carbonium ion

https://doi.org/10.1351/goldbook.C00839
The term should be used with great care since several incompatible meanings are currently in use. It is not acceptable as the root for systematic nomenclature for carbocation.
  1. In most of the existing literature the term is used in its traditional sense for what is here defined as carbenium ion.
  2. A carbocation, real or hypothetical, that contains at least one five-coordinate carbon atom.
  3. A carbocation, real or hypothetical, whose structure cannot adequately be described by two-electron two-centre bonds only. (The structure may involve carbon atoms with a coordination number greater than five.)
Source:
PAC, 1994, 66, 1077. (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1093 [Terms] [Paper]
See also:
PAC, 1995, 67, 1307. (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1325 [Terms] [Paper]
Citation: 'carbonium ion' 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.C00839 RIS BibTex EndNote
Div. IIIDiv. VIIIPDFTextXMLJSON