Title : Synthesis and density functional theory studies of N-heterocyclic carbene derived amide-functionalized organoselenium compounds
Abstract:
The N-heterocyclic carbene (NHC)-selenium framework has emerged as a promising platform for designing organoselenium compounds with potential biomedical applications. In this work, we report an efficient and ecofriendly approach for synthesizing a new series of NHC-derived organoselenium molecules functionalized with amide groups. Starting from an NHC-Se adduct bearing a pendent ester moiety, we achieved a base- and additive-free ester-to-amide transformation under mild conditions. The use of PEG 3550, a biocompatible solvent, significantly improved reaction efficiency and simplified purification, highlighting the method’s sustainability and practical applicability. This strategy accommodates a wide range of aliphatic amines with excellent functional group tolerance, thereby expanding the chemical diversity of organoselenium scaffolds.
To complement experimental findings, density functional theory (DFT) calculations were performed to elucidate electronic structures, stability, and reactivity profiles of the synthesized compounds. Computational insights revealed favorable electronic properties and thermodynamic stability, supporting their potential as candidates for biomedical research. Given selenium’s established role in antioxidant activity and its presence in biologically relevant molecules such as selenoproteins and selenoneine, these newly developed NHC-Se derivatives offer exciting prospects for pharmaceutical development and therapeutic applications.
Overall, this work introduces a straightforward synthetic route combined with theoretical analysis to advance the design of functionalized organoselenium compounds. The findings underscore the synergy between experimental and computational approaches in developing novel molecules with promising biological relevance.
