The effect of donation of electron density from filled π or nπ
-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.
PAC, 1999, 71, 1919. (Glossary of terms used in theoretical organic chemistry
) on page 1954 [Terms