Electrophile

electrophilicelectrophileselectrophilicitysuperelectrophile electrophilic characterelectron-poor areasElectrophiliaelectrophilic siteelectrophilic specieselectrophilically
In organic chemistry, an electrophile is an electron pair acceptor.wikipedia
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Nucleophile

nucleophilicnucleophilic attacknucleophilicity
It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile.
The terms nucleophile and electrophile were introduced by Christopher Kelk Ingold in 1933, replacing the terms anionoid and cationoid proposed earlier by A. J. Lapworth in 1925.

Lewis acids and bases

Lewis acidLewis baseLewis acids
Because electrophiles accept electrons, they are Lewis acids (see acid-base reaction theories).
The terms nucleophile and electrophile are more or less interchangeable with Lewis base and Lewis acid, respectively.

Carbonyl group

carbonylcarbonyl compoundcarbonyls
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.
This relative electronegativity draws electron density away from carbon, increasing the bond's polarity, therefore making carbon an electrophile (i.e. slightly positive).

Chlorine

Clchlorine gaschlorinated
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.
Due to the difference of electronegativity between chlorine (3.16) and carbon (2.55), the carbon in a C–Cl bond is electron-deficient and thus electrophilic.

Ethylene

etheneC 2 H 4 ethylene gas
For example, ethene + bromine → 1,2-dibromoethane:
The double bond is a region of high electron density, thus it is susceptible to attack by electrophiles.

Carbene

carbenesalkylideneCarbene Chemistry
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.
Singlet carbenes generally participate in cheletropic reactions as either electrophiles or nucleophiles.

Halogen addition reaction

adds across carbon carbon double bondsbromine addition reactiondihalo addition reaction
These occur between alkenes and electrophiles, often halogens as in halogen addition reactions.
The atom is electrophilic at this time and is attacked by the pi electrons of the alkene [carbon–carbon double bond].

Bromine

Brbrominatedbromo
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL. For example, ethene + bromine → 1,2-dibromoethane:
Due to the difference of electronegativity between bromine (2.96) and carbon (2.55), the carbon in a C–Br bond is electron-deficient and thus electrophilic.

Halonium ion

bromoniumbromonium ioniodonium
These ions are usually only short-lived reaction intermediates; they are very reactive, owing to high ring strain in the three-membered ring and the positive charge on the halogen; this positive charge makes them great electrophiles.

Ketone

ketonesketoketo group
The Shi catalyst, a ketone, is oxidized by stoichiometric oxone to the active dioxirane form before proceeding in the catalytic cycle.
Thus, ketones are nucleophilic at oxygen and electrophilic at carbon.

Oxaziridine

Sulfonyloxaziridine enolate oxidationcamphorsulfonyl oxaziridineDavis’ oxaziridine
Oxaziridines such as chiral N-sulfonyloxaziridines effect enantioselective ketone alpha oxidation en route to the AB-ring segments of various natural products, including γ-rhodomycionone and α-citromycinone.
Whereas oxygen and nitrogen typically act as nucleophiles due to their high electronegativity, oxaziridines allow for electrophilic transfer of both heteroatoms.

Peroxy acid

peracidperoxyacidperacids
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.
Electrophilic peroxides are stronger oxygen-atom transfer agents.

Diisobutylaluminium hydride

DIBALDIBAL-Hdiisobutylaluminum hydride
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.
Thus, it is an electrophilic reducing agent whereas LiAlH 4 can be thought of as a nucleophilic reducing agent.

Nitronium ion

nitroniumNO 2 + NO
In gitionic (gitonic) superelectrophiles, charged centers are separated by no more than one atom, for example, the protonitronium ion O=N + =O + —H (a protonated nitronium ion).
It is stable enough to exist in normal conditions, but it is generally reactive and used extensively as an electrophile in the nitration of other substances.

Selectfluor

F-TEDA-BF 4
And, in distonic superelectrophiles, they are separated by 2 or more atoms, for example, in the fluorination reagent F-TEDA-BF 4.
The conventional source of "electrophilic fluorine", i.e. the equivalent to the superelectrophile F +, is gaseous fluorine, which requires specialised equipment for manipulation.

Chemistry

chemistchemicalApplied Chemistry
chemistry, an electrophile is an electron pair acceptor.

Electron pair

Lewis pairunpairedelectron pairs
It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile.

Chemical bond

bondbondschemical bonds
It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile.

Acid–base reaction

acid-base reactionacid-baseacid-base chemistry
Because electrophiles accept electrons, they are Lewis acids (see acid-base reaction theories).

Electric charge

chargeelectrical chargecharged
Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.

Organic synthesis

synthesissynthesizedsynthetic
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.

Ion

cationanionions
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.

Hydrogen ion

H + Hhydrogen ions
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.

Nitrosonium

nitrosonium ionNO +
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.

Hydrogen chloride

HClanhydrous hydrochloric acidHCl gas
The electrophiles frequently seen in the organic syntheses are cations such as H + and NO +, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl 2 and Br 2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH 3 and DIBAL.