A New Correlation for Predicting the CJ Detonation Pressure of CHNO Explosives

1

PREDICTION OF HEATS OF SUBLIMATION OF ENERGETIC COMPOUNDS USING THEIR MOLECULAR STRUCTURES

Mohammad Hossein Keshavarz1, Behroz Bashavard2 , Ali Goshadro3, Zeynab Dehghan4, and Mohammad Jafari*[1]

1,2,4,5Department of Chemistry, Malek-Ashtar University of Technology, P.O. Box 83145-115, Shahin-Shahr, Islamic Republic of Iran

3Department of Chemical Engineering, Faculty of Engineering, Isfahan University, Isfahan, Islamic Republic of Iran

Table S.1.

Energetic molecules, their molecular structures and experimental sublimation enthalpies which were used in training set

Name / Molecular structure / Formula / DsubH (exp)/kJ mol-1 /
Iodotrinitromethane / / CIN3O6 / 49.0 [1]
Cyanamide / / CH2N2 / 75.2 [2]
1H-Tetrazole / / CH2N4 / 88.2 [2]
1H-Tetrazol-5-amine / / CH3N5 / 112.6 [2]
Hydrazinecarbothiohydrazide / / CH6N4S / 152.1 [2]
1,2-Dichloro-1,1,2,2-tetranitroethane / / C2Cl2N4O8 / 88.3 [1]
1-Fluoro-1,1,2,2,2-pentanitroethane / / C2FN5O10 / 69.0 [1]
2-Fluoro-2,2-dinitroethanol / / C2H3FN2O5 / 55.6 [2]
1,1,1-Trinitroethane / / C2H3N3O6 / 72.0 [2]
1,3-Dinitro-1,3-diazacyclobutane / / C2H4N4O4 / 94.2 [3]
1,1-Diamino-2,2-dinitroethene (FOX-7) / / C2H4N4O4 / 108.7 [4]
2-Methyl-1H-tetrazol-5-amine / / C2H5N5 / 90.6 [2]
1,3-Dichloro-1,1,3,3-tetranitropropane / / C3H2Cl2N4O8 / 93.7 [1]
2-Methyl-4-nitro-1,2,3-triazole / / C3H4N4O2 / 74.7 [2]
2,4-Dinitro-2,4-diazapentane / / C3H8N4O4 / 108.8 [5]
Fumaronitrile / / C4H2N2 / 68.6 [2]
2-Nitrofuran / / C4H3NO3 / 75.3 [2]
N,N-Bis (2,2,2-trinitroethyl) nitramide / / C4H4N8O14 / 117.6 [2]
1-Fluoro-1,1,3,3-tetranitrobutane / / C4H5FN4O8 / 91.6 [1]
1-Iodo-1,1,3,3-tetranitrobutane / / C4H5IN4O8 / 99.2 [1]
1,1,3,3-Tetranitrobutane / / C4H6N4O8 / 87.9 [2]
2,2,3,3-Tetranitrobutane / / C4H6N4O8 / 78.2 [2]
2-Methyl-1,1,1,3-tetranitropropane / / C4H6N4O8 / 91.2 [2]
1,3,5,7-Tetranitro-1,3,5,7-tetrazocane (HMX) / / C4H8N8O8 / 161.0 [6]
2,4,6-Trinitropyridine / / C5H2N4O6 / 101.7 [2]
2,4,6-Trinitropyridine 1-oxide / / C5H2N4O7 / 106.3 [2]
5-Nitrofuran-2-carbaldehyde / / C5H3NO4 / 75.3 [1]
Benzotrifuroxan / / C6N6O6 / 172.5 [2]
2-Chloro-1,3,5-trinitrobenzene / / C6H2ClN3O6 / 103.8 [2]
1,2-Dichloro-4-nitrobenzene / / C6H3Cl2NO2 / 85.8 [2]
1,3-Dichloro-5-nitrobenzene / / C6H3Cl2NO2 / 83.2 [2]
1,4-Dichloro-2-nitrobenzene / / C6H3Cl2NO2 / 87.4 [2]
1,4-Dibromo-2-nitrobenzene / / C6H3Br2NO2 / 97.0 [2]
4-Nitrobenzofurazan-1-oxide / / C6H3N3O4 / 97.3 [2]
2,4,6-Trinitro-1,3-benzenediol (TNR) / / C6H3N3O8 / 120.8 [6]
1-Chloro-3-nitrobenzene / / C6H4ClNO2 / 82.5 [2]
1-Chloro-4-nitrobenzene / / C6H4ClNO2 / 74.7 [2]
1-Bromo-2-nitrobenzene / / C6H4BrNO2 / 85.2 [2]
1-Bromo-3-nitrobenzene / / C6H4BrNO2 / 86.8 [2]
1-Iodo-3-nitrobenzene / / C6H4INO2 / 83.2 [2]
4-Chloro-3-nitrophenol / / C6H4ClNO3 / 111.0 [2]
2,5-Dichloro-4-nitroaniline / / C6H4Cl2N2O2 / 114.3 [2]
2,6-Dichloro-4-nitroaniline / / C6H4Cl2N2O2 / 109.2 [2]
4,5-Dichloro-2-nitroaniline / / C6H4Cl2N2O2 / 109.4 [2]
1,2-Dinitrobenzene / / C6H4N2O4 / 95.5 [2]
1,4-Dinitrobenzene / / C6H4N2O4 / 94.3 [2]
2,4-Dinitrophenol / / C6H4N2O5 / 104.6 [1]
2,6-Dinitrophenol / / C6H4N2O5 / 112.1 [1]
3,4-Dinitrophenol / / C6H4N2O5 / 123.5 [1]
4-Chloro-2,6-dinitroaniline / / C6H4ClN3O4 / 105.2 [2]
2,4,6-Trinitroaniline (TNA) / / C6H4N4O6 / 125.3 [6]
2-Nitrobenzene-1,3-diol / / C6H5NO4 / 74.5 [2]
2-Chloro-4-nitroaniline / / C6H5ClN2O2 / 102.6 [2]
2-Chloro-5-nitroaniline / / C6H5ClN2O2 / 101.0 [2]
1,3-Diamino-2,4,6-trinitrobenzene (DATB) / / C6H5N5O6 / 143.5 [6]
3-Methyl-4-nitropyridine 1-oxide / / C6H6N2O3 / 106.7 [2]
2,4,6-Trinitrobenzene-1,3,5-triamine (TATB) / / C6H6N6O6 / 168.2 [2]
N,N-Bis (2,2-dinitropropyl) nitrous amide / / C6H10N6O9 / 110.9 [2]
Trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecaline (TNAD) / / C6H10N8O8 / 154.2 [3]
2-Methyl-2,3,3-trinitropentane / / C6H11N3O6 / 90.8 [2]
3,3,6,6-Tetramethyl-1,2,4,5-tetraoxane (DADP) / / C6H12O4 / 81.9 [7]
2,3-Dimethyl-2,3-dinitrobutane / / C6H12N2O4 / 79.5 [2]
2,4,6-Trinitrobenzoic acid / / C7H3N3O8 / 154.7 [3]
2-Nitrobenzonitrile / / C7H4N2O2 / 88.1 [2]
3,4-Dinitrobenzoic acid / / C7H4N2O6 / 129.0 [2]
3-Nitrobenzoic acid / / C7H5NO4 / 110.0 [2]
4-Nitrobenzoic acid / / C7H5NO4 / 119.7 [2]
3-(5-nitro-2-furyl)-2-propenal / / C7H5NO4 / 97.9 [2]
3-Methyl-2,4,6-trinitrophenol / / C7H5N3O7 / 111.2 [6]
2,4,6-N-Tetranitro-N-methylaniline (Tetryl) / / C7H5N5O8 / 133.8 [6]
1-(Chloromethyl)-2-nitrobenzene / / C7H6ClNO2 / 96.2 [2]
1-Methyl-2,3-dinitrobenzene / / C7H6N2O4 / 97.0 [2]
2-Methyl-1,3-dinitrobenzene / / C7H6N2O4 / 98.3 [2]
2-Methyl-3,5-dinitrophenol / / C7H6N2O5 / 103.3 [2]
2-Methoxy-4-nitrophenol / / C7H7NO4 / 99.4 [2]
2-Methoxy-5-nitrophenol / / C7H7NO4 / 106.2 [2]
4-Methoxy-2-nitrophenol / / C7H7NO4 / 90.8 [2]
2,2-Dimethyl-1,1,1,4,4-pentanitropentane / / C7H11N5O10 / 103.8 [2]
5-Nitro-1H-indole / / C8H6N2O2 / 110.5 [2]
1-(3-Nitrophenyl) ethan-1-one / / C8H7NO3 / 110.0 [2]
2-Methyl-3-nitrobenzoic acid / / C8H7NO4 / 119.5 [2]
2-Methyl-6-nitrobenzoic acid / / C8H7NO4 / 120.0 [2]
3-Methoxy-2-nitrobenzoic acid / / C8H7NO5 / 141.9 [2]
3-Methoxy-4-nitrobenzoic acid / / C8H7NO5 / 131.0 [2]
2,4-Dimethyl-1,3,5-trinitrobenzene (TNX) / / C8H7N3O6 / 129.8 [6]
(2,2,2-Trinitroethyl) benzene / / C8H7N3O6 / 84.1 [2]
N,N-Dimethyl-3-nitroaniline / / C8H10N2O2 / 92.7 [2]
N,N-Dimethyl-4-nitroaniline / / C8H10N2O2 / 102.7 [2]
2,5-Dimethyl hexane-2,5-dihydroperoxide / / C8H18O4 / 138.6 [1]
5-Nitroquinoline / / C9H6N2O2 / 94.2 [2]
6-Nitroquinoline / / C9H6N2O2 / 103.8 [2]
5-Nitro-8-hydroxyquinoline / / C9H6N2O3 / 86.1 [2]
6-Nitroquinolin-5-amine / / C9H7N3O2 / 136.4 [2]
2,4,6-Trimethyl-1,3,5-trinitrobenzene / / C9H9N3O6 / 103.6 [6]
N,N-Dimethyl-4-nitrobenzamide / / C9H10N2O3 / 115.0 [1]
1-(3-Nitrophenyl)-1H-pyrrole-2,5-dione / / C10H6N2O4 / 117.3 [2]
2-Methyl-8-nitroquinoline / / C10H8N2O2 / 111.0 [2]
1-Nitroadamantane / / C10H15NO2 / 63.6 [2]
2-Nitroadamantane / / C10H15NO2 / 58.0 [2]
(E)-4-((4-Nitrophenyl)amino)pent-3-en-2-one / / C11H12N2O3 / 121.9 [2]
(E)-2-Methyl-N-(4-nitrobenzylidene)propan-2-amine / / C11H14N2O2 / 91.1 [2]
(E)-N-tert-Butyl-1-(4-nitrophenyl)methanimine oxide / / C11H14N2O3 / 116.5 [2]
1-Nitro-4-(3-nitropentan-3-yl) benzene / / C11H14N2O4 / 110.8 [2]
2,2',4,4',6,6'-Hexanitro-1,1'-biphenyl / / C12H4N6O12 / 171.8 [3]
Bis (2,4,6-trinitrophenyl) sulfane / / C12H4N6O12S / 173.4 [3]
5,7-Dinitro-1-(2,4,6-trinitrophenyl)-1H-benzo[d][1,2,3]triazole / / C12H4N8O10 / 179.7 [3]
4,4'-Dinitro-1,1'-biphenyl / / C12H8N2O4 / 104.6 [2]
4-Hydroxy-4'-nitroazobenzene / / C12H9N3O3 / 136.8 [2]
4-((2,4-Dinitrophenyl)amino) phenol / / C12H9N3O5 / 155.6 [2]
N-(2-Nitrophenyl)-N-phenylamine / / C12H10N2O2 / 101.9 [2]
N-(4-Nitrophenyl)-N-phenylamine / / C12H10N2O2 / 126.2 [2]
1-(tert-Butyl)-2-methoxy-4-methyl-3,5-dinitrobenzene / / C12H16N2O5 / 102.9 [2]
N-Phenyl 4-nitrobenzaldehyde imine / / C13H10N2O2 / 126.0 [2]
1-Amino-5,8-dichloro-4-nitroanthracene-9,10-dione / / C14H6Cl2N2O4 / 158.2 [2]
2,2',4,4',6,6'-Hexanitrostilbene (HNS) / / C14H6N6O12 / 171.6 [3]
1-Nitroanthracene-9,10-dione / / C14H7NO4 / 108.9 [2]
3,3'-Dimethyl-2,2',4,4',6,6'-hexanitro-1,1'-biphenyl / / C14H8N6O12 / 160.8 [3]
Benzoic peroxyanhydride (or Benzoyl peroxide) / / C14H10O4 / 97.9 [2]
3-Nitro-4'-(N,N-dimethylamino)-azobenzene / / C14H14N4O2 / 133.9 [2]
4-Nitro-4'-(N,N-dimethylamino)-azobenzene / / C14H14N4O2 / 134.3 [2]
4-(N,N-Dimethylamino)azobenzene / / C14H15N3 / 117.6 [2]
3-Methyl-3'-nitro-4,N,N-dimethylaminoazobenzene / / C15H16N4O2 / 101.7 [2]
4-(N-Ethyl-N-2-hydroxyethylamino)-4'-nitro-2'-chloroazobenzene / / C16H17ClN4O3 / 142.7 [2]
4-(N-Ethyl-N-2-hydroxyethylamino)-4'-nitroazobenzene / / C16H18N4O3 / 136.8 [2]
2,4,6-Tri-tert-butylnitrobenzene / / C18H29NO2 / 96.4 [2]

Table S.2.

Energetic molecules, their molecular structures and experimental sublimation enthalpies which were used in validation set

Name / Molecular structure / Formula / DsubH (exp)/kJ mol-1 /
Trinitromethane / / CHN3O6 / 45.2 [2]
Methyldinitramine / / CH3N3O4 / 52.0 [1]
Nitroguanidine (NQ) / / CH4N4O2 / 142.7 [6]
Hexanitroethane / / C2N6O12 / 70.7 [2]
1H-1,2,4-triazole / / C2H3N3 / 80.7 [2]
1-Methyl-1H-tetrazol-5-amine / / C2H5N5 / 116.4 [2]
N,N-Dimethylnitramide / / C2H6N2O2 / 41.4 [1]
1,3-Diiodo-1,1,3,3-tetranitropropane / / C3H2I2N4O8 / 111.0 [1]
1,1,1,2,2-Pentanitropropane / / C3H3N5O10 / 77.4 [2]
1,3,3-Trinitroazetidine (TNAZ) / / C3H4N4O6 / 106.2 [3]
1,3,5-Trinitroso-1,3,5-triazinane (TTT) / / C3H6N6O3 / 112.1 [2]
1,3,5-Trinitro-1,3,5-triazinane (RDX) / / C3H6N6O6 / 134.3 [6]
1-Chloro-1,1,3,3-tetranitrobutane / / C4H5ClN4O8 / 91.6 [1]
Bis (2,2,2-trinitroethyl) amine / / C4H5N7O12 / 80.8 [2]
1,1,1,4-Tetranitrobutane / / C4H6N4O8 / 99.6 [2]
4-Nitromorpholine / / C4H8N2O3 / 81.6 [1]
1,4-Dinitropiperazine / / C4H8N4O4 / 111.3 [2]
1,1,1,3,5,5,5-Heptanitropentane / / C5H5N7O14 / 111.7 [2]
3,5-Dimethyl-4-nitrosopyrazole / / C5H7N3O / 102.9 [2]
Pentaerythritol Tetranitrate (PETN) / / C5H8N4O12 / 150.4 [6]
2,4-Dichloro-1-nitrobenzene / / C6H3Cl2NO2 / 87.8 [2]
1,3,5-Trinitrobenzene (TNB) / / C6H3N3O6 / 107.3 [6]
2,4,6-Trinitrophenol (Picric acid) / / C6H3N3O7 / 105.1 [6]
1-Chloro-2-nitrobenzene / / C6H4ClNO2 / 80.9 [2]
1-Bromo-4-nitrobenzene / / C6H4BrNO2 / 86.6 [2]
4-Chloro-2-nitrophenol / / C6H4ClNO3 / 87.6 [2]
1,3-Dinitrobenzene / / C6H4N2O4 / 87.0 [2]
2,3-Dinitrophenol / / C6H4N2O5 / 96.6 [1]
2,5-Dinitrophenol / / C6H4N2O5 / 93.4 [1]
2-Chloro-4,6-dinitroaniline / / C6H4ClN3O4 / 115.0 [2]
1-Azido-4-nitrobenzene / / C6H4N4O2 / 81.0 [1]
2-Nitrophenol / / C6H5NO3 / 73.3 [2]
3-Nitrophenol / / C6H5NO3 / 91.2 [2]
4-Nitrophenol / / C6H5NO3 / 92.4 [2]
4-Nitrobenzene-1,2-diol / / C6H5NO4 / 121.1 [1]
Methyl 5-nitrofuran-2-carboxylate / / C6H5NO5 / 104.2 [2]
2-Nitroaniline / / C6H6N2O2 / 89.0 [2]
3-Nitroaniline / / C6H6N2O2 / 96.5 [2]
4-Nitroaniline / / C6H6N2O2 / 101.4 [2]
(2,4-Dinitrophenyl) hydrazine / / C6H6N4O4 / 124.3 [8]
4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX) / / C6H6N4O8 / 123.4 [3]
2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20) / / C6H6N12O12 / 168.7 [3]
N,N-Bis (2,2-dinitropropyl) nitramide / / C6H10N6O10 / 99.2 [2]
Bis (2,2-dinitropropyl) amine / / C6H11N5O8 / 105.4 [2]
Hexamethylene triperoxide diamine (HMTD) / / C6H12N2O6 / 76.2 [9]
3-Nitrobenzonitrile / / C7H4N2O2 / 92.8 [2]
4-Nitrobenzonitrile / / C7H4N2O2 / 91.1 [2]
2,4-Dinitrobenzoic acid / / C7H4N2O6 / 135.0 [2]
2-Nitrobenzoic acid / / C7H5NO4 / 118.7 [2]
5-Nitro-1,3-benzodioxole / / C7H5NO4 / 97.4 [2]
2-Methyl-1,3,5-trinitrobenzene (TNT) / / C7H5N3O6 / 113.2 [6]
2-Methoxy-1,3,5-trinitrobenzene / / C7H5N3O7 / 111.2 [6]
(Dinitromethyl) benzene / / C7H6N2O4 / 76.1 [2]
1-Methyl-2,4-dinitrobenzene / / C7H6N2O4 / 99.6 [2]
4-Methyl-1,2-dinitrobenzene / / C7H6N2O4 / 99.6 [2]
1-Methyl-4-nitrobenzene / / C7H7NO2 / 74.8 [2]
Tris (2,2,2-trinitroethoxy) methane / / C7H7N9O21 / 150.0 [1]
2-(2-Nitrophenyl) acetyl chloride / / C8H6ClNO3 / 103.6 [2]
2-(3-Nitrophenyl) acetyl chloride / / C8H6ClNO3 / 109.1 [2]
2-Chloro-1-phenylethan-1-one / / C8H7ClO / 90.7 [2]
2,3-Dihydro-6-nitro-1,4-benzodioxin / / C8H7NO4 / 100.6 [2]
3-Methyl-2-nitrobenzoic acid / / C8H7NO4 / 124.4 [2]
3-Methyl-4-nitrobenzoic acid / / C8H7NO4 / 119.3 [2]
4-Methyl-3-nitrobenzoic acid / / C8H7NO4 / 118.6 [2]
4-Methoxy-3-nitrobenzoic acid / / C8H7NO5 / 131.2 [2]
2-Ethoxy-1,3,5-trinitrobenzene / / C8H7N3O7 / 120.5 [2]
5-Nitroindoline / / C8H8N2O2 / 109.8 [2]
8-Nitroquinoline / / C9H6N2O2 / 106.7 [2]
(5-Nitrofuran-2-yl) methylene diacetate / / C9H9NO7 / 126.0 [1]
2,4,6-Trimethyl nitrobenzene / / C9H11NO2 / 78.6 [2]
3,3,6,6,9,9-Hexamethyl-1,2,4,5,7,8-hexaoxonane / / C9H18O6 / 72.5 [7]
1-Nitronaphthalene / / C10H7NO2 / 95.1 [2]
2,2-Dinitroadamantane / / C10H14N2O4 / 96.4 [2]
2-Nitroadamantane-2-carbonitrile / / C11H14N2O2 / 70.0 [1]
Bis(2,4,6-trinitrophenyl)amine (Hexyl) / / C12H5N7O12 / 171.6 [3]
4-Nitroazobenzene / / C12H9N3O2 / 110.0 [2]
2,4-Dinitro-N-phenylaniline / / C12H9N3O4 / 147.6 [2]
4-Amino-4'-nitroazobenzene / / C12H10N4O2 / 123.0 [2]
1-(tert-Butyl)-3,5-dimethyl-2,4,6-trinitrobenzene / / C12H15N3O6 / 100.4 [2]
2-Nitrofluorene / / C13H9NO2 / 114.2 [2]
4'-Nitro-2-methylaminoazobenzene / / C13H12N4O2 / 134.7 [2]
1,4-Dinitroanthracene-9,10-dione / / C14H6N2O6 / 131.0 [2]
9-Nitroanthracene / / C14H9NO2 / 115.4 [2]
Benzoic (cyclohexyl carbonic) peroxyanhydride / / C14H16O5 / 96.2 [2]
1-(4-(tert-Butyl)-2,6-dimethyl-3,5-dinitrophenyl)ethanone / / C14H18N2O5 / 107.9 [2]
N-[4-[(2-Hydroxy-5-methylphenyl)azo]phenyl] acetamide (Disperse yellow 3) / / C15H15N3O2 / 140.6 [1]
4-(N,N-Diethylamino)-4'-nitroazobenzene / / C16H18N4O2 / 151.5 [2]
(Peroxybis (methanetetrayl)) hexabenzene / / C38H30O2 / 158.1 [2]

References

1. Linstrom PJ, Mallard WG. NIST Chemistry WebBook, NIST Standard Reference Database Number 69, Available at: http://webbook.nist.gov. 2014.

2. Acree W, Chickos JS. Phase Transition Enthalpy Measurementsof Organic and Organometallic Compounds. Sublimation, Vaporizationand Fusion Enthalpies From 1880 to 2010. J Phys Chem Ref Data. 2010;39(4):1-942. doi:10.1063/1.3309507.

3. Zeman S, Krupka M. New aspects of impact reactivity of polynitro compounds, Part III. Impact sensitivity as a function of the imtermolecular interactions. Propellants, Explos, Pyrotech. 2003;28(6):301-7. doi:10.1002/prep.200300018.

4. Hu A, Larade B, Dudiy S, Abou-Rachid H, Lussier L-S, Guo H. Theoretical Prediction of Heats of Sublimation of Energetic Materials Using Pseudo-Atomic Orbital Density Functional Theory Calculations. Propellants, Explos, Pyrotech. 2007;32(4):331-7.

5. Arnautova EA, Zakharova MV, Pivina TS, Smolenskii EA, Sukhachev DV, Shcherbukhin VV. Methods for calculating the enthalpies of sublimation of organic molecular crystals. Russian chemical bulletin. 1996;45(12):2723-32.

6. Cundall RB, Palmer TF, Wood CE. Vapour pressure measurements on some organic high explosives. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases. 1978;74:1339-45.

7. Matyas R, Pachman J. Primary Explosives. New York: Springer-Verlag Berlin Heidelberg; 2013.

8. Behrens R, Wiese-Smith D, Johnston L, Maharrey S. Evaluation of Ingredients for the Development of New Insensitive Munitions, SAND2004-5309. Albuquerque, New Mexico: Sandia National Laboratories2004.

9. Burks RM, Hage DS. Current trends in the detection of peroxide-based explosives. Anal Bioanal Chem. 2009;395(2):301-13.

[1] Author for correspondence: