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In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. [1] Because electrophiles accept electrons, they are Lewis acids . [ 2 ] Most electrophiles are positively charged , have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.
For instance, using methyl iodide as the reference electrophile, Ph 3 Sn – is about 10000 times more nucleophilic than I –, while the Co(I) form of vitamin B 12 (vitamin B 12s) is about 10 7 times more nucleophilic. [14] Other supernucleophilic metal centers include low oxidation state carbonyl metalate anions (e.g., CpFe(CO) 2 –). [15]
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.
In chemistry, a nucleophilic substitution (S N) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the ...
Electrophiles are involved in electrophilic substitution reactions, particularly in electrophilic aromatic substitutions. In this example, the benzene ring's electron resonance structure is attacked by an electrophile E +. The resonating bond is broken and a carbocation resonating structure results.
With nitrile electrophiles, nucleophilic addition take place by: [1] hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction.
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According to findings, electrophilic alkylations at free CN − occur preferentially at carbon, regardless of whether the S N 1 or S N 2 mechanism is involved and whether hard or soft electrophiles are employed. Preferred N attack, as postulated for hard electrophiles by the HSAB principle, could not be observed with any alkylating agent.