Hyperconjugation

This review outlines the role of hyperconjugative interactions in the structure and reactivity of organic molecules. After defining the common hyperconjugative patterns, we discuss the main factors controlling the magnitude of hyperconjugative effects, including orbital symmetry, energy gap, electro...

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Bibliographic Details
Published in:Wiley interdisciplinary reviews. Computational molecular science 2019-03, Vol.9 (2), p.e1389-n/a
Main Authors: Alabugin, Igor V., dos Passos Gomes, Gabriel, Abdo, Miguel A.
Format: Article
Language:English
Subjects:
bond theory
Catalysis
Catalysts
Control stability
delocalization
Electronegativity
Energy gap
Hazards
hyperconjugation
Interactions
Modelling
Molecular modelling
Molecular structure
orbital
Organic chemistry
Polarizability
Reaction mechanisms
stereoelectronic effects
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Summary:This review outlines the role of hyperconjugative interactions in the structure and reactivity of organic molecules. After defining the common hyperconjugative patterns, we discuss the main factors controlling the magnitude of hyperconjugative effects, including orbital symmetry, energy gap, electronegativity, and polarizability. The danger of underestimating the contribution of hyperconjugative interactions are illustrated by a number of spectroscopic, conformational, and structural effects. The stereoelectronic nature of hyperconjugation offers useful ways for control of molecular stability and reactivity. New manifestations of hyperconjugative effects continue to be uncovered by theory and experiments. This article is categorized under: Structure and Mechanism > Molecular Structures Software > Molecular Modeling Structure and Mechanism > Reaction Mechanisms and Catalysis This review outlines the role of hyperconjugative interactions in the structure and reactivity of organic molecules. After defining the common hyperconjugative patterns, we discuss the main factors controlling the magnitude of hyperconjugative effects, including orbital symmetry, energy gap, electronegativity, and polarizability. The danger of underestimating the contribution of hyperconjugative interactions are illustrated by a number of spectroscopic, conformational, and structural effects. The stereoelectronic nature of hyperconjugation offers useful ways for control of molecular stability and reactivity. New manifestations of hyperconjugative effects continue to be uncovered by theory and experiments.
ISSN:1759-0876
1759-0884
DOI:10.1002/wcms.1389