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

Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H.; Byrd, Edward F. C.; Leonard, Philip W.; Parrish, Damon A.

doi:10.1002/chem.201704394

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

Journal Article · Mon Oct 02 00:00:00 EDT 2017 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.201704394· OSTI ID:1477712

^[1];

^[2]; Byrd, Edward F. C. ^[3];

^[1]; Parrish, Damon A. ^[2]

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)

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.

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Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE Laboratory Directed Research and Development (LDRD) Program

Grant/Contract Number:: AC52-06NA25396

OSTI ID:: 1477712

Alternate ID(s):: OSTI ID: 1405546

Report Number(s):: LA-UR-17-28237

Journal Information:: Chemistry - A European Journal, Vol. 23, Issue 65; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 20 works

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A toxological study of 3,6-BIS(3,5-Dimethyl-1-1-Pyrazolyl)1,2-Dihydro-1,2,4,5-Tetrazine

Technical Report · Mon Mar 01 00:00:00 EST 1993 · OSTI ID:1477712

London, J E

A toxological study of 3,6-BIS(3,5-Dimethyl-1-1-Pyrazolyl)1,2-Dihydro-1,2,4,5-Tetrazine

Technical Report · Mon Mar 01 00:00:00 EST 1993 · OSTI ID:1477712

London, J E

Azido and tetrazolo 1,2,4,5-tetrazine N-oxides

Journal Article · Thu Feb 23 00:00:00 EST 2017 · Angewandte Chemie (International Edition) · OSTI ID:1477712

Chavez, David E.; Parrish, Damon A.; Mitchell, Lauren; +1 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Material Science
Organic Chemistry
cocrystal
dimethylpyrazolyl
energetic materials
hydrogen-bonding
tetrazine

CCDC 1574146: Experimental Crystal Structure Determination: HETTOS : 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine bis(5-nitro-2H-tetrazole) Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H. https://doi.org/10.5517/ccdc.csd.cc1pv0xg The current record is supplemented by this dataset	dataset	September 2017
CCDC 1574145: Experimental Crystal Structure Determination: HETTIM : 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine bis(3,4-dinitro-1H-pyrazole) Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H. https://doi.org/10.5517/ccdc.csd.cc1pv0wf The current record is supplemented by this dataset	dataset	September 2017
CCDC 1574147: Experimental Crystal Structure Determination: HETTUY : 6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-amine 4-nitro-2H-1,2,3-triazole Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H. https://doi.org/10.5517/ccdc.csd.cc1pv0yh The current record is supplemented by this dataset	dataset	September 2017