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Related Concept Videos

Carbocations02:10

Carbocations

11.1K
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...
11.1K
Electrophiles02:28

Electrophiles

10.6K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
10.6K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
1.9K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.0K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.0K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

2.5K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
2.5K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

3.2K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.2K

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Related Experiment Video

Updated: Jun 22, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Superelectrophilic Nonclassical Carbocations.

Jacob C Hood1, Pierre Esteves2, Milan Gembicky3

  • 1Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, United States.

The Journal of Organic Chemistry
|July 2, 2024
PubMed
Summary
This summary is machine-generated.

Researchers explored highly charged norbornyl cations, revealing their reactivity with arenes. Computational studies indicate increased positive charge enhances nonclassical bonding in these superelectrophilic species.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • 2-Norbornyl cations are key intermediates in organic reactions.
  • Understanding the behavior of highly charged carbocations is crucial for reaction mechanism elucidation.

Purpose of the Study:

  • To investigate the chemistry of dicationic and tricationic 2-norbornyl cations.
  • To explore the reactivity and structural properties of superelectrophilic species.

Main Methods:

  • Synthesis of N-heterocyclic functionalized norborneol substrates.
  • Ionization of substrates in superacid to generate highly charged cations.
  • Reaction of cations with arene nucleophiles.
  • Density functional theory (DFT) computational studies.

Main Results:

  • Superelectrophilic dicationic and tricationic 2-norbornyl cations were successfully generated.
  • These cations reacted with arene nucleophiles with high yields and stereoselectivity.
  • DFT calculations indicated that increased positive charge enhances nonclassical (3-center-2-electron) bonding.

Conclusions:

  • Highly charged 2-norbornyl cations exhibit unique reactivity patterns.
  • The degree of nonclassical bonding is influenced by the overall positive charge.
  • This study provides insights into the fundamental chemistry of polycationic species.