The Bingel-Hirsch reactions on non-isolated pentagon rule (non-IPR) Gd(3)N@C(2n) (2n = 82, 84) are studied. Computational results show that the two metallofullerenes display similar reactivity according to their related topologies. Long C-C bonds with large pyramidalization angles lead to the most stable adducts, the [5,6] bonds in the adjacent pentagon pair being especially favored. The lesser regioselectivity observed for Gd(3)N@C(82) is probably due to the activation of some C-C bonds by means of the metal cluster.