Jump to main content
Jump to site search

Issue 3, 2013
Previous Article Next Article

Guiding the synthesis of pentazole derivatives and their mono- and di-oxides with quantum modeling

Author affiliations

Abstract

There is high prospect that derivatives of pentazole can lead to high energy density materials. However these molecules are potentially hazardous because of their high formation enthalpies and weak N–N bonds. In order to devise efficient protocols, possible schemes for the synthesis of nitro and azido derivatives of pentazole, and their mono- and di-oxides, have been explored using quantum chemical methods. Reaction pathways have been investigated in detail, with particular emphasis on locating transition states and on obtaining a reliable treatment of solvent effects. Oxidation by ozone is found to be a favorable process, leading to some regioselectivity in favor of β-mono-oxides. Nitration by NO2+BF4 is also predicted to be favorable. In contrast the electrochemical azidation of N5 and its oxidized derivatives is found to be energetically inaccessible. Combination of the individual addition and oxidation steps leads to recommendations for future synthetic work. Finally the kinetic stability of products with respect to N2 and N2O elimination is assessed.

Graphical abstract: Guiding the synthesis of pentazole derivatives and their mono- and di-oxides with quantum modeling

Back to tab navigation

Publication details

The article was received on 25 Jul 2012, accepted on 28 Nov 2012 and first published on 29 Nov 2012


Article type: Paper
DOI: 10.1039/C2NJ40649G
Citation: New J. Chem., 2013,37, 611-618
  •   Request permissions

    Guiding the synthesis of pentazole derivatives and their mono- and di-oxides with quantum modeling

    G. Frison, G. Jacob and G. Ohanessian, New J. Chem., 2013, 37, 611
    DOI: 10.1039/C2NJ40649G

Search articles by author

Spotlight

Advertisements