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A Phosphine-Coordinated Boron-Centered Gomberg-Type Radical.

Amos J Rosenthal¹, Marc Devillard¹, Karinne Miqueu²

¹Laboratoire Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier/CNRS UMR 5069, 118 Route de Narbonne, 31062 Toulouse Cedex 09 (France) http://lhfa.cnrs.fr/index.php/equipes/lbpb.

Angewandte Chemie (International Ed. in English)

|June 30, 2015

Summary

This summary is machine-generated.

A novel P-coordinated boryl radical was synthesized and characterized. This persistent radical undergoes dimerization, forming a stable quinoid-type structure, revealing unique P-B interactions.

Keywords:

EPR spectroscopy boron cyclic voltammetry phosphorus radicals

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Area of Science:

Organometallic Chemistry
Radical Chemistry
Boron Chemistry

Background:

Boryl radicals are reactive intermediates with limited stability.
Understanding the electronic structure and reactivity of boryl radicals is crucial for developing new synthetic methodologies.

Purpose of the Study:

To synthesize and characterize a novel P-coordinated boryl radical.
To investigate the electronic properties and intermolecular interactions of the boryl radical.
To explore the reactivity and dimerization behavior of the boryl radical.

Main Methods:

Electrochemical and chemical reduction of borenium salts and bromoboranes.
Electron paramagnetic resonance (EPR) spectroscopy for radical characterization.
Density Functional Theory (DFT) calculations for electronic structure analysis.
Single-crystal X-ray diffraction for dimer structure determination.

Main Results:

Successful synthesis of the P-coordinated boryl radical [Ph2P(naphthyl)BMes]˙.
EPR and DFT calculations revealed significant spin density on boron (60-70%) and strong P-B interactions.
The radical demonstrated persistence in solution and underwent Gomberg-type dimerization.
The resulting quinoid-type dimer was structurally characterized by X-ray diffraction.

Conclusions:

The P-coordinated boryl radical exhibits unique electronic properties and stability due to strong P-B interactions.
The radical's propensity for dimerization highlights its potential in forming novel molecular architectures.
This study provides fundamental insights into the chemistry of persistent boryl radicals.