N-Acetimidamide Functionalized 4-Amino-3,5-dinitropyrazole as an Oxygen-Containing Cation for Thermally Stable
Priyanka Das1, Prachi Bhatia1, Meera Khatri1
1Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand 247667, India.
The Journal of Organic Chemistry
|December 19, 2025
Summary
Researchers developed novel oxygen-rich cations for ionic energetic materials (IEMs), enhancing both energy and stability. This breakthrough addresses limitations of traditional IEMs, paving the way for safer and more powerful energetic materials.
Area of Science:
- Materials Science
- Chemistry
Background:
- Ionic energetic materials (IEMs) offer a strategy to balance performance and stability.
- Existing IEMs often suffer from reduced oxygen balance, density, and performance.
- Oxygen-containing cations are underexplored due to complex synthesis but can mitigate these issues.
Purpose of the Study:
- To synthesize novel oxygen-containing cationic precursors for IEMs.
- To create and characterize new energetic salts using these precursors.
- To evaluate the energetic and stability properties of the synthesized IEMs.
Main Methods:
- Synthesized a novel oxygen-containing cationic precursor via N-functionalization of 4-amino-3,5-dinitropyrazole (ADNP).
- Prepared various energetic salts by combining the novel cation with N, O-rich anions.
- Characterized compounds using NMR, IR, elemental analysis, and single-crystal XRD for select samples.
Main Results:
- Synthesized novel ADNP-based oxygen-rich cations and derived energetic salts.
- Achieved significant improvements in density and oxygen balance (OB) compared to N-rich cations.
- Demonstrated enhanced thermal and physical stability of the synthesized IEMs.
Conclusions:
- Developed a viable strategy using oxygen-rich cations to overcome the energy-stability trade-off in IEMs.
- The novel IEMs exhibit superior energetic and stability properties.
- This research advances the field of ionic energetic materials, encouraging further development.
Related Concept Videos
01:19Diazonium Group Substitution: –OH and –H
3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.2K
01:371° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
4.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.7K
01:19Amines to Amides: Acylation of Amines
3.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.4K
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.6K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.6K
01:261° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
3.8K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
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...
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...
3.8K
02:42Acidity of 1-Alkynes
11.0K
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
11.0K