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

• Published in: Journal of physical organic chemistry Vol. 28; no. 2; pp. 147 - 162
• Main Authors: Alabugin, Igor V., Bresch, Stefan, dos Passos Gomes, Gabriel
• Format: Journal Article
• Language: English
• Published: Bognor Regis Blackwell Publishing Ltd 01.02.2015; Wiley Subscription Services, Inc
• Subjects: Bent's rule; conjugation/hyperconjugation; hybridization; reactivity/structure; rehybridization
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.3382

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.