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tert-Butoxide, on the other hand, is a strong base, but a poor nucleophile, because of its three methyl groups hindering its approach to the carbon. Nucleophile strength is also affected by charge and electronegativity : nucleophilicity increases with increasing negative charge and decreasing electronegativity.
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 ...
The case for S N 2 reactions is quite different, as the lack of solvation on the nucleophile increases the rate of an S N 2 reaction. In either case (S N 1 or S N 2), the ability to either stabilize the transition state (S N 1) or destabilize the reactant starting material (S N 2) acts to decrease the ΔG ‡ activation and thereby increase the ...
As a reagent in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen. [5] Lewis acids also attach to the same nitrogen. [6] These properties recommend DBU for use as a catalyst, for example as a curing agent for epoxy resins and polyurethane.
An application of HSAB theory is the so-called Kornblum's rule (after Nathan Kornblum) which states that in reactions with ambident nucleophiles (nucleophiles that can attack from two or more places), the more electronegative atom reacts when the reaction mechanism is S N 1 and the less electronegative one in a S N 2 reaction.
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.
with regards to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids. [ 4 ] with regards to nucleophilic substitution reactions , electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles.
The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines. [3] Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control ).