Breton Gary W, Martin Kenneth L
Department of Chemistry, Berry College, P.O. Box 495016, Mount Berry, Georgia 30149, USA.
J Org Chem. 2002 Sep 20;67(19):6699-704. doi: 10.1021/jo026082m.
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.
对1,2 - 二氢二氮杂环丁烷环系的芳香性进行了全面的实验和计算研究。报道了1,2 - 二氢二氮杂环丁烷6的X射线晶体结构，并描述了化合物6的烯烃样反应活性。该化合物的结构和反应活性表明6不具有芳香性。对6及相关化合物进行的计算结果证实了这一结论，这些计算包括用于测试芳香稳定化的同系反应、核独立化学位移（NICS）计算和自然键轨道（NBO）计算。得出结论，化合物6以及一般的1,2 - 二氢二氮杂环丁烷是具有张力的杂环，没有芳香稳定化的迹象。
