Nucleophile

nucleophilicnucleophilic attacknucleophilicitynucleophilesambident nucleophileattacksnucleophilic reagents nucleophilicallyattackedelectron donor
A nucleophile is a chemical species that donates an electron pair to form a chemical bond in relation to a reaction.wikipedia
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Electrophile

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

Solvolysis

alcoholysisacetolysisammonolysis
Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis.
Solvolysis is a type of nucleophilic substitution (S N 1) /( S N 2) or elimination, where the nucleophile is a solvent molecule.

Christopher Kelk Ingold

Christopher IngoldSir Christopher IngoldC. K. Ingold
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.
His groundbreaking work in the 1920s and 1930s on reaction mechanisms and the electronic structure of organic compounds was responsible for the introduction into mainstream chemistry of concepts such as nucleophile, electrophile, inductive and resonance effects, and such descriptors as S N 1, S N 2, E1, and E2.

Alpha effect

α-effect
Nucleophiles displaying the so-called alpha effect are usually omitted in this type of treatment.
The alpha effect refers to the increased nucleophilicity of an atom due to the presence of an adjacent (alpha) atom with lone pair electrons.

Hydroxide

OHhydroxide ionOH −
This treatment results in the following values for typical nucleophilic anions: acetate 2.7, chloride 3.0, azide 4.0, hydroxide 4.2, aniline 4.5, iodide 5.0, and thiosulfate 6.4. Examples of oxygen nucleophiles are water (H 2 O), hydroxide anion, alcohols, alkoxide anions, hydrogen peroxide, and carboxylate anions.
It functions as a base, a ligand, a nucleophile, and a catalyst.

Nucleophilic substitution

nucleophilic displacementnucleophilic aliphatic substitutionnucleophilic attack
Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge.
In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group; the positive or partially positive atom is referred to as an electrophile.

-phil-

-philiaphilia-phile
The word nucleophile is derived from nucleus and the Greek word φιλος, philos for love.

Chemical reaction

reactionchemical reactionsreactions
A nucleophile is a chemical species that donates an electron pair to form a chemical bond in relation to a reaction.
In the first type, a nucleophile, an atom or molecule with an excess of electrons and thus a negative charge or partial charge, replaces another atom or part of the "substrate" molecule.

Epoxide

epoxidationepoxidesepoxidized
Typical substrate constants are 0.66 for ethyl tosylate, 0.77 for β-propiolactone, 1.00 for 2,3-epoxypropanol, 0.87 for benzyl chloride, and 1.43 for benzoyl chloride.
The peroxide is viewed as an electrophile, and the alkene a nucleophile.

Cyanide

cyanocyanogenicCN
Typical Ritchie N + values (in methanol) are: 0.5 for methanol, 5.9 for the cyanide anion, 7.5 for the methoxide anion, 8.5 for the azide anion, and 10.7 for the thiophenol anion.

Electron pair

Lewis pairunpairedelectron pairs
A nucleophile is a chemical species that donates an electron pair to form a chemical bond in relation to a reaction.

Rate equation

first-order kineticsrate lawfirst-order reaction
This free-energy relationship relates the pseudo first order reaction rate constant (in water at 25 °C), k, of a reaction, normalized to the reaction rate, k 0, of a standard reaction with water as the nucleophile, to a nucleophilic constant n for a given nucleophile and a substrate constant s that depends on the sensitivity of a substrate to nucleophilic attack (defined as 1 for methyl bromide).
For example, in the reaction of aryldiazonium ions with nucleophiles in aqueous solution ArN 2 + + X − → ArX + N 2, the rate equation is v = k[ArN 2 + ], where Ar indicates an aryl group.

Organolithium reagent

organolithiumorganolithium compoundalkyllithium
Carbon nucleophiles are often organometallic reagents such as those found in the Grignard reaction, Blaise reaction, Reformatsky reaction, and Barbier reaction or reactions involving organolithium reagents and acetylides.
Owing to the polar nature of the C-Li bond, organolithium reagents are good nucleophiles and strong bases.

Nucleophilic addition

nucleophilic1,2-additionaddition
These reagents are often used to perform nucleophilic additions.
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electron-deficient or electrophilic double or triple bond, a π bond, reacts with electron-rich reactant, termed a nucleophile, with disappearance of the double bond and creation of two new single, or σ, bonds.

Carbocation

carbocationscarbocationiccarbocation rearrangements
In the original publication the data were obtained by reactions of selected nucleophiles with selected electrophilic carbocations such as tropylium or diazonium cations:
In terms of reactivity, carbocations are susceptible to attack by nucleophiles, like water, alcohols, carboxylates, azide, and halide ions, to form the addition product.

Kolbe nitrile synthesis

electrophilic alkylations at free CN −
Similar considerations apply in the Kolbe nitrile synthesis.
A side product for this reaction is the formation of an isonitrile because the cyanide ion is an ambident nucleophile and according to Kornblum's rule is capable of reacting with either carbon or nitrogen.

Alkoxide

alkoxidesethoxidemetal alkoxide
Examples of oxygen nucleophiles are water (H 2 O), hydroxide anion, alcohols, alkoxide anions, hydrogen peroxide, and carboxylate anions.
Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands.

Piperidine

piperidinespiperidinylNC5H10
With E = −9.15 for the S-methyldibenzothiophenium ion, typical nucleophile values N (s) are 15.63 (0.64) for piperidine, 10.49 (0.68) for methoxide, and 5.20 (0.89) for water.
The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is a highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.

Aldol condensation

Claisen–Schmidt condensationaldolClaisen-Schmidt condensation
Enols are commonly used in condensation reactions, including the Claisen condensation and the aldol condensation reactions.
In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals.

Reactivity–selectivity principle

selectivity
The equation states that two nucleophiles react with the same relative reactivity regardless of the nature of the electrophile, which is in violation of the reactivity–selectivity principle.
With the nucleophilic carbon radical on the other hand both enthalpy and polar effects have the same direction thus extending the activation energy range.

Claisen condensation

ClaisenAcetoacetic ester condensationC-C condensations
Enols are commonly used in condensation reactions, including the Claisen condensation and the aldol condensation reactions.
The base used must not interfere with the reaction by undergoing nucleophilic substitution or addition with a carbonyl carbon.

Nucleophilic abstraction

Nucleophilic abstraction is a type of an organometallic reaction which can be defined as a nucleophilic attack on a ligand which causes part or all of the original ligand to be removed from the metal along with the nucleophile.

Haloalkane

alkyl halidealkyl halideshalogenated hydrocarbons
In the example below, the oxygen of the hydroxide ion donates an electron pair to form a new chemical bond with the carbon at the end of the bromopropane molecule.
Haloalkanes are reactive towards nucleophiles.

Ammonia

NH 3 anhydrous ammonialiquid ammonia
Nitrogen nucleophiles include ammonia, azide, amines, nitrites, hydroxylamine, hydrazine, carbazide, phenylhydrazine, semicarbazide, and amide.
In organic chemistry, ammonia can act as a nucleophile in substitution reactions.

Lewis acids and bases

Lewis acidLewis baseLewis acids
Because nucleophiles donate electrons, they are by definition Lewis bases.
The terms nucleophile and electrophile are more or less interchangeable with Lewis base and Lewis acid, respectively.