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Issue 12, 2015
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Stereoelectronic source of the anomalous stability of bis-peroxides

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Abstract

The unusual stability of bis- and tris-peroxides contradicts the conventional wisdom – some of them can melt without decomposition at temperatures exceeding 100 °C. In this work, we disclose a stabilizing stereoelectronic effect that two peroxide groups can exert on each other. This stabilization originates from strong anomeric nO → σ*CO interactions that are absent in mono-peroxides but reintroduced in molecules where two peroxide moieties are separated by a CH2 group. Furthermore, such effects can be induced by other σ-acceptors and amplified by structural constraints imposed by cyclic and bicyclic frameworks.

Graphical abstract: Stereoelectronic source of the anomalous stability of bis-peroxides

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Supplementary files

Article information


Submitted
03 Jul 2015
Accepted
03 Sep 2015
First published
07 Sep 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 6783-6791
Article type
Edge Article
Author version available

Stereoelectronic source of the anomalous stability of bis-peroxides

G. D. P. Gomes, V. Vil', A. Terent'ev and I. V. Alabugin, Chem. Sci., 2015, 6, 6783
DOI: 10.1039/C5SC02402A

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