In MO theory a bond is formed when atomic orbitals of similar energy
and symmetry combine to form at least one molecular orbital of lower
energy than that of the isolated AO's, and when that bonding MO
then is filled by a pair of electrons. In principle, all bonds extend
over the entire molecule, but in practice it is usually possible
to consider only two atoms at a time, and to think of the bond between
them as being independent of all other bonds in the molecule. This
localized-bond picture sometimes fails us, especially when p orbitals
are involved in delocalization along chains or rings of carbon atoms.
When this occurs, the molecular skeleton can be treated as a set
of a- bonds, and the p orbitals can be treated separately. The filled
inner shells in atoms can be ignored in bonding, and only the outer
orbitals and outer-shell electrons need be considered. In localized,
two-atom bonds, the s and three p atomic orbitals usually are not
the best starting points in bonding. All four orbitals can be hybridized,
before they are combined with orbitals from other atoms, to produce
a set of four identical sp3 hybrid orbitals pointing in tetrahedral
directions. Alternatively, the s and two of the p orbitals can be
hybridized into three Sp2 orbitals 120 apart
in a plane; or the s and one p can be combined into two sp orbitals
pointing in opposite directions from the atom. The best hybridization
to use depends on the actual geometry of the molecule, and on the
presence of double or triple bonds.
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