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Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

Enolate Mechanism Conventions

Enolate Mechanism Conventions

When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as...

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly,...

Carboxylic Acid Derivatives: Overview

Carboxylic Acid Derivatives: Overview

Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:

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Updated: Apr 16, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Gold carbene or carbenoid: is there a difference?

Yahui Wang¹, Michael E Muratore, Antonio M Echavarren

¹Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 20, 2015

Summary

This review recommends using "gold carbene" for gold carbene-like intermediates, unifying terminology. Gold carbenes, despite similarities to Fischer carbenes, exhibit unique reactivity due to weak π-back-donation.

Keywords:

Fischer carbenes carbenes carbenoids carbocations gold

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Published on: March 12, 2015

Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Recent advancements in understanding gold carbene structures.
Existing definitions of metal carbenes and carbenoids lack specificity for gold complexes.
Need for standardized nomenclature in gold carbene chemistry.

Purpose of the Study:

To propose a consistent and accurate term for gold carbene-like intermediates.
To clarify the classification of gold carbenes within broader metal carbene families.
To highlight the unique characteristics of gold carbenes.

Main Methods:

Comprehensive literature review of gold carbene structures and reactivity.
Analysis of resonance structures and electronic properties.
Comparison with established metal carbene and carbenoid classifications.

Main Results:

Recommendation to use the term "gold carbene" for intermediates where carbene or carbocation resonance dominates.
Identification of weak metal-to-carbene π-back-donation as a key feature.
Strong electrophilic reactivity characteristic of gold carbenes.

Conclusions:

"Gold carbene" provides a unified descriptor for these reactive intermediates.
Gold carbenes share characteristics with Fischer carbenes but possess distinct properties.
Understanding these unique properties is crucial for their application in catalysis.