In organic chemistry, negative hyperconjugation is the donation of electron density from a filled π- or p-orbital to a neighboring σ*-orbital.[1] This phenomenon, a type of resonance, can stabilize the molecule or transition state.[2] It also causes an elongation of the σ-bond by adding electron density to its antibonding orbital.[1]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/b/b8/NegativeHyperconjugation-8.svg/350px-NegativeHyperconjugation-8.svg.png)
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 (from a σ-orbital to an empty p-orbital).
See also
References
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