Resonance
structures provide a handy way of deciding how far delocalization
extends in a molecule. A set of resonance structures for a molecule
must have the atomic nuclei in the same places, and can differ only
in the placement of electrons and hence of bonds and charges. When
all possible resonance structures have been written for a molecule
that cannot be described adequately by simple single and double
bonds, then all atoms that are connected by double bonds in at least
one of the resonance structures are involved in the delocalized
electron system. For benzene these are the six carbon atoms, and
the hydrogens play no part in delocalization. Delocalization in
carbon compounds almost always involves the combination of a set
of p orbitals perpendicular to the plane of a molecular skeleton
connected by s- bonds. The double bonds
do not have to be alternating around a closed ring for delocalization
to occur. In the butadiene molecule shownon the next page, four
carbon atoms are connected in a linear chain with two double bonds.
Structure (b) is the one usually thought of for butadiene, but it
cannot be completely right because all ten atoms in the real molecule
lie in a plane, and this would not necessarily be true if the central
carbon-carbon bond were a single bond.
|
|