Crystal Clear Structural Evidence for Electron Delocalization in 1,2-Dihydro-1,2-azaborines

The first examples of “pre-aromatic” 1,2-dihydro-1,2-azaborine heterocycles have been structurally characterized, enabling the direct comparison of delocalized bonds of 1,2-dihydro-1,2-azaborines to their corresponding formal double and single bonds in nonaromatic systems. The crystallographic data...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-06, Vol.130 (23), p.7250-7252
Main Authors: Abbey, Eric R, Zakharov, Lev N, Liu, Shih-Yuan
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Boron Compounds - chemistry
Electrons
Heterocyclic Compounds - chemistry
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Summary:The first examples of “pre-aromatic” 1,2-dihydro-1,2-azaborine heterocycles have been structurally characterized, enabling the direct comparison of delocalized bonds of 1,2-dihydro-1,2-azaborines to their corresponding formal double and single bonds in nonaromatic systems. The crystallographic data provide an unprecedented look into the structural changes that occur in six-membered BN-heterocycles on their road to aromaticity, and they establish with little ambiguity that 1,2-dihydro-1,2-azaborines possess delocalized structures consistent with aromaticity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja8024966