A generic name for
carbocations, real or hypothetical, that have at least one important
contributing structure containing a tervalent carbon atom with a vacant p-orbital. (The name implies a protonated
carbene or a substitution derivative thereof.) The term was proposed (and rejected)
as a replacement for the traditional usage of the name
carbonium ion. To avoid ambiguity, the name should not be used as the root for the systematic nomenclature
of carbocations. The corresponding difficulty confused
carbonium ion nomenclature for many years. For example, the term '
ethylcarbonium ion' has at times been used to refer either to
CH3CH2+
(ethyl
cation) or (correctly) to
CH3CH2CH2+
(propyl
cation).
Source:
PAC, 1994, 66, 1077
(Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994))
on page 1092
PAC, 1995, 67, 1307
(Glossary of class names of organic compounds and reactivity intermediates based on
structure (IUPAC Recommendations 1995))
on page 1324
PAC, 1994, 66, 1077
(Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994))
on page 1092
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.
https://doi.org/10.1351/goldbook.
