Chapter 2: Problem 97
An important principle in chemistry is the isolobal analogy. This very simple principle states that chemical fragments with similar valence orbital structures can replace one another in molecules. For example, \(\cdot \dot{\mathrm{C}}-\mathrm{H}\) and \(\cdot \dot{\mathrm{S}}-\mathrm{H}\) are isolobal fragments, each having three electrons with which to form bonds in addition to the bond to \(\mathrm{H}\). An isolobal series of molecules would be HCCH, HCSiH, HSiSiH. Similarly, a lone pair of electrons can be used to replace a bond so that - \(\mathrm{N}\) : is isolobal with \(\cdot \dot{\mathrm{C}}-\mathrm{H}\) with the lone pair taking the place of the \(\mathrm{C}-\mathrm{H}\) bond. The isolobal set here is \(\mathrm{HCCH}, \mathrm{HCN}\), NN. (a) Draw the Lewis structures for the molecules HCCH, HCSiH, HSiSiH, HCN, and NN. (b) Using the isolobal principle, draw Lewis structures for molecules based on the structure of benzene, \(\mathrm{C}_{6} \mathrm{H}_{6}\), in which one or more \(\mathrm{CH}\) groups are replaced with \(\mathrm{N}\) atoms.
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