Diphenyl selenoxide: Unraveled peculiarities in methanol and acetonitrile solutions

Abstract

We hereby report the volumetric, spectroscopic (UV–Vis, FTIR), and voltammetric properties together with the comprehensive atomistic simulations of diphenyl selenoxide (Ph2SeO) in acetonitrile (ACN) and methanol (MEOH). The solvation effects manifested through densimetry, UV–Vis, and FTIR spectra have been rationalized for the first time. The anodic oxidation and cathodic reduction of Ph2SeO proceeded more easily in a polar aprotic solvent, such as ACN, compared to a polar protic solvent, such as MEOH. The independent atomistically precise simulation studies examining the universe of the stationary point molecular configurations provided solid proof for a substantially better solvation performance of MEOH relative to ACN. The higher degree of conformational flexibility of the MEOH molecules, their strong hydrogen bonding with the seleneoxide group, and sterical confinement of the electrophilic interaction center of Ph2SeO unraveled via numerous low-energy molecular configurations altogether stand beyond a higher maximum homogeneous concentration of the amphiphilic seleneoxide solute in MEOH than in ACN. The reported results reveal the peculiarities of the diphenyl seleneoxide-containing solutions. They are addressed to the researchers representing the field of solution chemistry.