Abstract

The thermodynamic and kinetic stability of bis(diisopropylamino)cyclopropenylidene and related molecules were investigated by quantum chemical methods. The main stabilizing factor in the amino-substituted cyclopropenylidene is the significant pi-electron shift from the amino substituents, via a nonaromatic ylidic structure; however, its successful synthesis is based on its high kinetic stability. The silicon and germanium analogues show lower stabilization than the synthesized carbene. However, when investigating their reactions, we found that both amino-disubstituted three-membered silylene and germylene have considerable kinetic stability.