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Hyperconjugation affects several properties. [6] [10]Bond length: Hyperconjugation is suggested as a key factor in shortening of sigma bonds (σ bonds). For example, the single C–C bonds in 1,3-butadiene and propyne are approximately 1.46 Å in length, much less than the value of around 1.54 Å found in saturated hydrocarbons.
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]
Hyperconjugation is also found in acyclic molecules containing heteroatoms, another form of the anomeric effect. If a molecule has an atom with a lone pair of electrons and the adjacent atom is able to accept electrons into the σ* orbital, hyperconjugation occurs, stabilizing the molecule. This forms a "no bond" resonance form.
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 .
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.
This bonding pattern is also seen in trimethylaluminium, which forms a dimer Al 2 (CH 3) 6 with the carbon atoms of two of the methyl groups in bridging positions. This type of bond also occurs in carbon compounds, where it is sometimes referred to as hyperconjugation; another name for asymmetrical three-center two-electron bonds.
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In regards to orbital hybridization, a bond between an sp 2 carbon and an sp 3 carbon is stronger than a bond between two sp 3-hybridized carbons. Computations reveal a dominant stabilizing hyperconjugation effect of 6 kcal/mol per alkyl group. [8]