In this review, the authors review and explain their research on "Discovery of Bonding Active Species Containing Nitrogen Atoms" from the past to the present. The authors are interested in new chemical phenomena, especially in the activation of chemical bonds containing nitrogen atoms, and have conducted research to discover chemical bonds with new properties. The activated chemical bonds containing nitrogen atoms are the following (Fig. 1). (1) Rotationally activated C-N bonds by pyramidalization of amide nitrogen atoms (2) N-N bond cleavage ability with reduced bond strength by pyramidalization of nitrosamine nitrogen atoms (3) Transient hetero atom-N bond formation by neighboring group participation of a halogen electron to the nitrogen cation. (4) A unique carbon cation reaction involving nitrogen atoms, especially nitro groups (C-NO2 bond) and ammonium ions (C-NH3+ bond). These purely basic chemistry discoveries unexpectedly led to the creation of functional materials, especially biologically active molecules. We will explain how new chemical bonds led to the creation of new functions.
Keywords: amide; bonding; cations; neighboring group participation; nitrosamine.