Stable Diporphyrinylaminyl Radical and Nitrenium Ion,Angewandte Chemie International Edition

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Stable Diporphyrinylaminyl Radical and Nitrenium Ion
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-06-27 , DOI: 10.1002/anie.201805385
Daiki Shimizu ₁ , Keisuke Fujimoto ₁ , Atsuhiro Osuka ₁

Affiliation

Nitrenium ions, isoelectronic nitrogen counterparts of carbenes, are important intermediates in various biological and chemical processes. Herein we describe the first synthesis and characterization of a stable nitrenium ion without resonance stabilization by adjoining amino groups. Namely, a stable salt of a diporphyrinylnitrenium ion was synthesized by stepwise oxidation of the corresponding diporphyrinylamine through a stable aminyl radical. The nitrenium ion exhibits characteristic features such as a singlet ground state, enhanced double‐bond character of the central C−N bonds, no reactivity toward water and methanol, and negative solvatochromic behavior.

中文翻译：

稳定的双卟啉亚胺基自由基和镍离子

氮离子是卡宾的等电子氮对应物，是各种生物和化学过程中的重要中间体。在本文中，我们描述了通过结合氨基而没有共振稳定的稳定氮离子的首次合成和表征。即，通过使相应的二卟啉胺通过稳定的氨基自由基逐步氧化，合成了二卟啉基氮鎓离子的稳定盐。ion离子具有特征性特征，例如单线基态，中心CN键的增强双键特性，对水和甲醇无反应性以及负溶剂化行为。

更新日期：2018-06-27

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