5‐(1H‐Tetrazolyl)‐2‐Hydroxy‐Tetrazole: A Selective 2N‐Monoxidation of Bis(1H‐Tetrazole)
Abstract
Sodium 5‐cyanotetrazolate sesquihydrate (1) is prepared from sodium azide and two equivalents of sodium cyanide under acidic conditions. 1 is then N‐oxidized with Oxone to sodium 5‐cyanotetrazolate monohydrate (2). Compound 2 is treated with sodium azide and a Lewis acid to form 5‐(1H‐tetrazolyl)‐2‐hydroxytetrazole monohydrate (3). Compound 3 can be deprotonated twice by various bases to give ionic derivatives such as the bis(hydroxylammonium) (4), bis(hydrazinium) (6), bis(guanidinium) (7), bis(aminoguanidinium) (8), bis(ammonium) (9), and diaminouronium (11) salt. In addition, compound 3 can only be deprotonated once, as demonstrated by the hydroxylammonium (4) and triaminoguanidinium (10) salts. Compounds 2–5 and 10–11 are structurally characterized by single‐crystal X‐ray diffraction. Additionally, compounds 2–11 are characterized by using NMR and vibrational (IR, Raman) spectroscopy as well as mass spectrometry and elemental analysis. Their thermal behaviors are studied from differential thermal analysis measurements, and the sensitivities of the compounds toward shock, friction, and electrostatic discharge are determined. In addition, the heats of formation are calculated (atomization method, CBS‐4M enthalpies), and several detonation/propulsion parameters are computed with the EXPLO5 code.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Aug 19, 2014
- Source ID
- 10.1002/cplu.201402124
Entities
People
- Jörg Stierstorfer
- Matthias Q. Kurz
- Muhamed Sućeska
- Philipp C. Schmid
- Regina Scharf
- Thomas M. Klapötke
Organizations
- Australian RL Commission
- Ludwig-Maximilians-Universität München
- Office of Naval Research
- United States Army Armament Research, Development and Engineering Center
- United States Army Research Laboratory