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  2. n-Butyllithium - Wikipedia

    en.wikipedia.org/wiki/N-Butyllithium

    Butyllithium is a strong base (pK b ≈ -36), but it is also a powerful nucleophile and reductant, depending on the other reactants. Furthermore, in addition to being a strong nucleophile, n -BuLi binds to aprotic Lewis bases, such as ethers and tertiary amines , which partially disaggregate the clusters by binding to the lithium centers.

  3. Phenolates - Wikipedia

    en.wikipedia.org/wiki/Phenolates

    Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions. [2] At pH = 10, phenol and phenolate are in approximately 1:1 proportions. The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines. [3]

  4. SN2 reaction - Wikipedia

    en.wikipedia.org/wiki/SN2_reaction

    For example, OH − is a better nucleophile than water, and I − is a better nucleophile than Br − (in polar protic solvents). In a polar aprotic solvent, nucleophilicity increases up a column of the periodic table as there is no hydrogen bonding between the solvent and nucleophile; in this case nucleophilicity mirrors basicity.

  5. Solvent effects - Wikipedia

    en.wikipedia.org/wiki/Solvent_effects

    The rate equation for S N 2 reactions are bimolecular being first order in Nucleophile and first order in Reagent. The determining factor when both S N 2 and S N 1 reaction mechanisms are viable is the strength of the Nucleophile. Nuclephilicity and basicity are linked and the more nucleophilic a molecule becomes the greater said nucleophile's ...

  6. Nucleophile - Wikipedia

    en.wikipedia.org/wiki/Nucleophile

    A hydroxide ion acting as a nucleophile in an S N 2 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 ...

  7. Methanethiol - Wikipedia

    en.wikipedia.org/wiki/Methanethiol

    The resulting thiolate anion is a strong nucleophile. It can be oxidized to dimethyl disulfide: 2CH 3 SH + [O] → CH 3 SSCH 3 + H 2 O. Further oxidation takes the disulfide to two molecules of methanesulfonic acid, which is odorless. Bleach deodorizes methanethiol in this way.

  8. tert-Butyllithium - Wikipedia

    en.wikipedia.org/wiki/Tert-Butyllithium

    tert-butyllithium is a pyrophoric substance, meaning that it spontaneously ignites on exposure to air. Air-free techniques are important so as to prevent this compound from reacting violently with oxygen and moisture: t-BuLi + O 2 → t-BuOOLi t-BuLi + H 2 O → t-BuH + LiOH. The solvents used in common commercial preparations are themselves ...

  9. Protic solvent - Wikipedia

    en.wikipedia.org/wiki/Protic_solvent

    In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group −OH), a nitrogen (as in an amine group −NH 2 or −NH−), or fluoride (as in hydrogen fluoride).