text: The convergence of observed BD angles can be viewed as arising from the need to maximize overlap between the highest occupied molecular orbital (HOMO) of the nucleophile, and the lowest unoccupied molecular orbital (LUMO) of the unsaturated, trigonal center of the electrophile. (See, in comparison, the related inorganic chemistry concept of the angular overlap model.)
  In the case of addition to a carbonyl, the HOMO is often a p-type orbital (e.g., on an amine nitrogen or halide anion), and the LUMO is generally understood to be the antibonding π* molecular orbital perpendicular to the plane containing the ketone C=O bond and its substituents (see figure at right above). The BD angle observed for nucleophilic attack is believed to approach the angle that would produce optimal overlap between HOMO and LUMO (based on the principle of the lowering of resulting new molecular orbital energies after such mixing of orbitals of similar energy and symmetry from the participating reactants). At the same time, the nucleophile avoids overlap with other orbitals of the electrophilic group that are unfavorable for bond formation (not apparent in image at right, above, because of the simplicity of the R=R'=H in formaldehyde).