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carbenium ion

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
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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.C00812.
Original PDF version: http://www.iupac.org/goldbook/C00812.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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