Title: stereospecificity
Long Title: IUPAC Gold Book - stereospecificity
DOI: 10.1351/goldbook.S05994
Status: current

Definition
A reaction is termed stereospecific if starting materials differing only in their configuration are converted into stereoisomeric products. According to this definition, a stereospecific process is necessarily stereoselectivity but not all stereoselective processes are stereospecific. Stereospecificity may be total (100%) or partial. The term is also applied to situations where reaction can be performed with only one stereoisomer. For example, the exclusive formation of trans-1,2-dibromocyclohexane upon bromination of cyclohexene is a stereospecific process, although the analogous reaction with (E)-cyclohexene has not been performed.The term has also been applied to describe a reaction of very high stereoselectivity, but this usage is unnecessary and is discouraged.

Related Terms
- configuration: https://goldbook.iupac.org/terms/view/C01249
- stereoselectivity: https://goldbook.iupac.org/terms/view/S05991
- trans: https://goldbook.iupac.org/terms/view/C01092

Source
- PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1167 (https://doi.org/10.1351/pac199466051077)

Related Reference
- PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2219 (https://doi.org/10.1351/pac199668122193)

Other Outputs
- html: https://goldbook.iupac.org/terms/view/S05994/html
- json: https://goldbook.iupac.org/terms/view/S05994/json
- xml: https://goldbook.iupac.org/terms/view/S05994/xml

Citation: Citation: 'stereospecificity' 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.S05994
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Accessed: 2026-06-28T20:56:51+00:00