Chemistry of 2,5-diaminotetrazole
Josh Bauer1, Maximilian Benz1, Thomas M Klapötke1
1Department of Chemistry, Ludwig-Maximilian University Munich, Butenandtstr. 5-13, 81377 Munich, Germany. tmk@cup.uni-muenchen.de.
Abstract:
1,5-Diaminotetrazole is one of the most prominent high-nitrogen tetrazole compounds described in the literature. Interestingly the isomer 2,5-diaminotetrazole is nearly undescribed due to its challenging synthetic routes. 2,5-Diaminotetrazol (1) was successfully synthesized via amination of 5-aminotetrazole followed by various purification steps to separate it from isomeric 1,5-diaminotetrazole. In addition to the extensive characterization of 2,5-DAT further derivates by protonation, methylation and amination of the tetrazole ring were synthesized and characterized. The resulting tri-functionalized, ionic tetrazolium derivatives were combined with energetic anions (nitrate, perchlorate, azide, 5,5'-bistetrazole-1,1'-diolate (BTO2)) to adjust and tune the properties of each compound. All compounds were intensively characterized including IR and multinuclear NMR spectroscopy, thermal analysis through DTA, X-ray diffraction and sensitivity testing. The purity was verified by CHNO elemental analysis and the energetic properties were calculated using the EXPLO5 code and the calculated enthalpy of formation (CBS-4M).
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