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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

3.0K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
3.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.0K
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

3.6K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
3.6K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.6K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
5.6K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

10.3K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
10.3K

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Gas-Phase Reactivity of Quinoline-Based Singlet Oxenium Cations.

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The Journal of Organic Chemistry
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Gas-phase quinolyloxenium cations exhibit closed-shell singlet ground states, demonstrating strong electrophilic reactivity. These cations readily react with nucleophiles and undergo hydride abstraction, revealing insights into their chemical behavior.

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Area of Science:

  • Physical Organic Chemistry
  • Mass Spectrometry
  • Computational Chemistry

Background:

  • Quinolyloxenium cations are reactive intermediates whose gas-phase chemistry remains underexplored.
  • Understanding the electronic structure and reactivity of such cations is crucial for various chemical applications.

Purpose of the Study:

  • To generate and characterize isomeric quinolyloxenium cations in the gas phase.
  • To investigate the reactivity of these cations with various nucleophiles and substrates.
  • To elucidate the electronic ground state and structural properties of quinolyloxenium cations.

Main Methods:

  • Generation of quinolyloxenium cations using an ion trap mass spectrometer.
  • Structure elucidation via collision-activated dissociation (CAD) experiments on model compounds.
  • Computational studies employing CASPT2/CASSCF(16,14)/cc-pVTZ//CASSCF(16,14)/cc-pVTZ calculations.

Main Results:

  • Lack of radical reactions indicates closed-shell singlet electronic ground states for the cations.
  • Calculations confirm singlet ground states are significantly lower in energy than excited states.
  • Cations display strong electrophilicity, reacting exothermically with nucleophiles (e.g., dimethyl sulfide) and undergoing hydride abstraction with cyclohexane.

Conclusions:

  • Quinolyloxenium cations possess stable singlet ground states and exhibit pronounced electrophilic character.
  • Reactions with nucleophiles occur preferentially at electron-deficient carbon atoms in the benzene ring.
  • Hydride abstraction by the oxygen atom is a key reaction pathway, highlighting the cation's unique reactivity.