S. Nagaraju, M. A. Sridhar, N. R. Sreenatha
Apr 10, 2018
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X-ray Structure Analysis Online
Abstract
Thiophene is a five-membered, sulfur-containing hetero aromatic ring. Its nucleus has been one of the most important potential entities in the rapidly growing chemical world of heterocyclic compounds during the last few decades due to diverse applications in material science and pharmaceuticals. Substituted thiophenes have exhibited a wide spectrum of biological activities, ranging from antibacterial, antifungal, antioxidant, antivirus, antianxiety, antiprotozoal, insecticidal, antiproliferative and herbicide.1–3 Moreover, polymeric thiophenes are also broadly utilized as thin-film transistors, organic field-effect transistors, organic light-emitting transistors (OLET), chemical sensors, and solar cells.4–7 In view of the above mentioned importance, the synthesis and crystal structure of the title compound (4-fluorophenyl)(2-(methylthio)thiophen3-yl)methanone is reported here. The compound 1-(4-fluorophenyl)-3-((2,2-diethoxyethyl)thio)-3-(methylthio)prop-2-en-1-one was taken into a roundbottomed flask and mixed with 5 mL of dry ethanol, followed by orthophosphoric acid (5 mL). The reaction mixture was heated for a period of 80 min at 80°C. The progress of the reaction was monitored by TLC (EtOAc:pet.ether, 2:8), and the reaction mixture was concentrated in a rotary evaporator. Further, the concentrated reaction mixture was poured into icecold water and extracted with ethyl acetate and dried (Na2SO4); the solvent was distilled out in a rotary evaporator. The residue obtained was purified by passing through silica gel and then eluted with 5% ethyl acetate and petroleum ether to yield the product (4-fluorophenyl)(2-(methylthio)thiophen-3-yl)methanone and recrystalized by ethanol. A schematic diagram of the synthesis of the title compound is shown in Fig. 1. A yellow block-shaped crystal of the title compound, C12H9FOS2 with dimensions of 0.25 × 0.23 × 0.21 mm3, was chosen for an X-ray diffraction study using a Bruker X8 Proteum diffractometer equipped with Cu Kα radiation (λ = 1.54178 Å) at 296 K. Data collection, integration, and scaling of the reflections were performed using the APEX2 program.8 2018 © The Japan Society for Analytical Chemistry