An important principle in chemistry is the isolobal analogy. This very simple
principle states that chemical fragments with similar valence orbital
structures can replace each other in molecules. For example, \(\cdot
\mathrm{C}-\mathrm{H}\) and \(\cdot \mathrm{S}-\mathrm{H}\) are isolobal
fragments, cach having three electrons with which to form bonds besides the
bond to \(\mathrm{H}\). An isolobal series of molecules would be HCCH, HCSiH,
and HSiSiH. Similarly, a lone pair of clectrons can be used to replace a bond
so that - \(\mathrm{N}\) : is isolobal with ' \(\mathrm{C}-\mathrm{H}\), with the
lone pair taking the place of the \(\mathrm{C}-\mathrm{H}\) bond. The isolobal
set here is HOCH, HCN, and NN. (a) Draw the Lewis structures for the molecules
HCCH, HCSiH, HSiSiH, \(\mathrm{HCN}\), and NN. (b) Using the isolobal principle,
draw Lewis structures for molecules based on the structure of benzenc,
\(\mathrm{C}_{6} \mathrm{H}_{6}\), in which one or more \(\mathrm{CH}\) groups are
replaced with \(\mathrm{N}\) atoms.