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2008•Journal of the American Chemical SocietyRequires access

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

Eric R. Abbey, Lev N. Zakharov, Shih‐Yuan Liu

Open publisher page 230 citations

Abstract

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.

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What this paper is about

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.

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Available abstract

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.

Key concepts: Delocalized electron, Chemistry, Aromaticity, Electron delocalization, Crystallography, Crystal (programming language), Crystal structure, Ambiguity

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