thiazolidines; C000604664:ferrocenyl hydrazono thiazolidin-4-one
DFT; Ferrocenylthiazolidin-4-one; Fluorescence; Thiazole; Thiosemicarbazone; X-ray diffraction