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Stable, yet “Naked”, Azo Radical Anion ArNNAr•– and Dianion ArNNAr2- (Ar = 4-CN-2,6-iPr2-C6H2) with Selective CO2 Activation

Abstract

Azo radical anion 1•– and dianion 12- have been isolated by one- and two-electron reductions of the azo compound 1 (ArNNAr, Ar = 4-CN-2,6-iPr2-C6H2) with alkali metals, respectively. The reduced species have been characterized by single-crystal X-ray analysis, EPR, UV and FT-IR spectroscopy, as well as SQUID measurements. The filling of one and two electrons in the π* orbital of N–N double bond of 1 leads to a half-double N–N bond in 1•– and a single N–N bond in 12-. The uncoordinated nature enables these reduced species to activate CO2. The exposure of 1•– solution to CO2 led to the formation of oxalate anion C2O42-, while that of 12- solution to CO2 afforded the hydrazine dicarboxylate dianion [1-2CO2]2-, which reversiably dissociated back to 1 and CO2 upon oxidation.

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Supplementary files

Article information


Submitted
19 Sep 2019
Accepted
10 Feb 2020
First published
10 Feb 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Stable, yet “Naked”, Azo Radical Anion ArNNAr•– and Dianion ArNNAr2- (Ar = 4-CN-2,6-iPr2-C6H2) with Selective CO2 Activation

X. Wang, W. Wang, G. Tan, R. Feng, Y. Fang, C. Chen, H. Ruan and Y. Zhao, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/C9CC07382E

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