Electrophile vs Nucleophile

An electrophile is a species which is electron deficient which can accept a lone pair of electrons. This includes positively charged cations/cationic species such as H⁺ or the acyl cation (see Friedal-Crafts acylation) and neutral species which have vacant orbitals free to accept a lone pair of electrons such as boron.

A nucleophile is a species which is electron rich which can donate a lone pair of electrons. This includes negatively charged anions/anionic species such as F⁻ or the hydroxide anion (⁻OH) and neutral species which are able to donate a lone pair of electrons such as amines.

These two terms are used readily along side each other as nucleophiles which are electron rich attack (or react with) electron electrophiles. These terms are also used to describe types of reactions:

  • nucleophilic addition-elimination
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