LAUSR

Abstract In this joint experimental-DFT study, we present a robust synthetic methodology, designed to produce Se-Cn-Se and C–Se–C. Three pyridyl based selenoethers were synthesized, characterized and analyzed by applying Density Functional Theory (DFT) calculations and conducting cyclic voltammetry (CV) experiments. Bis(2-(pyridin-2-yl)ethyl)selane (BPSe), 1,3-bis((2-(pyridin-2-yl)ethyl)selanyl)propane (BP3Se2) and 1,4-bis((2-(pyridin-2-yl)ethyl)selanyl)butane (BP4Se2) were synthesized from different selenocyanates and characterized by FT-IR and 13C, 1H, 77Se NMR spectroscopies and mass spectrometry. DFT (B3PW91/6-311G(2df,p)) optimized geometries and spectra simulations concur well with the experimental data. Theoretical reactivity behavior was assessed, taking into account HOMO-LUMO diagrams and Molecular Electrostatic Potential maps. Cyclic voltammetry experiments reveal that C–Se bond cleavage occurs in the reduction reaction, whereas, the selenium compounds manifest typical two-electron oxidation behavior. In this work, pyridyl rings were selected to act as electrophile fragments, but from a perspective which considers the possibility of using many other electrophiles to implement this novel procedure.