IUPAC > Gold Book > alphabetical index > N > nucleophile (nucleophilic)


nucleophile (nucleophilic)

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.
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1146
Interactive Link Maps
First LevelSecond LevelThird Level
Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.N04249.
Original PDF version: http://www.iupac.org/goldbook/N04249.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
Current PDF version | Version for print | History of this term