Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound
The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C−N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NΔH f), experimentally determined using an additive method, is shown to be the highest positive NΔH f...
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| Published in: | Journal of the American Chemical Society Vol. 127; no. 36; pp. 12537 - 12543 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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Washington, DC
American Chemical Society
14-09-2005
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| Abstract | The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C−N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NΔH f), experimentally determined using an additive method, is shown to be the highest positive NΔH f compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C−N compounds, for example, 2,4,6-triazido-1,3,5-triazine; 4,4‘,6,6‘-tetra(azido)hydrazo-1,3,5-triazine; 4,4‘,6,6‘-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3,4,6,7,9,9b-heptaazaphenalene (heptazine). |
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| AbstractList | The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NDeltaHf), experimentally determined using an additive method, is shown to be the highest positive NDeltaHf compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds, for example, 2,4,6-triazido-1,3,5-triazine; 4,4',6,6'-tetra(azido)hydrazo-1,3,5-triazine; 4,4',6,6'-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3,4,6,7,9,9b-heptaazaphenalene (heptazine). The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C−N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NΔH f), experimentally determined using an additive method, is shown to be the highest positive NΔH f compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C−N compounds, for example, 2,4,6-triazido-1,3,5-triazine; 4,4‘,6,6‘-tetra(azido)hydrazo-1,3,5-triazine; 4,4‘,6,6‘-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3,4,6,7,9,9b-heptaazaphenalene (heptazine). |
| Author | Chavez, David E Gilardi, Richard D Huynh, My Hang V Hiskey, Michael A Naud, Darren L |
| Author_xml | – sequence: 1 givenname: My Hang V surname: Huynh fullname: Huynh, My Hang V – sequence: 2 givenname: Michael A surname: Hiskey fullname: Hiskey, Michael A – sequence: 3 givenname: David E surname: Chavez fullname: Chavez, David E – sequence: 4 givenname: Darren L surname: Naud fullname: Naud, Darren L – sequence: 5 givenname: Richard D surname: Gilardi fullname: Gilardi, Richard D |
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| Cites_doi | 10.1002/jhet.5570280844 10.1002/anie.200453867 10.1002/jhet.5570350616 10.1007/s00339-004-2821-9 10.1023/A:1026072221020 10.1002/prep.200300001 10.1002/anie.200352680 10.1063/1.1743193 10.1107/S0365110X5500159X 10.1002/anie.200453868 10.1021/cen-v082n041.p044 10.1002/(SICI)1521-3773(20000515)39:10<1791::AID-ANIE1791>3.0.CO;2-9 10.1002/1521-4087(200206)27:3<111::AID-PREP111>3.0.CO;2-O 10.1021/cm000570y 10.1021/jo01044a053 10.1021/cen-v082n039.p035 10.1016/S0011-2275(03)00051-1 10.1021/cen-v082n044.p024 10.1002/anie.200461765 10.1086/480220 10.1002/prep.200300003 |
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| References | Hammerl A. (ja0509735b00034/ja0509735b00034_1) 2003; 28 Wilson E. K. (ja0509735b00027/ja0509735b00027_1) 2004; 82 Son S. F. (ja0509735b00018/ja0509735b00018_1) 2000; 28 Pervozvanskaya M. A. (ja0509735b00031/ja0509735b00031_1) 1975; 11 Huynh M. H. V. (ja0509735b00008/ja0509735b00008_1) 2004; 22 Haiges R. (ja0509735b00045/ja0509735b00045_1) 2003; 42 Miller D. R. (ja0509735b00016/ja0509735b00016_1) 2004; 126 Freudenberger J. (ja0509735b00035/ja0509735b00035_1) 2003; 43 Kerth J. (ja0509735b00004/ja0509735b00004_1) 2002; 27 Ritter S. (ja0509735b00012/ja0509735b00012_1) 2004; 82 Fallis S. (ja0509735b00023/ja0509735b00023_1) Briggs P. R. (ja0509735b00028/ja0509735b00028_1) 1968; 13 ja0509735b00038/ja0509735b00038_1 Raj B. (ja0509735b00036/ja0509735b00036_1) 2002; 55 Gillan E. G. (ja0509735b00014/ja0509735b00014_1) 2000; 12 Coburn M. D. (ja0509735b00040/ja0509735b00040_1) 1991; 28 Licht H.-H. (ja0509735b00044/ja0509735b00044_1) 1994; 12 Latosh N. I. (ja0509735b00042/ja0509735b00042_1) 1970; 35 Williams G. K. (ja0509735b00029/ja0509735b00029_1) 1994; 98 Bertinotti F. (ja0509735b00032/ja0509735b00032_1) 1955; 8 Benson F. R. (ja0509735b00002/ja0509735b00002_1) 1984 Chavez D. E. (ja0509735b00003/ja0509735b00003_1) 2000; 39 Ali A. N. (ja0509735b00017/ja0509735b00017_1) 2004; 20 Kessenich E. (ja0509735b00046/ja0509735b00046_1) 1998; 12 Chavez D. E. (ja0509735b00041/ja0509735b00041_1) 1998; 35 Sato T. (ja0509735b00015/ja0509735b00015_1) 2004; 79 Huynh M. H. V. (ja0509735b00005/ja0509735b00005_1) 2004; 43 Chavez D. E. (ja0509735b00020/ja0509735b00020_1) 1999; 10 Tartakovsky V. A. (ja0509735b00010/ja0509735b00010_1) 1996; 418 Huynh M. H. V. (ja0509735b00013/ja0509735b00013_1) 2005; 44 Paine R. T. (ja0509735b00039/ja0509735b00039_1) 1999; 38 Zhou G. (ja0509735b00006/ja0509735b00006_1) 2004; 668 Huynh M. H. V. (ja0509735b00043/ja0509735b00043_1) 2004; 43 Kofman T. P. (ja0509735b00030/ja0509735b00030_1) 2003; 39 Churakov A. M. (ja0509735b00009/ja0509735b00009_1) 2002; 14 Marcus J. H. (ja0509735b00037/ja0509735b00037_1) 1963; 28 Bennett G. (ja0509735b00022/ja0509735b00022_1) 2003 Boitsov E. N. (ja0509735b00025/ja0509735b00025_1) 1962; 32 Finkelshtein A. I. (ja0509735b00026/ja0509735b00026_1) 1964; 33 Neutz J. (ja0509735b00007/ja0509735b00007_1) 2003; 28 Ritter S. (ja0509735b00001/ja0509735b00001_1) 2004; 82 Ott E. (ja0509735b00024/ja0509735b00024_1) 1921; 54 Huynh M. H. V. (ja0509735b00011/ja0509735b00011_1) 2004; 43 Jadhav H. S. (ja0509735b00019/ja0509735b00019_1) 2001; 4 Chavez D. E. (ja0509735b00021/ja0509735b00021_1) 1998; 7 Paoloni L. (ja0509735b00033/ja0509735b00033_1) 1956; 25 |
| References_xml | – volume: 28 start-page: 2050 year: 1991 ident: ja0509735b00040/ja0509735b00040_1 publication-title: J. Heterocycl. Chem. doi: 10.1002/jhet.5570280844 contributor: fullname: Coburn M. D. – volume: 43 start-page: 5661 year: 2004 ident: ja0509735b00011/ja0509735b00011_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200453867 contributor: fullname: Huynh M. H. V. – volume: 35 start-page: 1332 year: 1998 ident: ja0509735b00041/ja0509735b00041_1 publication-title: J. Heterocycl. Chem. doi: 10.1002/jhet.5570350616 contributor: fullname: Chavez D. E. – volume: 35 start-page: 1371 year: 1970 ident: ja0509735b00042/ja0509735b00042_1 publication-title: Russ. J. Org. Chem. contributor: fullname: Latosh N. I. – volume: 12 start-page: 2016 year: 1998 ident: ja0509735b00046/ja0509735b00046_1 publication-title: Eur. J. Inorg. Chem. contributor: fullname: Kessenich E. – volume: 79 start-page: 1479 year: 2004 ident: ja0509735b00015/ja0509735b00015_1 publication-title: Appl. Phys. A doi: 10.1007/s00339-004-2821-9 contributor: fullname: Sato T. – volume: 39 start-page: 584 year: 2003 ident: ja0509735b00030/ja0509735b00030_1 publication-title: Russ. J. Org. Chem. doi: 10.1023/A:1026072221020 contributor: fullname: Kofman T. P. – volume-title: Military Aerospace Technology year: 2003 ident: ja0509735b00022/ja0509735b00022_1 contributor: fullname: Bennett G. – volume: 7 start-page: 14 year: 1998 ident: ja0509735b00021/ja0509735b00021_1 publication-title: J. Pyrotech. contributor: fullname: Chavez D. E. – volume: 28 start-page: 173 year: 2003 ident: ja0509735b00034/ja0509735b00034_1 publication-title: Propellants, Explos., Pyrotech. doi: 10.1002/prep.200300001 contributor: fullname: Hammerl A. – volume: 42 start-page: 5851 year: 2003 ident: ja0509735b00045/ja0509735b00045_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200352680 contributor: fullname: Haiges R. – volume: 20 start-page: 126 year: 2004 ident: ja0509735b00017/ja0509735b00017_1 publication-title: J. Propul. Power contributor: fullname: Ali A. N. – volume: 25 start-page: 1277 year: 1956 ident: ja0509735b00033/ja0509735b00033_1 publication-title: J. Chem. Phys. doi: 10.1063/1.1743193 contributor: fullname: Paoloni L. – volume: 8 start-page: 514 year: 1955 ident: ja0509735b00032/ja0509735b00032_1 publication-title: Acta Crystallogr. doi: 10.1107/S0365110X5500159X contributor: fullname: Bertinotti F. – volume: 668 start-page: 195 year: 2004 ident: ja0509735b00006/ja0509735b00006_1 publication-title: J. Mol. Struct. Theochem. contributor: fullname: Zhou G. – volume: 43 start-page: 4928 year: 2004 ident: ja0509735b00043/ja0509735b00043_1 publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200453868 contributor: fullname: Huynh M. H. V. – volume: 4 start-page: 504 year: 2001 ident: ja0509735b00019/ja0509735b00019_1 publication-title: Theory Pract. Energ. Mater. contributor: fullname: Jadhav H. S. – volume: 82 start-page: 44 issue: 41 year: 2004 ident: ja0509735b00001/ja0509735b00001_1 publication-title: Chem. Eng. News doi: 10.1021/cen-v082n041.p044 contributor: fullname: Ritter S. – volume: 39 start-page: 1793 year: 2000 ident: ja0509735b00003/ja0509735b00003_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/(SICI)1521-3773(20000515)39:10<1791::AID-ANIE1791>3.0.CO;2-9 contributor: fullname: Chavez D. E. – volume: 54 start-page: 186 year: 1921 ident: ja0509735b00024/ja0509735b00024_1 publication-title: Ber. Dtsch. Chem. Ges. contributor: fullname: Ott E. – volume: 22 start-page: 229 year: 2004 ident: ja0509735b00008/ja0509735b00008_1 publication-title: J. Energ. Mater. contributor: fullname: Huynh M. H. V. – volume: 27 start-page: 118 year: 2002 ident: ja0509735b00004/ja0509735b00004_1 publication-title: Propellants, Explos., Pyrotech. doi: 10.1002/1521-4087(200206)27:3<111::AID-PREP111>3.0.CO;2-O contributor: fullname: Kerth J. – volume: 12 start-page: 235 year: 1994 ident: ja0509735b00044/ja0509735b00044_1 publication-title: J. Energ. Mater. contributor: fullname: Licht H.-H. – volume: 12 start-page: 3912 year: 2000 ident: ja0509735b00014/ja0509735b00014_1 publication-title: Chem. Mater. doi: 10.1021/cm000570y contributor: fullname: Gillan E. G. – volume-title: Proceedings of Halon Options Technical Working Conference ident: ja0509735b00023/ja0509735b00023_1 contributor: fullname: Fallis S. – volume: 98 start-page: 204 year: 1994 ident: ja0509735b00029/ja0509735b00029_1 publication-title: Combust. Flame contributor: fullname: Williams G. K. – volume: 28 start-page: 2375 year: 1963 ident: ja0509735b00037/ja0509735b00037_1 publication-title: J. Org. Chem. doi: 10.1021/jo01044a053 contributor: fullname: Marcus J. H. – volume: 33 start-page: 405 year: 1964 ident: ja0509735b00026/ja0509735b00026_1 publication-title: Russ. Chem. Rev. contributor: fullname: Finkelshtein A. I. – volume: 418 start-page: 24 year: 1996 ident: ja0509735b00010/ja0509735b00010_1 publication-title: Mater. Res. Soc. Sym. Proc. contributor: fullname: Tartakovsky V. A. – volume: 82 start-page: 35 issue: 22 year: 2004 ident: ja0509735b00027/ja0509735b00027_1 publication-title: Chem. Eng. News doi: 10.1021/cen-v082n039.p035 contributor: fullname: Wilson E. K. – volume: 43 start-page: 136 year: 2003 ident: ja0509735b00035/ja0509735b00035_1 publication-title: Cryogenics doi: 10.1016/S0011-2275(03)00051-1 contributor: fullname: Freudenberger J. – volume: 55 start-page: 147 year: 2002 ident: ja0509735b00036/ja0509735b00036_1 publication-title: Trans. Indian Inst. Met. contributor: fullname: Raj B. – volume: 13 start-page: 728 year: 1968 ident: ja0509735b00028/ja0509735b00028_1 publication-title: Chem. Commun. contributor: fullname: Briggs P. R. – volume: 126 start-page: 5373 year: 2004 ident: ja0509735b00016/ja0509735b00016_1 publication-title: J. Am. Chem. Soc. contributor: fullname: Miller D. R. – volume: 82 start-page: 24 issue: 44 year: 2004 ident: ja0509735b00012/ja0509735b00012_1 publication-title: Chem. Eng. News doi: 10.1021/cen-v082n044.p024 contributor: fullname: Ritter S. – volume: 44 start-page: 739 year: 2005 ident: ja0509735b00013/ja0509735b00013_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200461765 contributor: fullname: Huynh M. H. V. – volume: 32 start-page: 3339 year: 1962 ident: ja0509735b00025/ja0509735b00025_1 publication-title: J. Gen. Chem. contributor: fullname: Boitsov E. N. – volume: 11 start-page: 1976 year: 1975 ident: ja0509735b00031/ja0509735b00031_1 publication-title: Zh. Org. Khim. contributor: fullname: Pervozvanskaya M. A. – volume: 38 start-page: 3743 year: 1999 ident: ja0509735b00039/ja0509735b00039_1 publication-title: Inorg. Chem. contributor: fullname: Paine R. T. – volume: 14 start-page: 2349 year: 2002 ident: ja0509735b00009/ja0509735b00009_1 publication-title: Eur. J. Org. Chem. contributor: fullname: Churakov A. M. – volume: 43 start-page: 4928 year: 2004 ident: ja0509735b00005/ja0509735b00005_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200453868 contributor: fullname: Huynh M. H. V. – volume: 10 start-page: 36 year: 1999 ident: ja0509735b00020/ja0509735b00020_1 publication-title: J. Pyrotech. contributor: fullname: Chavez D. E. – volume-title: The High-Nitrogen Compounds year: 1984 ident: ja0509735b00002/ja0509735b00002_1 contributor: fullname: Benson F. R. – ident: ja0509735b00038/ja0509735b00038_1 doi: 10.1086/480220 – volume: 28 start-page: 188 year: 2003 ident: ja0509735b00007/ja0509735b00007_1 publication-title: Propellants, Explos., Pyrotech. doi: 10.1002/prep.200300003 contributor: fullname: Neutz J. – volume: 28 start-page: 924 year: 2000 ident: ja0509735b00018/ja0509735b00018_1 publication-title: Proc. Combust. Inst. contributor: fullname: Son S. F. |
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| Snippet | The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C−N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are... The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are... |
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| SubjectTerms | Azides - chemical synthesis Azides - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Heterocyclic Compounds, 3-Ring - chemistry Models, Molecular Molecular Structure Nitrogen - chemistry Organic chemistry Preparations and properties Thermodynamics Triazines |
| Title | Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound |
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