Analysis of Hückel's [4n + 2] rule through electronic delocalization measures.
In the present work, we analyze the pi-electronic delocalization in a series of annulenes and their dications and dianions by using electron delocalization indices calculated in the framework of the quantum theory of atoms in molecules. The aim of our study is to discuss the Hückel's 4n + 2 rule from the viewpoint of pi-electronic delocalization. Our results show that there is an important increase of electronic delocalization (of about 1 e) when going from antiaromatic 4n pi systems to aromatic (4n + 2)pi systems. Less clear is the change in pi-electronic delocalization when we move from a (4n + 2)pi-aromatic to a 4n pi-antiaromatic species by adding or removing a pair of electrons.
Institut de Química Computacional and Departament de Química, Campus de Montilivi, 17071 Girona, Catalonia, Spain.
Ferran
F
Feixas
Eduard
E
Matito
Miquel
M
Solà
Jordi
J
Poater