Related Experiment Video
Updated: Jan 15, 2026

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Zwitterionic Energetic Compound Based on N-Acetamidinium Functionalized Nitroimino-tetrazole: Towards
Priyanka Das1, Prachi Bhatia1, Dheeraj Kumar1
1Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand, 247667, India.
None:
In this work, an advanced high-performing zwitterionic compound (E)-4-(2-amino-2-iminioethyl)-5-(nitroimino)-4,5-dihydrotetrazol-1-ide (3) was achieved, where negatively charged nitroimino-tetrazolate moiety is linked with positively charged acetamidinium group via N-functionalization technique. A comparative study was also carried out to justify the superlative properties of compound 3 (Td = 152 °C; ρ = 1.83 g cm-3; Dv = 8823 m s-1) with respect to its salt analogue 5 (Td = 90 °C; ρ = 1.65 g cm-3; Dv = 8183 m s-1), which exhibited adequate thermal stability and excellent energetic performances. Additionally, the zwitterionic structure of 3 was confirmed by single-crystal X-ray analysis and differences in overall stability was investigated using electrostatic potential (ESP) and reduced density gradient (RDG) analysis, relative to the neutral nitroimino-tetrazole (NATz).
Related Concept Videos
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
2° Amines to N-Nitrosamines: Reaction with NaNO2
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Diazonium Group Substitution: –OH and –H
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

