How the Misuse of Symmetry Can Obscure the Underlying Science

Hybridization and Valence Shell Electron Pair Repulsion (VSEPR) theory, and its underlying symmetry, are invaluable aids to quickly assign bond angles around individual second row atoms within a molecule. In the cases of oxygen and nitrogen atoms, this can lead to false conclusions as to an appropriate atomic orbital hybridization and local symmetry of those orbitals when compared to experimental finding. This becomes most evident when an extended conjugation of a lone pair of electrons on nitrogen or oxygen creates a situation that “breaks the rules” of hybridization. A method of introducing hybridization other than sp3 for nitrogens and oxygens, which are “neighbors” to a double bond is presented.