Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene

doi:10.3390/sym2010076

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Symmetry 2010, 2(1), 76-97; doi:10.3390/sym2010076

Review

Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene

Tohru Nishinaga * , Takeshi Ohmae and Masahiko Iyoda

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

* Author to whom correspondence should be addressed.

Received: 29 December 2009; in revised form: 23 January 2010 / Accepted: 4 February 2010 / Published: 5 February 2010

(This article belongs to the Special Issue Aromaticity and Molecular Symmetry)

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Abstract: 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_4hstructure. 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.

Keywords: antiaromaticity; cyclooctatetraene; NMR chemical shifts; quantum chemical calculations; ring current

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MDPI and ACS Style

Nishinaga, T.; Ohmae, T.; Iyoda, M. Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene. Symmetry 2010, 2, 76-97.

AMA Style

Nishinaga T., Ohmae T., Iyoda M. Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene. Symmetry. 2010; 2(1):76-97.

Chicago/Turabian Style

Nishinaga, Tohru; Ohmae, Takeshi; Iyoda, Masahiko. 2010. "Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene." Symmetry 2, no. 1: 76-97.

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