Abstract: Although nitrogen (amine), phosphorus (phosphine), and sulfur (sulfoxide) centered chiral compounds all adopt sp³-hybridized configurations, they demonstrate markedly different energy barriers and rates for configurational inversion, resulting in varying degrees of difficulty in chiral isomer separation. Using these three compound classes as representative examples, this study systematically examines the key factors governing inversion barriers. The analysis reveals that the fundamental distinction originates from the inherent properties of the central atoms, thereby illustrating the foundational principle of organoelement chemistry that “elemental characteristics determine structural and reactivity features”. This work aims to help students develop an electron structure-based approach for understanding structure-reactivity relationships.

Key words: Chiral amines, Chiral phosphines, Chiral sulfoxides, Configuration inversion, Organoelement chemistry