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Related Concept Videos

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...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.0K
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...
2.0K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

3.5K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
3.5K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
3.7K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Formation: Overview01:03

Radical Formation: Overview

2.0K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.0K

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Two Blatter Radicals Face-to-Face: A Constrained Diradical Architecture.

Paulina Bartos1, Dominika Pomikło2, Kadin B Sorenson3

  • 1Faculty of Chemistry, University of Łódź, Tamka 12, 91403 Łódź, Poland.

Journal of the American Chemical Society
|December 20, 2024
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Summary

Researchers developed novel stable diradicals using a peri-naphthalene scaffold. These diradicals exhibit strong through-space interactions and exist as open-shell singlets in solution, with one isomer interconverting between stereoisomers.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Stable organic diradicals are crucial for developing novel magnetic and electronic materials.
  • Designing molecules with controlled through-space interactions is key to tuning radical properties.
  • The peri-naphthalene scaffold offers a unique platform for enforcing specific molecular geometries.

Purpose of the Study:

  • To synthesize and characterize novel diradicals based on a peri-naphthalene scaffold.
  • To investigate the stereoisomerism and electronic properties of these naphthalene-diradicals.
  • To explore the stability and interconversion dynamics of the diradical species.

Main Methods:

  • X-ray diffraction (XRD) for structural determination.
  • Variable-temperature Electron Paramagnetic Resonance (VT-EPR) spectroscopy to study radical behavior.
  • UV-vis spectroscopy, electrochemistry, and kinetic studies for electronic and dynamic characterization.
  • Density Functional Theory (DFT) calculations to understand electronic structure and energetics.

Main Results:

  • Two stereoisomers, anti and syn, of the naphthalene-diradicals were successfully synthesized and characterized.
  • Both isomers exist as open-shell singlets in solution with distinct singlet-triplet energy gaps (ΔES-T = -3.1 and -3.8 kcal mol-1).
  • The anti isomer was resolved into enantiomers and demonstrated a measurable conversion to the syn isomer with a free energy barrier (ΔG‡298 = 23.6(8) kcal mol-1).

Conclusions:

  • The peri-naphthalene scaffold effectively enforces a cofacial arrangement of Blatter radicals, leading to stable diradicals with significant through-space interactions.
  • The study provides a comprehensive understanding of the stereoisomerism, electronic properties, and dynamic behavior of these novel diradicals.
  • These findings open new avenues for the rational design of stable organic radical systems for advanced applications.