Electron deficiency
Electron deficiency occurs when a compound has too few valence electron
Valence electron
In chemistry, valence electrons are the electrons of an atom that can participate in the formation of chemical bonds with other atoms. Valence electrons are the "own" electrons, present in the free neutral atom, that combine with valence electrons of other atoms to form chemical bonds. In a single...

s for the connections between atoms to be described as covalent bond
Covalent bond
A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding....

s. Electron deficient bonds are often better described as 3-center-2-electron bonds. Examples of compounds that are electron deficient are the borane
In chemistry, a borane is a chemical compound of boron and hydrogen. The boranes comprise a large group of compounds with the generic formulae of BxHy. These compounds do not occur in nature. Many of the boranes readily oxidise on contact with air, some violently. The parent member BH3 is called...


The term electron-deficient is also used in a more general way in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

, to indicate a pi-system such as an alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

 or arene
Arene or Arênê or Arène may refer to:*an aromatic hydrocarbon*Arene , a genus of marine snails in the family Areneidae*Arene , the wife of Aphareus and mother of Idas and Lynceus in Greek mythology...

 that has electron-withdrawing groups
Polar effect
The Polar effect or electronic effect in chemistry is the effect exerted by a substituent on modifying electrostatic forces operating on a nearby reaction center...

 attached, as found in nitrobenzene
Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale as a precursor to aniline. Although occasionally used as a flavoring or perfume...

 or acrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...

. Instead of showing the nucleated character common with simple C=C bonds, electron-deficient pi-systems may be electrophilic
In general electrophiles are positively charged species that are attracted to an electron rich centre. In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile...

 and susceptible to nucleophilic attack, as is seen in the Michael addition or in nucleophilic aromatic substitution
Nucleophilic aromatic substitution
right|300px|Aromatic nucleophilic substitutionA nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring...


As the most extreme form of highly localize electron deficiency one can consider the metallic bond
Metallic bond
Metallic bonding is the electrostatic attractive forces between the delocalized electrons, called conduction electrons, gathered in an "electron sea", and the positively charged metal ions...

The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.