Are 1,2-dihydrodiazetes aromatic? An experimental and computational investigation.
A thorough experimental and computational investigation of the aromaticity of the 1,2-dihydrodiazete ring system was carried out. The X-ray crystal structure of 1,2-dihydrodiazete 6 is reported, and the alkene-like reactivity of compound 6 is described. The compound's structure and reactivity suggest that 6 is not aromatic. This conclusion is corroborated by computational results on 6 and related compounds including homodesmotic reactions to test for aromatic stabilization, NICS calculations, and NBO calculations. Compound 6, and 1,2-dihydrodiazetes in general, are concluded to be strained heterocycles with no indication for aromatic stabilization.
Breton
Gary W
GW
Department of Chemistry, Berry College, P.O. Box 495016, Mount Berry, Georgia 30149, USA. gbreton@berry.edu
Martin
Kenneth L
KL