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Nevertheless, one can generally examine acid dissociation constants to qualitatively predict or rationalize rate or reactivity trends relating to variation of the leaving group. Consistent with this picture, strong bases such as OH −, OR 2 and NR − 2 tend to make poor leaving groups, due their inability to stabilize a negative charge.
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 ...
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.
The electron pair (:) from the nucleophile (Nuc) attacks the substrate (R−LG) and bonds with it. Simultaneously, the leaving group (LG) departs with an electron pair. The principal product in this case is R−Nuc. The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged.
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.
where k and k 0 are the rate constants for a nucleophile and a standard (H 2 O). H is a measure of the basicity of the nucleophile relative to protons, as defined by the equation: = + where the pK a is that of the conjugate acid of the nucleophile and the constant 1.74 is the correction for the pK a of H 3 O +.
Gilbert N. Lewis introduced the concepts of both the electron pair and the covalent bond in a landmark paper he published in 1916. [1] [2] MO diagrams depicting covalent (left) and polar covalent (right) bonding in a diatomic molecule. In both cases a bond is created by the formation of an electron pair.
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.