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Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.
Negative hyperconjugation is seldom observed, though it can be most commonly observed when the σ *-orbital is located on certain C–F or C–O bonds. [ 3 ] [ 4 ] In negative hyperconjugation, the electron density flows in the opposite direction (from a π- or p-orbital to an empty σ * -orbital) than it does in the more common ...
Hyperconjugation Carbon radicals are stabilized by hyperconjugation, meaning that more substituted carbons are more stable, and hence have lower BDEs. In 2005, Gronert proposed an alternative hypothesis involving the relief of substituent group steric strain (as opposed to the before accepted paradigm, which suggests that carbon radicals are ...
Hyperconjugation is the stabilizing interaction that results from the interaction of the electrons in a sigma bond (usually C-H or C-C) with an adjacent empty (or partially filled) non-bonding p-orbital or antibonding π orbital or an antibonding sigma orbital to give an extended molecular orbital that increases the stability of the system. [3]
The Cieplak effect relies on the stabilizing interaction of mixing full and empty orbitals to delocalize electrons, known as hyperconjugation. [2] When the highest occupied molecular orbital of one system and the lowest unoccupied molecular orbital of another system have comparable energies and spatial overlap, the electrons can delocalize and sink into a lower energy level.
Hyperconjugation model for explaining the gauche effect in 1,2-difluoroethane. Key in the bent bond explanation of the gauche effect in difluoroethane is the increased p orbital character of both C−F bonds due to the large electronegativity of fluorine. As a result, electron density builds up above and below to the left and right of the ...
However, relatively modest stabilizing effects can render them bound. For example, cyclopropyl and cubyl anions are bound due to increased s character of the lone pair orbital, while neopentyl and phenethyl anions are also bound, as a result of negative hyperconjugation of the lone pair with the β-substituent (n C → σ* C–C).
Negative hyperconjugation is a theorized phenomenon in organosilicon compounds, in which hyperconjugation stabilizes or destabilizes certain accumulations of positive charge. The phenomenon explains corresponding peculiarities in the stereochemistry and rate of hydrolysis .