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Nucleophile information


A hydroxide ion acting as a nucleophile in an SN2 reaction, converting a haloalkane into an alcohol

In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases.

Nucleophilic describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. The difference between the two is, that basicity is a thermodynamic property (i.e. relates to an equilibrium state), but nucleophilicity is a kinetic property, which relates to rates of certain chemical reactions.[1]

  1. ^ Nucleophilicity—Periodic Trends and Connection to Basicity. Einar Uggerud. https://doi.org/10.1002/chem.200500639

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Nucleophile

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can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. Nucleophilic describes the affinity of a nucleophile to bond with...

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SN2 reaction

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mechanism that is common in organic chemistry. In the SN2 reaction, a strong nucleophile forms a new bond to an sp3-hybridised carbon atom via a backside attack...

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Nucleophilic substitution

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chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule...

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SN1 reaction

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and zero-order dependence on the nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the...

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Catalytic triad

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amidases, esterases, acylases, lipases and β-lactamases). An acid-base-nucleophile triad is a common motif for generating a nucleophilic residue for covalent...

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Nucleophilic addition

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chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions...

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Michael addition reaction

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addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce...

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Chemical reaction

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pair from the nucleophile attacks the substrate forming a new bond, while the leaving group departs with an electron pair. The nucleophile may be electrically...

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Hydroxide

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usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate...

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Hydrolysis

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substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water...

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Mitsunobu reaction

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nucleophile displaces it. A common side-product is produced when the azodicarboxylate displaces the leaving group instead of the desired nucleophile....

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Enamine

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second carbon atom. Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following...

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Solvolysis

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type of nucleophilic substitution (SN1/SN2) or elimination where the nucleophile is a solvent molecule. Characteristic of SN1 reactions, solvolysis of...

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Nucleophilic acyl substitution

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class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile – such as an alcohol, amine, or enolate...

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Nucleophilic aromatic substitution

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(SNAr) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring...

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Aldehyde

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From the biological perspective, the key reactions involve addition of nucleophiles to the formyl carbon in the formation of imines (oxidative deamination)...

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Electrophile

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chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons...

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Substitution reaction

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nucleophilic substitution is a fundamental class of reactions in which a nucleophile selectively bonds with or attacks the positive or partially positive...

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Protease

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to make a nucleophile is by a catalytic triad, where a histidine residue is used to activate serine, cysteine, or threonine as a nucleophile. This is not...

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Electrophilic substitution

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similar to nucleophilic aliphatic substitution where the reactant is a nucleophile rather than an electrophile. The four possible electrophilic aliphatic...

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Potassium hydroxide

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Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a...

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Walden inversion

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inside-out in a gale. In the Walden inversion, the backside attack by the nucleophile in an SN2 reaction gives rise to a product whose configuration is opposite...

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Diazo

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In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic...

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