Resonance stabilization energy of 1,2-azaborines: a quantitative experimental study by reaction calorimetry

J Am Chem Soc. 2010 Dec 29;132(51):18048-50. doi: 10.1021/ja109596m. Epub 2010 Dec 8.

Abstract

Aromatic and single-olefin six-membered BN heterocycles were synthesized, and the heats of hydrogenation were measured calorimetrically. A comparison of the hydrogenation enthalpies of these compounds revealed that 1,2-azaborines have a resonance stabilization energy of 16.6 ± 1.3 kcal/mol, in good agreement with calculated values.