Computational Studies on Energetic Performance of Polynitro-substituted Uric Acid Derivatives

doi:10.7503/cjcu20150595

Abstract

Abstract:

To search for potential energetic materials with large energy density and acceptable thermodynamics and kinetics stability, fifteen nitro uric acid derivatives were investigated by density functional theory. The detonation properties of all the molecules were evaluated according to Kamlet-Jacobs equations and specific impulses. Calculated results show that there are good linear relationships between detonation heat, densities, detonation velocities, detonation pressures and the numbers of nitro groups, respectively. It is found that tri-nitro and tetra-nitro uric acid derivatives show detonation velocity of about 8.0 km/s, and a detonation pressure of 30 GPa, and most of the investigated molecules have higher specific impulse than hexahydro-1,3,5-trinitro-s-triazine(RDX). By analyzing bond dissociation energies(BDEs) of N—NO₂ bonds, impact sensitivity, and the free space per molecule in the unit cell, most of the investigated molecules exhibit satisfactory stability(BDEs > 80 kJ/mol). The results of this study may provide basic information for the further study of this kind of compounds and the molecular design of novel energetic materials.

Key words: Energetic material, Density functional theory, Detonation performance, Polynitro-substituted uric acid derivative

CLC Number:

O641

TrendMD:

CHI Weijie, TIAN Meng, LI Quansong, LI Zesheng. Computational Studies on Energetic Performance of Polynitro-substituted Uric Acid Derivatives[J]. Chem. J. Chinese Universities, 2015, 36(11): 2189.

Figures/Tables 7

References 44

[1]	Zhang J., Zhang Q., Vo T. T., Parrish D. A., Shreeve J. M., J. Am. Chem. Soc., 2015, 137(4), 1697—1704
[2]	Bian C., Zhang M., Li C., Zhou Z., J. Mater. Chem. A, 2015, 3(1), 163—169
[3]	Rice B. M., Larentzos J. P., Byrd E. F., Weingarten N. S., J. Chem. Theory. Comput., 2015, 11(2), 392—405
[4]	Huynh M. H. V., Hiskey M. A., Chavez D. E., Naud D. L., Gilardi R. D., J. Am. Chem. Soc., 2005, 127(36), 12537—12543
[5]	Yin P., Parrish D. A., Shreeve J. M., J. Am. Chem. Soc., 2015, 137(14), 4778—4786
[6]	Chavez D. E., Hiskey M. A., J. Energ. Mater., 1999, 17(4), 357—377
[7]	Malow M., Wehrstedt K. D., Neuenfeld S., Tetrahedron. Lett., 2007, 48(7), 1233—1235
[8]	Lesnikovich A., Ivashkevich O., Levchik S., Balabanovich A., Gaponik P., Kulak A., Thermochim. Acta, 2002, 388(1), 233—251
[9]	Korkin A. A., Balkova A., Bartlett R. J., Boyd R. J., von Rague Schleyer P., J. Phys. Chem., 1996, 100(14), 5702—5714
[10]	Simões P., Pedroso L., Matos Beja A., Silva M. R., MacLean E., Portugal A., J. Phys. Chem. A, 2007, 111(1), 150—158
[11]	Li C., Liang L., Wang K., Bian C., Zhang J., Zhou Z., J. Mater. Chem. A, 2014, 2(42), 18097—18105
[12]	Sikder A., Sikder N., J. Hazard. Mater., 2004, 112(1), 1—15
[13]	Liu Y., Gong X., Wang L., Wang G., Xiao H., J. Phys. Chem. A, 2011, 115(9), 1754—1762
[14]	Pan Y., Zhu W., Xiao H., J. Mol. Model., 2012, 18(7), 3125—3138
[15]	Chi W., Li L., Li B., Wu H., Struct. Chem., 2012, 23(6), 1837—1841
[16]	Chi W., Li B., Wu H., Struct. Chem., 2013, 24(2), 375—381
[17]	Chi W. J., Li Z. S., RSC Adv., 2015, 5(10), 7766—7772
[18]	Chi W., Wang X., Li B., Wu H., J. Mol. Model., 2012, 18(9), 4217—4223
[19]	Guo Y. Y., Chi W. J., Li Z. S., Li Q. S., RSC Adv., 2015, 5(48), 38048—38055
[20]	Liu X. F., Xu W. G., Lu S. X., Chem. J. Chinese. Universities, 2009, 30(7), 1406—1409
[21]	Frisch M.J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A., Vreven T. Jr., Kudin K. N., Burant J. C., Millam J. M., Iyengar S., Tomasi S. J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Nanayakkara Y., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A., Gaussian 09, Revision D. 01, Gaussian Inc., Wallingford CT, 2009
[22]	Zhang X., Zhu W., Xiao H., J. Phys. Chem. A, 2009, 114(1), 603—612
[23]	Chen Z., Xiao J., Xiao H., Chiu Y., J. Phys. Chem. A, 1999, 103(40), 8062—8066
[24]
[25]	Politzer P., Murray J. S., Edward Grice M., Desalvo M., Miller E., Mol. Phys., 1997, 91(5), 923—928
[26]	Byrd E. F., Rice B. M., J. Phys. Chem. A, 2006, 110(3), 1005—1013
[27]	Rice B. M., Pai S. V., Hare J., Combust. Flame, 1999, 118(3), 445—458
[28]	Kamlet M., Jacobs S., J. Chem. Phys., 1968, 48, 23—35
[29]	Bulat F. A., Toro-Labbé A., Brinck T., Murray J. S., Politzer P., J. Mol. Model., 2010, 16(11), 1679—1691
[30]	Wei T., Zhu W., Zhang J., Xiao H., J. Hazard. Mater., 2010, 179(1), 581—590
[31]	He P., Zhang J. G., Wang K., Yin X., Zhang T. L., J. Org. Chem., 2015, 80(11), 5643—5651
[32]	Ghule V. D., Jadhav P. M., Patil R. S., Radhakrishnan S., Soman T., J. Phys. Chem. A, 2010, 114(1), 498—503
[33]	Ghule V. D., J. Phys. Chem. A, 2012, 116(37), 9391—9397
[34]	Chi W. J., Li L. L., Li B. T., Wu H. S., J. Mol. Model., 2012, 18(8), 3695—3704
[35]	Ma Q., Jiang T., Zhang X., Fan G., Wang J., Huang J., J. Phys. Org. Chem., 2015, 28(1), 31—39
[36]	Politzer P., Murray J. S., Cent. Eur. J. Energ. Mater., 2011, 8(3), 209—220
[37]	Hoffmann R., J. Chem. Soc., 1969, 5, 240—241
[38]	Liu H., Wang F., Wang G. X., Gong X. D., J. Comput. Chem., 2012, 33(22), 1790—1796
[39]	Fan X. W., Ju X. H., Xiao H. M., Qiu L., J. Mol. Struct: Theochem., 2006, 801(1), 55—62
[40]	Owens F., J. Mol. Struct: Theochem., 1996, 370(1), 11—16
[41]	Ravi P., Mol. Phys., 2015, 113(7), 647—655
[42]	Fried L. E., Manaa M. R., Pagoria P. F., Simpson R. L., Ann. Rev. Mater. Res., 2001, 31(1), 291—321
[43]	Politzer P., Murray J. S., J. Mol. Struct., 1996, 376(1), 419—424
[44]	Pospíšil M., Vávra P., Concha M. C., Murray J. S., Politzer P., J. Mol. Model., 2011, 17(10), 2569—2574

Compound	HOF_g/ (kJ·mol^-1)	ΔH_sub/ (kJ·mol^-1)	HOF_s/ (kJ·mol^-1)	ΔH_comb/ (kJ·g^-1)	Compound	HOF_g/ (kJ·mol^-1)	ΔH_sub/ (kJ·mol^-1)	HOF_s/ (kJ·mol^-1)	ΔH_comb/ (kJ·g^-1)
U1	-513.96	101.97	-615.92	-8.36	U24	-436.23	110.54	-546.77	-6.61
U2	-529.67	109.81	-639.48	-8.25	U34	-422.47	106.60	-529.07	-6.68
U3	-550.33	99.51	-649.84	-8.20	U123	-336.94	116.09	-453.03	-5.47
U4	-530.90	101.32	-632.22	-8.28	U124	-320.26	119.48	-439.74	-5.51
U12	-420.53	112.64	-533.17	-6.67	U134	-307.40	115.58	-422.98	-5.57
U13	-441.04	106.18	-547.21	-6.61	U234	-313.71	113.92	-427.63	-5.55
U14	-418.24	108.65	-526.90	-6.69	U1234	-196.07	124.71	-320.78	-4.73
U23	-449.42	108.26	-557.69	-6.57

Compound	HOF_g/ (kJ·mol^-1)	ΔH_sub/ (kJ·mol^-1)	HOF_s/ (kJ·mol^-1)	ΔH_comb/ (kJ·g^-1)	Compound	HOF_g/ (kJ·mol^-1)	ΔH_sub/ (kJ·mol^-1)	HOF_s/ (kJ·mol^-1)	ΔH_comb/ (kJ·g^-1)
U1	-513.96	101.97	-615.92	-8.36	U24	-436.23	110.54	-546.77	-6.61
U2	-529.67	109.81	-639.48	-8.25	U34	-422.47	106.60	-529.07	-6.68
U3	-550.33	99.51	-649.84	-8.20	U123	-336.94	116.09	-453.03	-5.47
U4	-530.90	101.32	-632.22	-8.28	U124	-320.26	119.48	-439.74	-5.51
U12	-420.53	112.64	-533.17	-6.67	U134	-307.40	115.58	-422.98	-5.57
U13	-441.04	106.18	-547.21	-6.61	U234	-313.71	113.92	-427.63	-5.55
U14	-418.24	108.65	-526.90	-6.69	U1234	-196.07	124.71	-320.78	-4.73
U23	-449.42	108.26	-557.69	-6.57

Compound	Q / (kJ·mol^-1)	ρ/(g·cm^-3)	D / (k·ms^-1)	P/GPa	Compound	Q / (kJ·mol^-1)	ρ/(g·cm^-3)	D / (k·ms^-1)	P/GPa
U1	488.64	1.83	6.19	18.66	U24	811.13	1.97	7.59	28.19
U2	462.21	1.93	6.33	20.28	U34	827.53	1.92	7.49	26.96
U3	450.59	1.87	6.17	18.76	U123	1057.23	1.97	8.28	33.11
U4	470.36	1.90	6.28	19.66	U124	1067.70	1.98	8.31	33.42
U12	823.73	1.95	7.57	27.86	U134	1080.93	1.99	8.38	34.08
U13	810.72	1.94	7.51	27.32	U234	1077.26	1.98	8.33	33.52
U14	829.54	1.89	7.43	26.35	U1234	1266.12	2.00	8.86	37.93
U23	801.02	1.94	7.50	27.26	RDX	1591.03	1.81	8.75	34.00

Compound	Q / (kJ·mol^-1)	ρ/(g·cm^-3)	D / (k·ms^-1)	P/GPa	Compound	Q / (kJ·mol^-1)	ρ/(g·cm^-3)	D / (k·ms^-1)	P/GPa
U1	488.64	1.83	6.19	18.66	U24	811.13	1.97	7.59	28.19
U2	462.21	1.93	6.33	20.28	U34	827.53	1.92	7.49	26.96
U3	450.59	1.87	6.17	18.76	U123	1057.23	1.97	8.28	33.11
U4	470.36	1.90	6.28	19.66	U124	1067.70	1.98	8.31	33.42
U12	823.73	1.95	7.57	27.86	U134	1080.93	1.99	8.38	34.08
U13	810.72	1.94	7.51	27.32	U234	1077.26	1.98	8.33	33.52
U14	829.54	1.89	7.43	26.35	U1234	1266.12	2.00	8.86	37.93
U23	801.02	1.94	7.50	27.26	RDX	1591.03	1.81	8.75	34.00

Compound	N	T_c	I_s	Compound	N	T_c	I_s
U1	0.0270	9766.7	16.24	U24	0.0271	7627.1	14.39
U2	0.0270	9641.4	16.13	U34	0.0271	7703.1	14.46
U3	0.0270	9586.3	16.09	U123	0.0272	6266.9	13.06
U4	0.0270	9680.0	16.17	U124	0.0272	6314.7	13.11
U12	0.0271	7685.5	14.44	U134	0.0272	6375.1	13.17
U13	0.0271	7625.2	14.38	U234	0.0272	6358.4	13.16
U14	0.0271	7712.5	14.47	U1234	0.0273	5720.7	12.50
U23	0.0271	7580.3	14.34	RDX			14.13