Jump to main content
Jump to site search

Issue 12, 2015
Previous Article Next Article

Stereoelectronic source of the anomalous stability of bis-peroxides

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 03 Jul 2015, accepted on 03 Sep 2015 and first published on 07 Sep 2015


Article type: Edge Article
DOI: 10.1039/C5SC02402A
Citation: Chem. Sci., 2015,6, 6783-6791
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    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

Search articles by author