Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines
Abstract
Abstract The reaction of 3,4‐dinitropyrazole, 5‐nitrotetrazole, or 4‐nitro‐1,2,3‐triazole with 1,2,4,5‐tetrazines substituted with 3,5‐dimethylpyrazolyl (dmp) groups results in energetic cocrystals after 1 minute of reflux and cooling to room temperature in yields of 89–92 %. Hydrogen‐bonding between the dmp group to the N−H of the energetic heterocycles are the predominant interaction that stabilizes the new cocrystals. Each cocrystal packs in a different lattice structure and the cocrystals with sheet‐like and herring‐bone crystal packing orientations are less sensitive than the cocrystal with the interlocked structure. Electrostatic potential mapping helps rationalize why dmp‐substituted tetrazines readily form cocrystals, whereas more electron‐deficient pyrazolyl tetrazines do not. The calculated energetic performance of the new cocrystals approaches that of 2,4,6‐trinitrotoluene (TNT) and importantly, these materials will aid in the rational design of new cocrystalline energetic materials.
- Authors:
-
[1];
[1];
[2];
[1];
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
- Naval Research Lab., Washington, D.C. (United States)
- U.S. Army Research Lab., Aberdeen Proving Ground, MD (United States)
- Publication Date:
- Research Org.:
- Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
- Sponsoring Org.:
- USDOE Laboratory Directed Research and Development (LDRD) Program
- OSTI Identifier:
- 1477712
- Alternate Identifier(s):
- OSTI ID: 1405546
- Report Number(s):
- LA-UR-17-28237
Journal ID: ISSN 0947-6539
- Grant/Contract Number:
- AC52-06NA25396
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Volume: 23; Journal Issue: 65; Journal ID: ISSN 0947-6539
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Material Science; Organic Chemistry; cocrystal; dimethylpyrazolyl; energetic materials; hydrogen-bonding; tetrazine
Citation Formats
Snyder, Christopher J., Chavez, David E., Imler, Gregory H., Byrd, Edward F. C., Leonard, Philip W., and Parrish, Damon A. Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines. United States: N. p., 2017.
Web. doi:10.1002/chem.201704394.
Snyder, Christopher J., Chavez, David E., Imler, Gregory H., Byrd, Edward F. C., Leonard, Philip W., & Parrish, Damon A. Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines. United States. https://doi.org/10.1002/chem.201704394
Snyder, Christopher J., Chavez, David E., Imler, Gregory H., Byrd, Edward F. C., Leonard, Philip W., and Parrish, Damon A. Mon .
"Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines". United States. https://doi.org/10.1002/chem.201704394. https://www.osti.gov/servlets/purl/1477712.
@article{osti_1477712,
title = {Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines},
author = {Snyder, Christopher J. and Chavez, David E. and Imler, Gregory H. and Byrd, Edward F. C. and Leonard, Philip W. and Parrish, Damon A.},
abstractNote = {Abstract The reaction of 3,4‐dinitropyrazole, 5‐nitrotetrazole, or 4‐nitro‐1,2,3‐triazole with 1,2,4,5‐tetrazines substituted with 3,5‐dimethylpyrazolyl (dmp) groups results in energetic cocrystals after 1 minute of reflux and cooling to room temperature in yields of 89–92 %. Hydrogen‐bonding between the dmp group to the N−H of the energetic heterocycles are the predominant interaction that stabilizes the new cocrystals. Each cocrystal packs in a different lattice structure and the cocrystals with sheet‐like and herring‐bone crystal packing orientations are less sensitive than the cocrystal with the interlocked structure. Electrostatic potential mapping helps rationalize why dmp‐substituted tetrazines readily form cocrystals, whereas more electron‐deficient pyrazolyl tetrazines do not. The calculated energetic performance of the new cocrystals approaches that of 2,4,6‐trinitrotoluene (TNT) and importantly, these materials will aid in the rational design of new cocrystalline energetic materials.},
doi = {10.1002/chem.201704394},
journal = {Chemistry - A European Journal},
number = 65,
volume = 23,
place = {United States},
year = {Mon Oct 02 00:00:00 EDT 2017},
month = {Mon Oct 02 00:00:00 EDT 2017}
}
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