Hyperconjugation

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Hyperconjugation in organic chemistry 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 to give an extended molecular orbital that increases the stability of the system. Only electrons in bonds that are β to the positively charged carbon can stabilize a carbocation by hyperconjugation.

Hyperconjugation can be used for rationalizing 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. Hyperconjugation has also been shown to be the correct explanation for the preference of the staggered conformation rather than the old textbook notion of steric hindrance. [1] [2].

External links

References

  1. Hyperconjugation not steric repulsion leads to the staggered structure of ethane Pophristic, V. & Goodman, L. Nature 411, 565–568 (2001)Abstract
  2. Chemistry: A new twist on molecular shape Frank Weinhold Nature 411, 539-541 (31 May 2001)

See also

de:Hyperkonjugation nl:Hyperconjugatie


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