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Related Concept Videos

Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...
Radical Formation: Addition00:47

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an unpaired...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

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...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Electron transfer within charge-localized dinitroaromatic radical anions.

João P Telo1, Stephen F Nelsen, Yi Zhao

  • 1Centro de Química Estrutural, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisboa, Portugal. jptelo@ist.utl.pt

The Journal of Physical Chemistry. A
|June 10, 2009
PubMed
Summary

Intramolecular electron-transfer rates were measured for dinitronaphthalene, dinitrotolane, and dimethyl-dinitrobiphenyl radical anions. Solvent dynamics significantly influence these electron-transfer reactions, particularly in polar aprotic solvents.

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Area of Science:

  • Chemical kinetics
  • Electron transfer reactions
  • Spectroscopy

Background:

  • Intramolecular electron transfer is crucial in chemical and biological systems.
  • Understanding solvent effects on reaction rates is essential for predicting chemical behavior.

Purpose of the Study:

  • To estimate rate constants for intramolecular electron transfer in specific radical anions.
  • To investigate the influence of solvent dynamics on these reactions.

Main Methods:

  • Electron spin resonance (ESR) spectroscopy was used to simulate spectra.
  • Rate constants were estimated by analyzing spectral changes at varying temperatures.
  • Kramers-based theory was applied to model the reaction dynamics.

Main Results:

  • Rate constants at 298 K ranged from 0.4-8.0 x 10(9) s(-1) for the studied radical anions.
  • For dinitrotolane and dimethyl-dinitrobiphenyl, rates correlated with solvent relaxation time, indicating solvent control.
  • Solvent effects were prominent for dinitronaphthalene in benzonitrile.

Conclusions:

  • Solvent dynamics play a significant role in controlling intramolecular electron-transfer reactions.
  • Kramers-based theory provides a good fit for describing these solvent-controlled reactions.