A Planar Five-Membered Aromatic Ring Stabilized by Only Two π-Electrons.

Many chemicals known today are partially or fully aromatic, since a ring framework experiences additional stabilization through the delocalization of π-electrons. While aromatic rings with equal numbers of π-electrons and ring atoms such as benzene are particularly stable, those with the minimally required two π-electrons are very rare and yet remain limited to three- and four-membered rings if not stabilized in the coordination sphere of heavy metals. Here we report the facile synthesis of a dipotassium cyclopentagallene, a unique example of a five-membered aromatic ring stabilized by only two π-electrons. Single-crystal X-ray diffraction revealed a planar Ga 5 ring with almost equal gallium-gallium bond lengths, which together with computational and spectroscopic data confirm its aromatic character. Our results prove that aromatic stabilization goes far beyond what has previously been assumed as minimum π-electron count in a five-atom ring fragment.