The Physical Origin of Saytzeff’s Rule

2009/06/27 by Benoı̂t Braı̈da, Vinca Prana, Philippe C. Hiberty · 1 citation
Chemistry · #Ab initio #Alkene #Catalysis #Chemical Reaction Mechanisms #Chemistry #Computational chemistry #Hyperconjugation #Molecular orbital #Molecule #Organic Chemistry Cycloaddition Reactions #Organic chemistry #Philosophy #Synthesis and Properties of Aromatic Compounds #TRACE (psycholinguistics) #Valence (chemistry) #Valence bond theory

paper · doi:10.1002/anie.200901923

openalex publication_date 2009/06/27 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

Hyperconjugation, hybridization, or what? The hyperconjugative effects in primary, secondary, and tertiary alkenes were estimated using ab initio valence bond methods to trace the origin of the empirical Saytzeff rule, which states that the formation of the more substituted alkene is preferred. Hyperconjugation between the π bond and the π-donating substituents governs Saytzeff's rule, whereas all other factors support an anti-Saytzeff pathway.

Citations

• Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
• The Magnitude of Hyperconjugation in Ethane: A Perspective from Ab Initio Valence Bond Theory

Cited by

• Zaytsev's rule [wikipedia]

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