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A nitrogen bound to both a good electrofuge and a good nucleofuge is known as a nitrenoid (for its resemblance to a nitrene). [2] Nitrenes lack a full octet of electrons are thus highly electrophilic; nitrenoids exhibit analogous behavior and are often good substrates for electrophilic amination reactions.
A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry. [ 1 ] Nitrogen has five valence electrons and in simple amines it is trivalent , with the two remaining electrons forming a lone pair .
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 ...
Furthermore, mercaptoesters have been employed as H 2 S-equivalents in order to generate the thiophenol from the corresponding aryl halide. [43] Enolates and other similar carbon nucleophiles can also be coupled to produce α-aryl ketones, malonates, nitriles, etc.
The mechanism of S N 2 reaction does not occur due to steric hindrance of the benzene ring. In order to attack the C atom, the nucleophile must approach in line with the C-LG (leaving group) bond from the back, where the benzene ring lies. It follows the general rule for which S N 2 reactions occur only at a tetrahedral carbon atom.
In many nucleophilic reactions, addition to the carbonyl group is very important. In some cases, the C=O double bond is reduced to a C-O single bond when the nucleophile bonds with carbon. For example, in the cyanohydrin reaction a cyanide ion forms a C-C bond by breaking the carbonyl's double bond to form a cyanohydrin.
When used as nitrogen nucleophiles, amino acids can furnish various iminodicarboxylic acid derivatives. High diastereoselectivity is usually observed, and the newly formed stereocenter usually share the same configuration with the starting amino acid. This reaction works well in highly polar solvents (ex. water, ethanol, etc.).
A classic example of NGP is the reaction of a sulfur or nitrogen mustard with a nucleophile, the rate of reaction is much higher for the sulfur mustard and a nucleophile than it would be for a primary or secondary alkyl chloride without a heteroatom. [4] Ph−S−CH 2 −CH 2 −Cl reacts with water 600 times faster than CH 3 −CH 2 −CH 2 ...