skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Abstract

This paper presents the synthesis and characterization of the oxidation products of 3,6-diazido-1,2,4,5-tetrazine (1) and 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine (2). 3,6-Diazido-1,2,4,5-tetrazine-1,4-dioxide was produced from oxidation with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to two different products, 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine mono-N-oxide and di-N-oxide. These N-oxide compounds display promising performance properties as energetic materials.

Authors:
ORCiD logo [1];  [2];  [3];  [2]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
  2. Naval Research Lab., Washington, D.C. (United States)
  3. Univ. of Minnesota, Minneapolis, MN (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:
1353024
Report Number(s):
LA-UR-16-29593
Journal ID: ISSN 1433-7851
Grant/Contract Number:  
AC52-06NA25396
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 13; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 1,2,4,5-tetrazine; azides; energetic materials; N-oxides; tetrazole

Citation Formats

Chavez, David E., Parrish, Damon A., Mitchell, Lauren, and Imler, Greg H. Azido and tetrazolo 1,2,4,5-tetrazine N-oxides. United States: N. p., 2017. Web. doi:10.1002/anie.201612496.
Chavez, David E., Parrish, Damon A., Mitchell, Lauren, & Imler, Greg H. Azido and tetrazolo 1,2,4,5-tetrazine N-oxides. United States. doi:10.1002/anie.201612496.
Chavez, David E., Parrish, Damon A., Mitchell, Lauren, and Imler, Greg H. Thu . "Azido and tetrazolo 1,2,4,5-tetrazine N-oxides". United States. doi:10.1002/anie.201612496. https://www.osti.gov/servlets/purl/1353024.
@article{osti_1353024,
title = {Azido and tetrazolo 1,2,4,5-tetrazine N-oxides},
author = {Chavez, David E. and Parrish, Damon A. and Mitchell, Lauren and Imler, Greg H.},
abstractNote = {This paper presents the synthesis and characterization of the oxidation products of 3,6-diazido-1,2,4,5-tetrazine (1) and 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine (2). 3,6-Diazido-1,2,4,5-tetrazine-1,4-dioxide was produced from oxidation with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to two different products, 6-amino-[1,5-b]tetrazolo-1,2,4,5-tetrazine mono-N-oxide and di-N-oxide. These N-oxide compounds display promising performance properties as energetic materials.},
doi = {10.1002/anie.201612496},
journal = {Angewandte Chemie (International Edition)},
number = 13,
volume = 56,
place = {United States},
year = {2017},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 32 works
Citation information provided by
Web of Science

Figures / Tables:

Figure 1 Figure 1: Azido/tetrazolo isomerization of azido-­1,2,4,5-­tetrazines.

Save / Share:

Works referenced in this record:

Chlorine-Free Red-Burning Pyrotechnics
journal, August 2015

  • Sabatini, Jesse J.; Koch, Ernst-Christian; Poret, Jay C.
  • Angewandte Chemie International Edition, Vol. 54, Issue 37
  • DOI: 10.1002/anie.201505829

An Energetic Triazolo-1,2,4-Triazine and its N-Oxide
journal, November 2016

  • Piercey, Davin G.; Chavez, David E.; Scott, Brian L.
  • Angewandte Chemie International Edition, Vol. 55, Issue 49
  • DOI: 10.1002/anie.201608723

Recent Advances in the Synthesis of High Explosive Materials
journal, December 2015


Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)
journal, July 2016

  • Klenov, Michael S.; Guskov, Alexey A.; Anikin, Oleg V.
  • Angewandte Chemie International Edition, Vol. 55, Issue 38
  • DOI: 10.1002/anie.201605611

N -Oxide 1,2,4,5-Tetrazine-Based High-Performance Energetic Materials
journal, October 2014

  • Wei, Hao; Gao, Haixiang; Shreeve, Jean'ne M.
  • Chemistry - A European Journal, Vol. 20, Issue 51
  • DOI: 10.1002/chem.201405122

Independent Control of Optical and Explosive Properties: Pyrazole–Tetrazine Complexes of First Row Transition Metals
journal, August 2015


Improved green-light-emitting pyrotechnic formulations based on tris(2,2,2-trinitroethyl)borate and boron carbide
journal, January 2014

  • Klapötke, Thomas M.; Krumm, Burkhard; Rusan, Magdalena
  • Chem. Commun., Vol. 50, Issue 67
  • DOI: 10.1039/C4CC04616A

Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations
journal, May 2009

  • Byrd, Edward F. C.; Rice, Betsy M.
  • The Journal of Physical Chemistry A, Vol. 113, Issue 19
  • DOI: 10.1021/jp806520b

Bis(4-nitraminofurazanyl-3-azoxy)azofurazan and Derivatives: 1,2,5-Oxadiazole Structures and High-Performance Energetic Materials
journal, August 2016


Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
journal, November 2016

  • Fischer, Dennis; Gottfried, Jennifer L.; Klapötke, Thomas M.
  • Angewandte Chemie, Vol. 128, Issue 52
  • DOI: 10.1002/ange.201609267

Insensitive High Explosives II: 3,3′‐Diamino‐4,4′‐azoxyfurazan (DAAF)
journal, April 2016


Electroactive Explosives: Nitrate Ester-Functionalized 1,2,4,5-Tetrazines
journal, May 2013

  • Chavez, David E.; Hanson, Susan K.; Veauthier, Jacqueline M.
  • Angewandte Chemie, Vol. 125, Issue 27
  • DOI: 10.1002/ange.201302128

Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations
journal, January 2006

  • Byrd, Edward F. C.; Rice, Betsy M.
  • The Journal of Physical Chemistry A, Vol. 110, Issue 3
  • DOI: 10.1021/jp0536192

Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System
journal, September 2015

  • Chavez, David E.; Bottaro, Jeffery C.; Petrie, Mark
  • Angewandte Chemie International Edition, Vol. 54, Issue 44
  • DOI: 10.1002/anie.201506744

Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures
journal, June 1986

  • Rozen, Shlomo; Brand, Michael
  • Angewandte Chemie International Edition in English, Vol. 25, Issue 6
  • DOI: 10.1002/anie.198605541

Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound
journal, September 2005

  • Huynh, My Hang V.; Hiskey, Michael A.; Chavez, David E.
  • Journal of the American Chemical Society, Vol. 127, Issue 36
  • DOI: 10.1021/ja0509735

Bis(4-nitraminofurazanyl-3-azoxy)azofurazan and Derivatives: 1,2,5-Oxadiazole Structures and High-Performance Energetic Materials
journal, August 2016

  • Liu, Yuji; Zhang, Jiaheng; Wang, Kangcai
  • Angewandte Chemie International Edition, Vol. 55, Issue 38
  • DOI: 10.1002/anie.201606378

Energetic Chromophores: Low-Energy Laser Initiation in Explosive Fe(II) Tetrazine Complexes
journal, March 2016

  • Myers, Thomas W.; Bjorgaard, Josiah A.; Brown, Kathryn E.
  • Journal of the American Chemical Society, Vol. 138, Issue 13
  • DOI: 10.1021/jacs.6b02155

Photoactive Excited States in Explosive Fe(II) Tetrazine Complexes: A Time-Dependent Density Functional Theory Study
journal, December 2016

  • Sifain, Andrew E.; Bjorgaard, Josiah A.; Myers, Thomas W.
  • The Journal of Physical Chemistry C, Vol. 120, Issue 50
  • DOI: 10.1021/acs.jpcc.6b10333

Synthesis, Characterization, and Energetic Properties of 6-Amino-tetrazolo[1,5-b]-1,2,4,5-tetrazine-7- N -oxide: A Nitrogen-Rich Material with High Density
journal, March 2015

  • Wei, Hao; Zhang, Jiaheng; Shreeve, Jean'ne M.
  • Chemistry - An Asian Journal, Vol. 10, Issue 5
  • DOI: 10.1002/asia.201500086

Elemental Fluorine:  Not Only for Fluoroorganic Chemistry!
journal, January 1996

  • Rozen, Shlomo
  • Accounts of Chemical Research, Vol. 29, Issue 5
  • DOI: 10.1021/ar950106c

Rote pyrotechnische Leuchtsätze - ohne Chlor!
journal, August 2015

  • Sabatini, Jesse J.; Koch, Ernst-Christian; Poret, Jay C.
  • Angewandte Chemie, Vol. 127, Issue 37
  • DOI: 10.1002/ange.201505829

The Taming of CN7−: The Azidotetrazolate 2-Oxide Anion
journal, October 2011

  • Klapötke, Thomas M.; Piercey, Davin G.; Stierstorfer, Jörg
  • Chemistry - A European Journal, Vol. 17, Issue 46
  • DOI: 10.1002/chem.201102064

Cover Picture: Kinetic Passivation Effect of Localized Differential Aeration on Brass (ChemPlusChem 1/2016)
journal, December 2015

  • Kuznetsov, Volodymyr; Estrada-Vargas, Arturo; Maljusch, Artjom
  • ChemPlusChem, Vol. 81, Issue 1
  • DOI: 10.1002/cplu.201500521

A Highly Stable and Insensitive Fused Triazolo-Triazine Explosive (TTX)
journal, December 2016

  • Kumar, Dheeraj; Imler, Gregory H.; Parrish, Damon A.
  • Chemistry - A European Journal, Vol. 23, Issue 8
  • DOI: 10.1002/chem.201604919

Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)
journal, July 2016

  • Klenov, Michael S.; Guskov, Alexey A.; Anikin, Oleg V.
  • Angewandte Chemie, Vol. 128, Issue 38
  • DOI: 10.1002/ange.201605611

Covalent and Ionic Insensitive High‐Explosives
journal, May 2016

  • Klapötke, Thomas M.; Witkowski, Tomasz G.
  • Propellants, Explosives, Pyrotechnics, Vol. 41, Issue 3
  • DOI: 10.1002/prep.201600006

An Energetic Triazolo-1,2,4-Triazine and its N-Oxide
journal, November 2016

  • Piercey, Davin G.; Chavez, David E.; Scott, Brian L.
  • Angewandte Chemie, Vol. 128, Issue 49
  • DOI: 10.1002/ange.201608723

Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
journal, November 2016

  • Fischer, Dennis; Gottfried, Jennifer L.; Klapötke, Thomas M.
  • Angewandte Chemie International Edition, Vol. 55, Issue 52
  • DOI: 10.1002/anie.201609267

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds
journal, May 2016


1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N 10 Chain
journal, April 2011

  • Klapötke, Thomas M.; Piercey, Davin G.
  • Inorganic Chemistry, Vol. 50, Issue 7
  • DOI: 10.1021/ic200071q

1,2,4,5-tetrazine based energetic materials
journal, December 1999


Two-Photon Absorption in Conjugated Energetic Molecules
journal, June 2016

  • Bjorgaard, Josiah A.; Sifain, Andrew E.; Nelson, Tammie
  • The Journal of Physical Chemistry A, Vol. 120, Issue 26
  • DOI: 10.1021/acs.jpca.6b03136

Nitrotetrazolate-2 N -oxides and the Strategy of N -Oxide Introduction
journal, December 2010

  • Göbel, Michael; Karaghiosoff, Konstantin; Klapötke, Thomas M.
  • Journal of the American Chemical Society, Vol. 132, Issue 48
  • DOI: 10.1021/ja106892a

The CN 7 Anion
journal, January 2009

  • Klapötke, Thomas M.; Stierstorfer, Jörg
  • Journal of the American Chemical Society, Vol. 131, Issue 3
  • DOI: 10.1021/ja8077522

Electroactive Explosives: Nitrate Ester-Functionalized 1,2,4,5-Tetrazines
journal, May 2013

  • Chavez, David E.; Hanson, Susan K.; Veauthier, Jacqueline M.
  • Angewandte Chemie International Edition, Vol. 52, Issue 27
  • DOI: 10.1002/anie.201302128

Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System
journal, September 2015

  • Chavez, David E.; Bottaro, Jeffery C.; Petrie, Mark
  • Angewandte Chemie, Vol. 127, Issue 44
  • DOI: 10.1002/ange.201506744

    Works referencing / citing this record:

    CCDC 1522798: Experimental Crystal Structure Determination: XALDUM : 2,5-dioxo-2,5-tetrazolo[1,5-b][1,2,4,5]tetrazin-6-amine
    dataset, December 2016


    Electroactive Explosives: Nitrate Ester-Functionalized 1,2,4,5-Tetrazines
    journal, May 2013

    • Chavez, David E.; Hanson, Susan K.; Veauthier, Jacqueline M.
    • Angewandte Chemie, Vol. 125, Issue 27
    • DOI: 10.1002/ange.201302128

    Rote pyrotechnische Leuchtsätze - ohne Chlor!
    journal, August 2015

    • Sabatini, Jesse J.; Koch, Ernst-Christian; Poret, Jay C.
    • Angewandte Chemie, Vol. 127, Issue 37
    • DOI: 10.1002/ange.201505829

    Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System
    journal, September 2015

    • Chavez, David E.; Bottaro, Jeffery C.; Petrie, Mark
    • Angewandte Chemie, Vol. 127, Issue 44
    • DOI: 10.1002/ange.201506744

    Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)
    journal, July 2016

    • Klenov, Michael S.; Guskov, Alexey A.; Anikin, Oleg V.
    • Angewandte Chemie, Vol. 128, Issue 38
    • DOI: 10.1002/ange.201605611

    Bis(4-nitraminofurazanyl-3-azoxy)azofurazan and Derivatives: 1,2,5-Oxadiazole Structures and High-Performance Energetic Materials
    journal, August 2016


    An Energetic Triazolo-1,2,4-Triazine and its N-Oxide
    journal, November 2016

    • Piercey, Davin G.; Chavez, David E.; Scott, Brian L.
    • Angewandte Chemie, Vol. 128, Issue 49
    • DOI: 10.1002/ange.201608723

    Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
    journal, November 2016

    • Fischer, Dennis; Gottfried, Jennifer L.; Klapötke, Thomas M.
    • Angewandte Chemie, Vol. 128, Issue 52
    • DOI: 10.1002/ange.201609267

    Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures
    journal, June 1986

    • Rozen, Shlomo; Brand, Michael
    • Angewandte Chemie International Edition in English, Vol. 25, Issue 6
    • DOI: 10.1002/anie.198605541

    Electroactive Explosives: Nitrate Ester-Functionalized 1,2,4,5-Tetrazines
    journal, May 2013

    • Chavez, David E.; Hanson, Susan K.; Veauthier, Jacqueline M.
    • Angewandte Chemie International Edition, Vol. 52, Issue 27
    • DOI: 10.1002/anie.201302128

    Chlorine-Free Red-Burning Pyrotechnics
    journal, August 2015

    • Sabatini, Jesse J.; Koch, Ernst-Christian; Poret, Jay C.
    • Angewandte Chemie International Edition, Vol. 54, Issue 37
    • DOI: 10.1002/anie.201505829

    Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System
    journal, September 2015

    • Chavez, David E.; Bottaro, Jeffery C.; Petrie, Mark
    • Angewandte Chemie International Edition, Vol. 54, Issue 44
    • DOI: 10.1002/anie.201506744

    Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)
    journal, July 2016

    • Klenov, Michael S.; Guskov, Alexey A.; Anikin, Oleg V.
    • Angewandte Chemie International Edition, Vol. 55, Issue 38
    • DOI: 10.1002/anie.201605611

    Bis(4-nitraminofurazanyl-3-azoxy)azofurazan and Derivatives: 1,2,5-Oxadiazole Structures and High-Performance Energetic Materials
    journal, August 2016

    • Liu, Yuji; Zhang, Jiaheng; Wang, Kangcai
    • Angewandte Chemie International Edition, Vol. 55, Issue 38
    • DOI: 10.1002/anie.201606378

    An Energetic Triazolo-1,2,4-Triazine and its N-Oxide
    journal, November 2016

    • Piercey, Davin G.; Chavez, David E.; Scott, Brian L.
    • Angewandte Chemie International Edition, Vol. 55, Issue 49
    • DOI: 10.1002/anie.201608723

    Synthesis and Investigation of Advanced Energetic Materials Based on Bispyrazolylmethanes
    journal, November 2016

    • Fischer, Dennis; Gottfried, Jennifer L.; Klapötke, Thomas M.
    • Angewandte Chemie International Edition, Vol. 55, Issue 52
    • DOI: 10.1002/anie.201609267

    Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability
    journal, June 2017

    • Yin, Ping; Zhang, Jiaheng; Imler, Gregory H.
    • Angewandte Chemie International Edition, Vol. 56, Issue 30
    • DOI: 10.1002/anie.201704687

    Synthesis, Characterization, and Energetic Properties of 6-Amino-tetrazolo[1,5-b]-1,2,4,5-tetrazine-7- N -oxide: A Nitrogen-Rich Material with High Density
    journal, March 2015

    • Wei, Hao; Zhang, Jiaheng; Shreeve, Jean'ne M.
    • Chemistry - An Asian Journal, Vol. 10, Issue 5
    • DOI: 10.1002/asia.201500086

    The Chemistry and Properties of Energetic Materials Bearing [1,2,4]Triazolo[4,3- b ][1,2,4,5]tetrazine Fused Rings
    journal, October 2018

    • Wang, Guilong; Lu, Tian; Fan, Guijuan
    • Chemistry - An Asian Journal, Vol. 13, Issue 23
    • DOI: 10.1002/asia.201801145

    Comparison of 1‐Ethyl‐5 H ‐tetrazole and 1‐Azidoethyl‐5 H ‐tetrazole as Ligands in Energetic Transition Metal Complexes
    journal, April 2019

    • Wurzenberger, Maximilian H. H.; Gruhne, Michael S.; Lommel, Marcus
    • Chemistry – An Asian Journal, Vol. 14, Issue 11
    • DOI: 10.1002/asia.201900269

    The Taming of CN7−: The Azidotetrazolate 2-Oxide Anion
    journal, October 2011

    • Klapötke, Thomas M.; Piercey, Davin G.; Stierstorfer, Jörg
    • Chemistry - A European Journal, Vol. 17, Issue 46
    • DOI: 10.1002/chem.201102064

    N -Oxide 1,2,4,5-Tetrazine-Based High-Performance Energetic Materials
    journal, October 2014

    • Wei, Hao; Gao, Haixiang; Shreeve, Jean'ne M.
    • Chemistry - A European Journal, Vol. 20, Issue 51
    • DOI: 10.1002/chem.201405122

    A Highly Stable and Insensitive Fused Triazolo-Triazine Explosive (TTX)
    journal, December 2016

    • Kumar, Dheeraj; Imler, Gregory H.; Parrish, Damon A.
    • Chemistry - A European Journal, Vol. 23, Issue 8
    • DOI: 10.1002/chem.201604919

    Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide
    journal, October 2017

    • Tang, Yongxing; He, Chunlin; Imler, Gregory H.
    • Chemistry - A European Journal, Vol. 23, Issue 60
    • DOI: 10.1002/chem.201703930

    Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines
    journal, October 2017

    • Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H.
    • Chemistry - A European Journal, Vol. 23, Issue 65
    • DOI: 10.1002/chem.201704394

    Cover Picture: Kinetic Passivation Effect of Localized Differential Aeration on Brass (ChemPlusChem 1/2016)
    journal, December 2015

    • Kuznetsov, Volodymyr; Estrada-Vargas, Arturo; Maljusch, Artjom
    • ChemPlusChem, Vol. 81, Issue 1
    • DOI: 10.1002/cplu.201500521

    Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine: Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine
    journal, May 2018

    • Tang, Yongxing; He, Chunlin; Yin, Ping
    • European Journal of Organic Chemistry, Vol. 2018, Issue 19
    • DOI: 10.1002/ejoc.201800347

    Synthesis and Properties of Energetic Materials Based on 1,3-Diazocyclopentane: Synthesis and Properties of Energetic Materials Based on 1,3-Diazocyclopentane
    journal, December 2018

    • Jin, Xinghui; Xiao, Menghui; Wang, Changying
    • European Journal of Organic Chemistry, Vol. 2019, Issue 5
    • DOI: 10.1002/ejoc.201801525

    An Energetic (Nitro- NNO -azoxy)triazolo-1,2,4-triazine : An Energetic (Nitro-
    journal, June 2019

    • Anikin, Oleg V.; Leonov, Nikita E.; Klenov, Michael S.
    • European Journal of Organic Chemistry, Vol. 2019, Issue 26
    • DOI: 10.1002/ejoc.201900314

    Covalent and Ionic Insensitive High‐Explosives
    journal, May 2016

    • Klapötke, Thomas M.; Witkowski, Tomasz G.
    • Propellants, Explosives, Pyrotechnics, Vol. 41, Issue 3
    • DOI: 10.1002/prep.201600006

    Insensitive High Explosives II: 3,3′‐Diamino‐4,4′‐azoxyfurazan (DAAF)
    journal, April 2016


    A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds
    journal, May 2016


    Synthesis of 4,8-Dinitraminodifurazano[3, 4- b,e ]pyrazine Derived Nitrogen-Rich Salts as Potential Energetic Materials
    journal, January 2018


    Independent Control of Optical and Explosive Properties: Pyrazole–Tetrazine Complexes of First Row Transition Metals
    journal, August 2015


    Two-Photon Absorption in Conjugated Energetic Molecules
    journal, June 2016

    • Bjorgaard, Josiah A.; Sifain, Andrew E.; Nelson, Tammie
    • The Journal of Physical Chemistry A, Vol. 120, Issue 26
    • DOI: 10.1021/acs.jpca.6b03136

    Photoactive Excited States in Explosive Fe(II) Tetrazine Complexes: A Time-Dependent Density Functional Theory Study
    journal, December 2016

    • Sifain, Andrew E.; Bjorgaard, Josiah A.; Myers, Thomas W.
    • The Journal of Physical Chemistry C, Vol. 120, Issue 50
    • DOI: 10.1021/acs.jpcc.6b10333

    Elemental Fluorine:  Not Only for Fluoroorganic Chemistry!
    journal, January 1996

    • Rozen, Shlomo
    • Accounts of Chemical Research, Vol. 29, Issue 5
    • DOI: 10.1021/ar950106c

    1,1′-Azobis(tetrazole): A Highly Energetic Nitrogen-Rich Compound with a N 10 Chain
    journal, April 2011

    • Klapötke, Thomas M.; Piercey, Davin G.
    • Inorganic Chemistry, Vol. 50, Issue 7
    • DOI: 10.1021/ic200071q

    Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound
    journal, September 2005

    • Huynh, My Hang V.; Hiskey, Michael A.; Chavez, David E.
    • Journal of the American Chemical Society, Vol. 127, Issue 36
    • DOI: 10.1021/ja0509735

    Nitrotetrazolate-2 N -oxides and the Strategy of N -Oxide Introduction
    journal, December 2010

    • Göbel, Michael; Karaghiosoff, Konstantin; Klapötke, Thomas M.
    • Journal of the American Chemical Society, Vol. 132, Issue 48
    • DOI: 10.1021/ja106892a

    The CN 7 Anion
    journal, January 2009

    • Klapötke, Thomas M.; Stierstorfer, Jörg
    • Journal of the American Chemical Society, Vol. 131, Issue 3
    • DOI: 10.1021/ja8077522

    Energetic Chromophores: Low-Energy Laser Initiation in Explosive Fe(II) Tetrazine Complexes
    journal, March 2016

    • Myers, Thomas W.; Bjorgaard, Josiah A.; Brown, Kathryn E.
    • Journal of the American Chemical Society, Vol. 138, Issue 13
    • DOI: 10.1021/jacs.6b02155

    Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations
    journal, January 2006

    • Byrd, Edward F. C.; Rice, Betsy M.
    • The Journal of Physical Chemistry A, Vol. 110, Issue 3
    • DOI: 10.1021/jp0536192

    Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations
    journal, May 2009

    • Byrd, Edward F. C.; Rice, Betsy M.
    • The Journal of Physical Chemistry A, Vol. 113, Issue 19
    • DOI: 10.1021/jp806520b

    Accelerating the discovery of insensitive high-energy-density materials by a materials genome approach
    journal, June 2018


    Polycyclic N -oxides: high performing, low sensitivity energetic materials
    journal, January 2019

    • Snyder, Christopher J.; Wells, Lucille A.; Chavez, David E.
    • Chemical Communications, Vol. 55, Issue 17
    • DOI: 10.1039/c8cc09653h

    Tetracyclic pyrazine-fused furazans as insensitive energetic materials: syntheses, structures, and properties
    journal, January 2018

    • Sun, Qi; Li, Xin; Lin, Qiuhan
    • Organic & Biomolecular Chemistry, Vol. 16, Issue 43
    • DOI: 10.1039/c8ob02155d

    Amino-tetrazole functionalized fused triazolo-triazine and tetrazolo-triazine energetic materials
    journal, January 2019

    • Wang, Qian; Shao, Yanli; Lu, Ming
    • Chemical Communications, Vol. 55, Issue 43
    • DOI: 10.1039/c9cc01777a

    Fused rings with N -oxide and –NH 2 : good combination for high density and low sensitivity energetic materials
    journal, January 2019

    • Hu, Lu; Yin, Ping; Imler, Gregory H.
    • Chemical Communications, Vol. 55, Issue 61
    • DOI: 10.1039/c9cc04496e

    Stabilization of an intramolecular hydrogen-bond block in an s -triazine insensitive high-energy material
    journal, January 2019

    • Li, Jie; Wang, Shucun; Liao, Longyu
    • New Journal of Chemistry, Vol. 43, Issue 27
    • DOI: 10.1039/c9nj02239b

    Multipurpose [1,2,4]triazolo[4,3- b ][1,2,4,5] tetrazine-based energetic materials
    journal, January 2019

    • Liu, Yingle; Zhao, Gang; Tang, Yongxing
    • Journal of Materials Chemistry A, Vol. 7, Issue 13
    • DOI: 10.1039/c9ta01717h

    1,2,4,5-tetrazine based energetic materials
    journal, December 1999


    Recent Advances in the Synthesis of High Explosive Materials
    journal, December 2015


    Polynitro-Functionalized Dipyrazolo-1,3,5-triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability
    journal, June 2017

    • Yin, Ping; Zhang, Jiaheng; Imler, Gregory H.
    • Angewandte Chemie International Edition, Vol. 56, Issue 30
    • DOI: 10.1002/anie.201704687

    The Chemistry and Properties of Energetic Materials Bearing [1,2,4]Triazolo[4,3- b ][1,2,4,5]tetrazine Fused Rings
    journal, October 2018

    • Wang, Guilong; Lu, Tian; Fan, Guijuan
    • Chemistry - An Asian Journal, Vol. 13, Issue 23
    • DOI: 10.1002/asia.201801145

    Comparison of 1‐Ethyl‐5 H ‐tetrazole and 1‐Azidoethyl‐5 H ‐tetrazole as Ligands in Energetic Transition Metal Complexes
    journal, April 2019

    • Wurzenberger, Maximilian H. H.; Gruhne, Michael S.; Lommel, Marcus
    • Chemistry – An Asian Journal, Vol. 14, Issue 11
    • DOI: 10.1002/asia.201900269

    Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide
    journal, October 2017

    • Tang, Yongxing; He, Chunlin; Imler, Gregory H.
    • Chemistry - A European Journal, Vol. 23, Issue 60
    • DOI: 10.1002/chem.201703930

    Simple and Efficient Synthesis of Explosive Cocrystals containing 3,5-Dimethylpyrazol-1-yl-substituted-1,2,4,5-tetrazines
    journal, October 2017

    • Snyder, Christopher J.; Chavez, David E.; Imler, Gregory H.
    • Chemistry - A European Journal, Vol. 23, Issue 65
    • DOI: 10.1002/chem.201704394

    Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine: Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine
    journal, May 2018

    • Tang, Yongxing; He, Chunlin; Yin, Ping
    • European Journal of Organic Chemistry, Vol. 2018, Issue 19
    • DOI: 10.1002/ejoc.201800347

    Synthesis and Properties of Energetic Materials Based on 1,3-Diazocyclopentane: Synthesis and Properties of Energetic Materials Based on 1,3-Diazocyclopentane
    journal, December 2018

    • Jin, Xinghui; Xiao, Menghui; Wang, Changying
    • European Journal of Organic Chemistry, Vol. 2019, Issue 5
    • DOI: 10.1002/ejoc.201801525

    An Energetic (Nitro- NNO -azoxy)triazolo-1,2,4-triazine : An Energetic (Nitro-
    journal, June 2019

    • Anikin, Oleg V.; Leonov, Nikita E.; Klenov, Michael S.
    • European Journal of Organic Chemistry, Vol. 2019, Issue 26
    • DOI: 10.1002/ejoc.201900314

    Synthesis of 4,8-Dinitraminodifurazano[3, 4- b,e ]pyrazine Derived Nitrogen-Rich Salts as Potential Energetic Materials
    journal, January 2018


    Accelerating the discovery of insensitive high-energy-density materials by a materials genome approach
    journal, June 2018


    Polycyclic N -oxides: high performing, low sensitivity energetic materials
    journal, January 2019

    • Snyder, Christopher J.; Wells, Lucille A.; Chavez, David E.
    • Chemical Communications, Vol. 55, Issue 17
    • DOI: 10.1039/c8cc09653h

    Tetracyclic pyrazine-fused furazans as insensitive energetic materials: syntheses, structures, and properties
    journal, January 2018

    • Sun, Qi; Li, Xin; Lin, Qiuhan
    • Organic & Biomolecular Chemistry, Vol. 16, Issue 43
    • DOI: 10.1039/c8ob02155d

    Amino-tetrazole functionalized fused triazolo-triazine and tetrazolo-triazine energetic materials
    journal, January 2019

    • Wang, Qian; Shao, Yanli; Lu, Ming
    • Chemical Communications, Vol. 55, Issue 43
    • DOI: 10.1039/c9cc01777a

    Fused rings with N -oxide and –NH 2 : good combination for high density and low sensitivity energetic materials
    journal, January 2019

    • Hu, Lu; Yin, Ping; Imler, Gregory H.
    • Chemical Communications, Vol. 55, Issue 61
    • DOI: 10.1039/c9cc04496e

    Stabilization of an intramolecular hydrogen-bond block in an s -triazine insensitive high-energy material
    journal, January 2019

    • Li, Jie; Wang, Shucun; Liao, Longyu
    • New Journal of Chemistry, Vol. 43, Issue 27
    • DOI: 10.1039/c9nj02239b

    Multipurpose [1,2,4]triazolo[4,3- b ][1,2,4,5] tetrazine-based energetic materials
    journal, January 2019

    • Liu, Yingle; Zhao, Gang; Tang, Yongxing
    • Journal of Materials Chemistry A, Vol. 7, Issue 13
    • DOI: 10.1039/c9ta01717h

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.