Captodative Substituent Effects and the Chromophoric System of Indigo

Captodative Substituent Effects and the Chromophoric System of Indigo
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靛蓝的捕获取代基效应和发色系统

DOI:
10.1002/anie.198009081
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发表时间:
1980
期刊:
影响因子:
--
通讯作者:
M. Klessinger
M. Klessinger
中科院分区:
--
文献类型:
--
作者:
M. Klessinger

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本文讨论了Viehe等最近讨论的自由基稳定化原理。[1]不仅在自由基和亲自由基的合成方面具有重要意义,而且被证明是理解有机化合物许多性质的基本模型。这可以用靛蓝(I)的发色体系为例来证明,其不寻常的颜色可以很容易地用俘获取代的原理来解释。同时,这个例子表明,可以很容易地用简单的HMO模型来评估捕获替代的效果。
The principle of radical stabilization by captodative substitution recently discussed by Viehe et aZ.('l is not only of importance regarding syntheses with radicals and radicophiles but proves to be a fundamental model for understanding many properties of organic compounds. This is demonstrated using as example the chromophoric system of indigo (I), whose unusual color''] can readily be explained in terms of the principle of captodative substitution. At the same time this example shows that the effect of captodative substitution can be very easily assessed with the simple HMO model.