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Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula NaNH 2.It is a salt composed of the sodium cation and the azanide anion.
However, it has the disadvantage to be prone to trigger unexpected and undesirable side reactions that can jeopardize the experimental results. Indeed, the azide anion is a nucleophile and a redox-active species. Being prone to disproportionation, it can behave both as an oxidizing and as a reducing agent. Therefore, it is susceptible to ...
Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions. Typical non-nucleophilic bases are bulky, such that protons can attach to the basic center but alkylation and complexation is inhibited.
With carbon nucleophiles such as 1,3-dicarbonyl compounds the reaction has been demonstrated as a method for the asymmetric synthesis of chiral molecules. [9] First reported in 2005, the organocatalyst (in a dual role with that of a phase transfer catalyst) is derived from cinchonidine (benzylated at N and O).
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 mechanism above, loss of the hydride ion followed by abstraction of a proton, is supported by the fact that the nucleophile needs at least one hydrogen atom for the reaction to proceed. Another competing pathway could be the elimination of hydride by sodium to form sodium hydride.
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Other driving forces including the tighter transition state [10] and higher polarizability of α-nucleophiles, involvement of intramolecular catalysis also plays a role. Another in silico study did find a correlation between the alpha effect and the so-called deformation energy, which is the electronic energy required to bring the two reactants ...