04249
nucleophile
IUPAC Gold Book - nucleophile
10.1351/goldbook.N04249
N04249
current
synonym: nucleophilic
-
1
A nucleophile (or nucleophilic reagent) is a reagent that forms a bond to its reaction partner (the electrophile) by donating both bonding electrons. A 'nucleophilic substitution reaction' is a heterolytic reaction in which the reagent supplying the entering group acts as a nucleophile. For example: The term 'nucleophilic' is also used to designate the apparent polar character of certain radicals, as inferred from their higher relative reactivity with reaction sites of lower electron density. Nucleophilic reagents are Lewis bases.
-
Lewis bases
https://goldbook.iupac.org/terms/view/L03511
-
electron density
https://goldbook.iupac.org/terms/view/E01986
-
electrophile
https://goldbook.iupac.org/terms/view/E02020
-
entering group
https://goldbook.iupac.org/terms/view/E02130
-
heterolytic
https://goldbook.iupac.org/terms/view/H02809
-
radicals
https://goldbook.iupac.org/terms/view/R05066
-
reagent
https://goldbook.iupac.org/terms/view/R05190
-
substitution reaction
https://goldbook.iupac.org/terms/view/S06078
- PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1146 (https://doi.org/10.1351/pac199466051077)
https://goldbook.iupac.org/terms/view/N04249/html
https://goldbook.iupac.org/terms/view/N04249/json
https://goldbook.iupac.org/terms/view/N04249/plain
Citation: 'nucleophile' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. 10.1351/goldbook.N04249
The IUPAC Gold Book is licensed under Creative Commons Attribution-ShareAlike CC BY-SA 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) for individual terms.
If you are interested in licensing the Gold Book for commercial use, please contact the IUPAC Executive Director at executivedirector@iupac.org .
The International Union of Pure and Applied Chemistry (IUPAC) is continuously reviewing and, where needed, updating terms in the Compendium of Chemical Terminology (the IUPAC Gold Book). Users of these terms are encouraged to include the version of a term with its use and to check regularly for updates to term definitions that you are using.
2026-06-28T07:19:02+00:00