A New Nitrogen-Rich Energetic Material with So Many Tautomers

High Resolution Image Download MS PowerPoint Slide A new nitrogen-rich triazolo-triazole compound, (3-(6-methyl-1H-[1,2,4]triazolo[4,3- b ][1,2,4]triazol-3-yl)-1H-1,2,4-triazol-5-amine), TTT1, has been prepared, and its acid–base and tautomeric behavior has been investigated. In the pH range of 0.3–12, TTT1 can accept up to two protons, forming a monocation and a dication, and can deliver one proton, forming a monoanion. The tautomeric behavior is particularly rich for the monocation, for which computational analysis predicts four different tautomers in a narrow energy range of 2 kcal/mol. Two of these tautomers (2H-7H-8H and 3H-7H-8H) have been isolated in salts of the monocation with suitable counterions (chloride, bromide, perchlorate). Surprisingly, the most stable predicted tautomer, 1H-3H-7H, has not been found in the four crystallized salts of the monocation. The energetic perchlorate salt of the monocation (3H-7H-8H tautomer) shows good thermal stability and good stability to impact, friction, and electric discharge. The packing of this compound shows the formation of H-bonded dimers with interactions between N8–H···N1. The crystal structure of this energetic salt was studied experimentally up to 2.8 GPa; no phase change or decomposition was observed.

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Publication Details

Journal
Crystal Growth & Design
Published
2026-06-26
DOI
https://doi.org/10.1021/acs.cgd.6c00591
Primary Topic
Energetic Materials and Combustion
Type
article
Field-Weighted Citation Impact
0.00

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article

A New Nitrogen-Rich Energetic Material with So Many Tautomers

Carla Slebodnick, Roberto Centore, Nancy L. Ross, Emin Varghese et al.
Crystal Growth & Design
Energetic Materials and Combustion
article

A New Nitrogen-Rich Energetic Material with So Many Tautomers

Carla Slebodnick, Roberto Centore, Nancy L. Ross, Emin Varghese, Fatemeh Safari, Alessandro Landi, Steven D. Jacobsen, Russell J. Hemley, Santanu Chaudhuri, Jennifer Heidrich, Emmanuele Parisi, Thomas M. Klapoetke, Andrea Peluso, Carla Manfredi
article en

Abstract

High Resolution Image Download MS PowerPoint Slide A new nitrogen-rich triazolo-triazole compound, (3-(6-methyl-1H-[1,2,4]triazolo[4,3- b ][1,2,4]triazol-3-yl)-1H-1,2,4-triazol-5-amine), TTT1, has been prepared, and its acid–base and tautomeric behavior has been investigated. In the pH range of 0.3–12, TTT1 can accept up to two protons, forming a monocation and a dication, and can deliver one proton, forming a monoanion. The tautomeric behavior is particularly rich for the monocation, for which computational analysis predicts four different tautomers in a narrow energy range of 2 kcal/mol. Two of these tautomers (2H-7H-8H and 3H-7H-8H) have been isolated in salts of the monocation with suitable counterions (chloride, bromide, perchlorate). Surprisingly, the most stable predicted tautomer, 1H-3H-7H, has not been found in the four crystallized salts of the monocation. The energetic perchlorate salt of the monocation (3H-7H-8H tautomer) shows good thermal stability and good stability to impact, friction, and electric discharge. The packing of this compound shows the formation of H-bonded dimers with interactions between N8–H···N1. The crystal structure of this energetic salt was studied experimentally up to 2.8 GPa; no phase change or decomposition was observed.

Crystal Growth & Design
University of Salerno (IT), Politecnico di Torino (IT), University of Colorado Boulder (US), University of Colorado System (US), University of Illinois Chicago (US), Department of Chemistry and Earth Sciences (BY), Energetic Materials and Products Incorporation (United States) (US), Gold Skin Care Center (US), Environmental Earth Sciences (AU), University of Naples Federico II (IT), Virginia Tech (US)
National Science Foundation, U.S. Department of Energy, European Commission, University of Illinois at Urbana-Champaign, National Nuclear Security Administration, University of Illinois at Chicago, Division of Chemistry, Army Research Office, NextGenerationEU
Openalex Percentile: Top 11%
Energetic Materials and Combustion
DOIOpen Access PDFOpenAlex
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