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Title: Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines

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. Furthermore, 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:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2];  [3]; ORCiD logo [1];  [2]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
  2. Naval Research Lab., Washington, D.C. (United States)
  3. U.S. Army Research Lab., Aberdeen Proving Ground, MD (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (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. https://doi.org/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 = {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. Furthermore, 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 = {2017},
month = {10}
}

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    • Chemical Communications, Vol. 55, Issue 17
    • DOI: 10.1039/c8cc09653h

    Versatile coordination behaviour of the chloro-tetrazine-picolylamine ligand: mixed-valence binuclear Cu( i )/Cu( ii ) complexes
    journal, January 2019

    • Stetsiuk, Oleh; Petrusenko, Svitlana R.; Sorace, Lorenzo
    • Dalton Transactions, Vol. 48, Issue 31
    • DOI: 10.1039/c9dt02379h

    New green energetic materials based on unsymmetrically substituted pyrazole-tetrazines and their hydroperchlorates
    journal, January 2019

    • Yang, Zhen-Li; Wang, Zhen; Cao, Wen-li
    • New Journal of Chemistry, Vol. 43, Issue 47
    • DOI: 10.1039/c9nj04519h

    Rapid and High‐Yielding Formation of CL‐20/DNDAP Cocrystals via Self‐Assembly in Slightly Soluble‐Medium with Improved Sensitivity and Thermal Stability
    journal, July 2019

    • Liu, Ning; Duan, Binghui; Lu, Xianming
    • Propellants, Explosives, Pyrotechnics, Vol. 44, Issue 10
    • DOI: 10.1002/prep.201900053