Structural and Aromaticity Control of [34]Octaphyrin(1.1.1.0.1.1.1.0) by Protonation and Deprotonation,Asian Journal of Organic Chemistry

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Structural and Aromaticity Control of [34]Octaphyrin(1.1.1.0.1.1.1.0) by Protonation and Deprotonation
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-04-18 , DOI: 10.1002/ajoc.201700144
Koji Naoda ₁ , Atsuhiro Osuka ₁

Affiliation

The structural and aromaticity control of hexakis(pentafluorophenyl) [34]octaphyrin(1.1.1.0.1.1.1.0) 1 was examined by protonation and deprotonation. Protonation of 1 with methanesulfonic acid (MSA) induced a structural change from a figure‐eight to a rectangular shape, accompanied by an aromaticity change from nonaromatic to strong Hückel aromatic. Deprotonation of 1 with tetrabutylammonium difluorotriphenylsilicate (TBAT) or fluoride (TBAF) produced a mono‐deprotonated species with a similar figure‐eight conformation and nonaromaticity.

中文翻译：

通过质子化和去质子化控制[34]八氢卟啉（1.1.1.0.1.1.1.0）的结构和芳香性

通过质子化和去质子化检查了六（五氟苯基）[34]八卟啉（1.1.1.0.1.1.1.0）1的结构和芳香性控制。甲磺酸（MSA）使1的质子化导致结构从八字形变为矩形，并伴随着芳香性从非芳香族到强Hückel芳香族的变化。去质子化1用四丁基difluorotriphenylsilicate（TBAT）或氟化铵（TBAF）中产生具有类似的八字形构象和nonaromaticity单去质子化物种。

更新日期：2017-04-18

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