Orbital hybridization: a key electronic factor in control of structure and reactivity

This review outlines fundamental factors responsible for hybridization trends in organic and main group compounds. Hybridization is a classic chemical concept that transcends textbook organic chemistry. Hybridization effects are omnipresent, and their understanding is essential for the unraveling of many structural and reactivity puzzles. Even when they are masked by a stronger effect (e.g., allylic delocalization), they still lurk below the surface. Overriding such effects comes with a penalty, whereas incorporation into reaction design provides an efficient tool for the control of reactivity. Copyright © 2014 John Wiley & Sons, Ltd. This review outlines fundamental factors responsible for hybridization trends in organic and main group compounds. Hybridization effects are omnipresent, and their understanding is essential for the unraveling of many structural and reactivity puzzles. Even when they are masked by a stronger effect, they still lurk below the surface.