Issue 10, 2009

Safe 5-nitrotetrazolate anion transfer reagents

Abstract

Silver 5-nitrotetrazolate (1) and copper(II) 5-nitrotetrazolate 5-nitrotetrazole dihydrate (2) are useful reagents for the synthesis of 5-nitrotetrazole (NT) salts. Both compounds were synthesized and characterized by vibrational spectroscopy (IR and Raman) and differential scanning calorimetry (DSC). In addition, their sensitivity towards friction, shock and electrostatic discharge was tested by standard BAM methods. The extremely high sensitivity of both materials makes the transfer of the NT anion using 1 and 2 hazardous and not suitable for up-scaling. In order to diminish the hazards involved with the transfer of the energetic anion and to render the synthesis of NT salts suitable for an industrial scale the two compounds were stabilized by coordination with a chelating ligand and silver(ethylendiamine) 5-nitrotetrazolate (3) and bis(ethylendiamine)copper(II) 5-nitrotetrazolate (4) were synthesized in high yields. Both the stabilized NT anion transfer reagents were characterized by analytical and spectroscopic methods. In addition, the crystal structure of the ethylendiamine copper complex (4) was determined: orthorombic, Pbca; a = 7.5200(1), b = 14.0124(2), c = 14.7740(2) Å; V = 1556.78(4) Å3. Furthermore, we synthesized triaminocopper(II) 5-nitrotetrazolate (5), which has potential as a more environmentally-friendly primary explosive. Lastly, the synthetic potential of the ethylediamine adducts 3 and 4 to form energetic salts of NT was investigated.

Graphical abstract: Safe 5-nitrotetrazolate anion transfer reagents

Supplementary files

Article information

Article type
Paper
Submitted
24 Oct 2008
Accepted
19 Dec 2008
First published
27 Jan 2009

Dalton Trans., 2009, 1835-1841

Safe 5-nitrotetrazolate anion transfer reagents

T. M. Klapötke and C. M. Sabaté, Dalton Trans., 2009, 1835 DOI: 10.1039/B818900P

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements