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Borepin Rings as "Sigma-Free" Reporters of Aromaticity within Polycyclic Aromatic Scaffolds.
Reid E Messersmith1, John D Tovar1,2
1Department of Chemistry , Johns Hopkins University , 3400 North Charles Street , Baltimore , Maryland 21218 , United States of America.
The Journal of Physical Chemistry. A
|January 9, 2019
Summary
This study explores aromaticity in fused polycyclic aromatic compounds using borepin rings. Findings reveal the borepin ring
Area of Science:
- Organic Chemistry
- Computational Chemistry
Background:
- Defining and measuring aromaticity in fused polycyclic aromatic compounds (PACs) is challenging.
- Traditional methods include experimental (NMR, thermochemistry) and computational (NICS, HOMA) analyses.
Purpose of the Study:
- To investigate the influence of ring fusion on aromaticity in borepin-containing PACs.
- To analyze the structural and magnetic aromatic character of these extended molecules.
Main Methods:
- Joint experimental and computational analysis.
- Utilizing borepin rings as magnetic aromaticity reporters.
Main Results:
- The borepin ring in fused PACs exhibits unique properties.
- It shows limited sigma-contribution to aromaticity.
- A wide range of structural and magnetic aromatic character was observed.
Conclusions:
- The borepin ring is a distinct structural motif for assessing aromaticity in complex PACs.
- Ring fusion significantly impacts the aromatic character of borepin-containing systems.