Chemistry of 2,5-diaminotetrazole

Bauer, Josh; Benz, Maximilian; Klapoetke, Thomas M. and Stierstorfer, Joerg (2022): Chemistry of 2,5-diaminotetrazole. In: Dalton Transactions, Vol. 51, No. 31: pp. 11806-11813

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).

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1477-9226
• Language: English