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

Eric R. Abbey, Lev N. Zakharov and Shih-Yuan Liu
Department of Chemistry, University of Oregon, Eugene, Oregon 97403
J. Am. Chem. Soc., 2008, 130 (23), pp 7250–7252
DOI: 10.1021/ja8024966
Publication Date (Web): May 14, 2008
Copyright © 2008 American Chemical Society

Abstract

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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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History

  • Published In Issue June 11, 2008
  • Article ASAPMay 14, 2008
  • Received: April 10, 2008

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