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One-Electron Boron-Carbon Triel Bonding.

Paula Castro Castro¹, Wei-Chun Liu¹, François P Gabbaï¹

¹Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, United States of America.

Journal of the American Chemical Society

|September 17, 2025

Summary

This summary is machine-generated.

Researchers explored one-electron bonding between boron and carbon in a naphthalene system. They found the B-C bond in the radical species is best described as a noncovalent triel bond, not a covalent sigma bond.

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Area of Science:

Organic Chemistry
Computational Chemistry
Spectroscopy

Background:

Investigating novel bonding interactions is crucial for advancing chemical understanding.
The formation of one-electron bonds, particularly between different elements, remains an area of active research.

Purpose of the Study:

To explore the possibility of heteronuclear one-electron sigma bonding between boron and carbon.
To characterize a naphthalene-based platform with adjacent carbenium and boryl units.

Main Methods:

Synthesis of a naphthalene-based cationic platform.
Electrochemical reduction to generate radical and borate species.
Structural, spectroscopic (including EPR), and computational investigations.

Main Results:

A cationic platform ([5]+) with a B-C distance of 2.994(4) Å was prepared.
Reduction to a radical ([5]•) shortened the B-C distance to 2.874(3) Å, indicating incipient bonding.
Further reduction to a borate ([5]-) resulted in a long, polar covalent B-C bond (1.793(8) Å).
The B-C bond in [5]• was characterized as a noncovalent triel bond, not a covalent sigma bond.

Conclusions:

The study provides insights into the nature of the B-C bond in the radical species.
The findings suggest that the observed interaction is better classified as a triel bond.
This work contributes to the understanding of unusual bonding motifs in chemistry.