Synthesis, spectroscopic characterization, X-ray structures, biological screenings, DNA interaction study and catalytic activity of organotin(IV) 3-(4-flourophenyl)-2-methylacrylic acid derivatives

A series of organotin(IV) carboxylate complexes [Me2SnL2] (1), [Bu2SnL2] (2), [Oct2SnL2] (3), [Me3SnL] (4), [Bu3SnL] (5) and [Ph3SnL] (6), where L = O2C(CH3)CCHC6H4F have been successfully synthesized and characterized by FT-IR, NMR (1H, 13C) and single crystal analysis. The ligand coordinates to tin atom via carboxylate group. Compound 1 and 4 have also been studied by single crystal XRD analysis. The synthesized compounds were screened for their biological activities including anti-bacterial, anti-fungal, anti-tumor and cytotoxicity. The compounds 4–6 exhibit excellent anti-bacterial, anti-fungal and anti-tumor activities. The ligand binds with DNA double helix by hydrogen bonding between the ligand and the base pairs in DNA typically to N3 of adenine and O2 of thymine as well as partial intercalation of aromatic ring into the base pairs of DNA. The complexes also interact with DNA via intercalation of aromatic ring into the base pairs of DNA. The catalytic activity of compounds 46 was assessed in transesterification of triglycerides in rocket seed oil into biodiesel. The choice of these compounds is the Lewis acid nature of tin atom. The samples were taken in regular interval of 1, 8, 16 and 24 h and % age conversion was determined by 1H NMR. All the tested compounds showed good catalytic activity in the order 4 > 5 > 6.

The title complex was synthesized by the reaction of the sodium salt R/COONa (R=(CH3)CCHC6H4F) with dimethyltin(IV) dichloride in 2:1 molar ratios in dry toluene in a 250 mL two necked round bottom flask.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of new six organotin(IV) carboxylate complexes.
► Spectroscopic characterization by FT-IR, NMR (1H &13C) and Single XRD analysis.
►  Interaction of compounds with SS-DNA.
► Biological screenings (antimicrobial, cytotoxicity and antitumor activities).
► Assessment of catalytic activity in transesterification of oil into biodiesel.