Term: electrophile (electrophilic)
https://doi.org/10.1351/goldbook.E02020

Definition:
An electrophile (or electrophilic reagent) is a reagent that forms a bond to its reaction partner (the nucleophile) by accepting both bonding electrons from that reaction partner. An 'electrophilic substitution reaction' is a heterolytic reaction in which the reagent supplying the entering group acts as an electrophile. For example: E02020.png Electrophilic reagents are Lewis acids. 'Electrophilic catalysis' is catalysis by Lewis acids. The term 'electrophilic' is also used to designate the apparent polar character of certain radicals as inferred from their higher relative reactivities with reaction sites of higher electron density.

Related Terms:
1) electrophilicity (http://doi.org/10.1351/goldbook.E02021).
2) reagent (http://doi.org/10.1351/goldbook.R05190).
3) entering group (http://doi.org/10.1351/goldbook.E02130).
4) catalysis (http://doi.org/10.1351/goldbook.C00874).
5) electron density (http://doi.org/10.1351/goldbook.E01986).
6) nucleophile (http://doi.org/10.1351/goldbook.N04249).
7) substitution reaction (http://doi.org/10.1351/goldbook.S06078).
8) heterolytic (http://doi.org/10.1351/goldbook.H02809).
9) lewis acids (http://doi.org/10.1351/goldbook.L03508).
10) radicals (http://doi.org/10.1351/goldbook.R05066).

Image: Not defined (https://goldbook.iupac.org/img/inline/E02020.png) 

Source: PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1111 (https://doi.org/10.1351/pac199466051077)

Citation: 'electrophile (electrophilic)' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.E02020

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