A general description of phosphorus containing functional groups

Phosphorus containing functional groups induce an important stabilizing effect on adjacent carbanions. Such an interaction is, however, not observed for the neutral compounds. Using computational methods, we clarify the fundamental properties of these functional groups that lead to these differences. By doing so, a general description of phosphorus containing functional groups of the –PY2 and –POY2 type is obtained. These groups should be seen as highly ionic groups having a σ donor/π acceptor character.