Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene

Symmetry

Tohru Nishinaga¹  Takeshi Ohmae¹ 

[1] Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan

关键词: antiaromaticity;    cyclooctatetraene;    NMR chemical shifts;    quantum chemical calculations;    ring current;   

DOI  :  10.3390/sym2010076

来源: mdpi

【 摘 要 】

Cyclooctatetraene (COT), the first 4nπ-electron system to be studied, adopts an inherently nonplanar tub-shaped geometry of D_2d symmetry with alternating single and double bonds, and hence behaves as a nonaromatic polyene rather than an antiaromatic compound. Recently, however, considerable 8π-antiaromatic paratropicity has been shown to be generated in planar COT rings even with the bond alternated D_4h structure. In this review, we highlight recent theoretical and experimental studies on the antiaromaticity of hypothetical and actual planar COT. In addition, theoretically predicted triplet aromaticity and stacked aromaticity of planar COT are also briefly described.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.