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negative hyper-conjugation

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.
NT07081
Source:
PAC, 1999, 71, 1919 (Glossary of terms used in theoretical organic chemistry) on page 1954
InChI=1/C2H4F/c1-2-3/h1-2H2/q-1
PHXOVFDNXGUCLW-UHFFFAOYAA
InChI=1/C2H4/c1-2/h1-2H2
VGGSQFUCUMXWEO-UHFFFAOYAE
InChI=1/FH/h1H/p-1/fF/h1h/q-1
KRHYYFGTRYWZRS-SBGXAHRHCZ
InChI=1/CH4FN/c2-1-3/h1,3H2
BYVCDJVESPBRQW-UHFFFAOYAF
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.NT07081.
Original PDF version: http://www.iupac.org/goldbook/NT07081.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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