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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 ...
An alternative quantitative measure is the heat of formation of the Lewis acid-base adduct in a non-coordinating solvent. The ECW model is quantitative model that describes and predicts the strength of Lewis acid base interactions, -ΔH . The model assigned E and C parameters to many Lewis acids and bases.
A Lewis base is often a Brønsted–Lowry base as it can donate a pair of electrons to H +; [11] the proton is a Lewis acid as it can accept a pair of electrons. The conjugate base of a Brønsted–Lowry acid is also a Lewis base as loss of H + from the acid leaves those electrons which were used for the A—H bond as a lone pair on the ...
Synthesis of nucleosides involves the coupling of a nucleophilic, heterocyclic base with an electrophilic sugar. The silyl-Hilbert-Johnson (or Vorbrüggen) reaction, which employs silylated heterocyclic bases and electrophilic sugar derivatives in the presence of a Lewis acid, is the most common method for forming nucleosides in this manner.
According to the original formulation of Lewis, when a neutral base forms a bond with a neutral acid, a condition of electric stress occurs. [7] The acid and the base share the electron pair that formerly belonged to the base. [7] As a result, a high dipole moment is created, which can only be decreased to zero by rearranging the molecules. [7]
The nucleophiles used are typically generated from precursors (pronucleophiles) in situ after their deprotonation with base. [9] These nucleophiles are then subdivided into "hard" and "soft" nucleophiles using a paradigm for describing nucleophiles that largely rests on the pKas of their conjugate acids .
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 +.
An acid-base-nucleophile triad is a common motif for generating a nucleophilic residue for covalent catalysis. The residues form a charge-relay network to polarise and activate the nucleophile, which attacks the substrate, forming a covalent intermediate which is then hydrolysed to release the product and regenerate free