Electron deficiency

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Template:Short description In chemistry, electron deficiency (and electron-deficient) is jargon that is used in two contexts: chemical species that violate the octet rule because they have too few valence electrons and species that happen to follow the octet rule but have electron-acceptor properties, forming donor-acceptor charge-transfer salts.

Octet rule violations

File:Structural formula of triphenylborane.svg
Triphenylborane is classified as electron deficient.

Script error: No such module "Labelled list hatnote". Traditionally, "electron-deficiency" is used as a general descriptor for boron hydrides and other molecules which do not have enough valence electrons to form localized (2-centre 2-electron) bonds joining all atoms.[1] For example, diborane (B2H6) would require a minimum of 7 localized bonds with 14 electrons to join all 8 atoms, but there are only 12 valence electrons.[2] A similar situation exists in trimethylaluminium. The electron deficiency in such compounds is similar to metallic bonding.Script error: No such module "Unsubst".

Electron-acceptor molecules

File:PYRTNB03.png
Structure of the charge-transfer complex between pyrene with the electron-deficient 1,3,5-trinitrobenzene.[3]

Alternatively, electron-deficiency describes molecules or ions that function as electron acceptors. Such electron-deficient species obey the octet rule, but they have (usually mild) oxidizing properties.[4] 1,3,5-Trinitrobenzene and related polynitrated aromatic compounds are often described as electron-deficient.[5] Electron deficiency can be measured by linear free-energy relationships: "a strongly negative ρ value indicates a large electron demand at the reaction center, from which it may be concluded that a highly electron-deficient center, perhaps an incipient carbocation, is involved."[6]

References

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Template:Chemical bonds

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