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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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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...
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The perchlorotriphenylmethyl (PTM) radical.

Judith Guasch1, Xavier Fontrodona, Imma Ratera

  • 1Institut de Ciència de Materials de Barcelona (CSIC)/CIBER-BBN, Campus de Bellaterra, 08193 Cerdanyola del Vallès, Barcelona, Spain.

Acta Crystallographica. Section C, Crystal Structure Communications
|March 6, 2013
PubMed
Summary

Researchers successfully prepared pure perchlorotriphenylmethyl (PTM) radical crystals for X-ray diffraction. The study reveals a unique propeller conformation and layered supramolecular structure stabilized by chlorine interactions, enhancing PTM

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Perchlorotriphenylmethyl (PTM) radical derivatives are well-studied, but obtaining pure, unsubstituted PTM crystals for structural analysis has been difficult.
  • Previous studies on unsubstituted PTM crystal structure were limited, relying on clathrate formation or powder diffraction data.

Purpose of the Study:

  • To prepare pure perchlorotriphenylmethyl (PTM) radical crystals suitable for single-crystal X-ray diffraction.
  • To resolve and analyze the crystal structure of the unsubstituted PTM radical.

Main Methods:

  • Single-crystal X-ray diffraction.
  • Crystal preparation and resolution techniques.

Main Results:

  • Successfully obtained PTM crystals for single-crystal X-ray diffraction.
  • Determined the crystal structure exhibiting monoclinic symmetry (C2/c).
  • Revealed a non-symmetric molecular propeller conformation (D3 symmetry) due to steric hindrance from ortho-chlorine atoms, contributing to PTM's stability.
  • Identified short Cl...Cl intermolecular interactions forming a layered supramolecular structure with head-to-tail molecular arrangement along the c-axis.

Conclusions:

  • The study provides the first high-resolution single-crystal structure of the unsubstituted PTM radical.
  • The propeller conformation and intermolecular chlorine interactions are key features influencing the radical's stability and packing.
  • This work advances the understanding of PTM radical's solid-state properties and supramolecular assembly.