Exploring acylselenourea diselenides: Synthesis, spectroscopy, and structural characterization of phenyl-substituted N,N'-diselanediyl

Abstract

Acylselenourea diselenides, with the formula [RC(O)NC(Se)NR2]2, are underexplored organoselenated compounds with potential applications in medicinal chemistry, coordination, and organic synthesis. This article presents a comprehensive study on the synthesis, spectroscopy, and structural characterization of the novel diselenide N,N'-diselanediyl-bis-((diphenylamino)methanylylidene)-dibenzamide, i.e., R = Phenyl. The compound was synthesized by a one-pot bimolecular oxidation between the tautomeric forms of the selenourea intermediate PhC(O)NHC(Se)N(Ph)2. The total yield of the reaction was moderate (40 %), with losses attributed to the formation of amorphous red selenium. Spectroscopic analysis, including FT-IR, 1H NMR, and 13C NMR, confirmed the molecular identity of the compound. The crystal structure of diselenide was determined by single-crystal X-ray diffraction analysis, which revealed the formation of a centrosymmetric dimer through a bidirectional hydrogen bond of the C=O···H-Ph type. Hirshfeld surface (HS) analysis and topological study of electron density (ρ) provided detailed information on the strength of the intermolecular and intramolecular interactions in the crystal structure.