Molecular orbital
Molecular orbitals are, in general, delocalized throughout the entire molecule. Moreover, if the molecule has symmetry elements, its nondegenerate molecular orbitals are either symmetric or antisymmetric with respect to any of these symmetries. In other words, application of a symmetry operation S (e.g., a reflection, rotation, or inversion) to molecular orbital ψ results in the molecular orbital being unchanged or reversing its mathematical sign: Sψ = ±ψ. In planar molecules, for example, molecular orbitals are either symmetric (sigma) or antisymmetric (pi) with respect to reflection in the molecular plane. If molecules with degenerate orbital energies are also considered, a more general statement that molecular orbitals form bases for the irreducible representations of the molecule's symmetry group holds. The symmetry properties of molecular orbitals means that delocalization is an inherent feature of molecular orbital theory and makes it fundamentally different from (and complementary to) valence bond theory, in which bonds are viewed as localized electron pairs, with allowance for resonance to account for delocalization.