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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.
Because they form a strong electrophile when treated with Lewis acids, acyl halides are commonly used as acylating agents. For example, Friedel–Crafts acylation uses acetyl chloride (CH 3 COCl) as the agent and aluminum chloride (AlCl 3) as a catalyst to add an acetyl group to benzene: [2]
The most common Lewis bases are anions. The strength of Lewis basicity correlates with the pK a of the parent acid: acids with high pK a 's give good Lewis bases. As usual, a weaker acid has a stronger conjugate base. Examples of Lewis bases based on the general definition of electron pair donor include:
Like all Grignard reagents, propylmagnesium bromide is a strong electrophile, sensitive to both water and air. The propylmagnesium halides are the simplest Grignard reagents to exhibit isomerism . Isopropylmagnesium chloride is the primary synthetic equivalent of the isopropyl group .
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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.
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This makes the molecule an electrophile, and the carbon atom the electrophilic center; this atom is the primary target for the nucleophile. Chemists have developed a geometric system to describe the approach of the nucleophile to the electrophilic center, using two angles, the Bürgi–Dunitz and the Flippin–Lodge angles after scientists that ...