The effect of donation of electron density from filled π or n
π-orbitals to the symmetry adapted σ*-orbital(s) of σ-bond(s) of a molecular entity resulting in building π-character into bonds that nominally possess only σ-character. The consequences of the effect are, for example, in elongation of the
C–F bond in the β-fluoroethyl anion and stabilization of the anti-periplanar conformation of fluoromethylamine.
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Source:
PAC, 1999, 71, 1919. 'Glossary of terms used in theoretical organic chemistry' on page 1954 (https://doi.org/10.1351/pac199971101919)