Theoretical Investigations on the Structure, Density, Thermodynamic and Performance Properties of Bis(2,2-dinitropropyl) Formal

摘要
图/表
参考文献(46)
相关文章 (15)

全文: PDF (513 KB) HTML (1 KB)
输出: BibTeX | EndNote (RIS)

摘要 Density functional method was used to investigate the IR spectrum, heat of forma- tion and thermal stability of a new energetic material bis(2,2-dinitropropyl) formal (BDNPF). The detonation velocity and pressure were evaluated by using the Kamlet-Jacobs equations based on the theoretical density and heat of formation. The bond dissociation energies for the weakest bonds were analyzed to investigate the thermal stability of the title compound. The results show that the C(1)-N(1) bond is predicted to be the trigger bond during pyrolysis. The crystal structure obtained by molecular mechanics belongs to theP2₁ space group, with the lattice parameters to be Z = 2, α = 11.5254, b = 6.2168, c = 9.5000 Å and ρ= 1.66 g/cm³.

	服务

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	E-mail Alert
	RSS
	作者相关文章
	张瑞州
	李小红

关键词 ： density functional theory, bis(2,2-dinitropropyl) formal, detonation properties, bond dissociation energy, thermodynamic properties

Abstract：Density functional method was used to investigate the IR spectrum, heat of forma- tion and thermal stability of a new energetic material bis(2,2-dinitropropyl) formal (BDNPF). The detonation velocity and pressure were evaluated by using the Kamlet-Jacobs equations based on the theoretical density and heat of formation. The bond dissociation energies for the weakest bonds were analyzed to investigate the thermal stability of the title compound. The results show that the C(1)-N(1) bond is predicted to be the trigger bond during pyrolysis. The crystal structure obtained by molecular mechanics belongs to theP2₁ space group, with the lattice parameters to be Z = 2, α = 11.5254, b = 6.2168, c = 9.5000 Å and ρ = 1.66 g/cm³.

Key words： density functional theory bis(2,2-dinitropropyl) formal detonation properties bond dissociation energy thermodynamic properties

收稿日期: 2013-06-13 出版日期: 2013-10-10

基金资助: This project was supported by the National Natural Science Foundation of China (No. U1304111), and China Postdoctoral Science Foundation (No. 2013M531361) and Jiangsu Planned Projects for Postdoctoral Research Funds (No. 1201015B)

通讯作者: 李小红: lorna639@126.com E-mail: lorna639@126.com

作者简介: 李小红: lorna639@126.com

引用本文:

张瑞州;李小红 . Theoretical Investigations on the Structure, Density, Thermodynamic and Performance Properties of Bis(2,2-dinitropropyl) Formal[J]. 结构化学, 2014, 33(1): 71-78.
ZHANG Rui-Zhou;LI Xiao-Hong. Theoretical Investigations on the Structure, Density, Thermodynamic and Performance Properties of Bis(2,2-dinitropropyl) Formal. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33(1): 71-78.

链接本文:

http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2014/V33/I1/71

(1) Joo, Y. H.; Jeong, W. B.; Cho, S. K.; Goh, U. M.; Lim, Y. G.; Moon, S. S. New synthesis and nitration of 1,2-bis(5-aminotetrazol-1-yl)ethane. Bull. Korean Chem. Soc. 2012, 33, 373-375.

(2) Provatas, A. Energetic polymers and plasticizers for explosive formulations—A review of recent advances. DSTOTR-0966 2000.

(3) Daniel, M. Polyurethane binder systems for polymer bonded explosives. DSTO-GD-0492 2006.

(4) Agrawal, J. P.; Hodgson, R. D. Organic Chemistry of Explosives. John Wiley & Sons Ltd., West Sussex: England 2007.

(5) Li, X. H.; Zhang, R. Z.; Yang, X. D. Density functional studies of the heats of formation of several nitroester compounds. J. Mol. Struct. (Theochem). 2007, 815,151-156.

(6) Ji, Y. P.; Li, P. R.; Wang, W.; Lan, Y.; Ding, F. A review of recent advances of energetic plasticizers. Chin. J. Explos. Propellants2005, 4, 47-51.

(7) Taylor, R. H.; Ala, H. Propellant energy management for tactical application. U. S. Patent, 5334270,1996-12-05.

(8) Li, X. H.; Fu, Z. M.; Zhang, X. Z. Computational DT studies on a series of toluene derivatives as potential high energy density compounds. Struct. Chem. 2012, 23, 515-524.

(9) Menke, K.; Eisele, S. Rocket propellants with reduced smoke and high burning rates. Propellants Explos. Pyrotech. 1997, 22, 112-119.

(10) Marsh, N.; Marsh, A. A short history of nitroglycerine and nitric oxide in pharmacology and physiology. Clin. Exp. Pharmacol. Physiol. 2000, 27, 313-319.

(11) Akhavan, J. The Chemistry of Explosives. 2nd ed., The Royal Society of Chemistry: UK 2004.

(12) Camp, A. T.; Dickinson, L. A.; Mosher, P. R. Liquid Nitrate Ester Monopropellant Composition. U. S. Patent, 3634158, 1972-01-01.

(13) Preston, S. B. Co-nitration of Trimethylolethane and Triethylene Glycol.U. S. Patent, 5454891 1995-10-03.

(14) Barrio, M. A.; Hu, J.; Zhou, P. Z.; Cauchon, N. Simultaneous determination of formic acid and formaldehyde in pharmaceutical excipients using headspace GC/MS. J. Pharm. Biomed. Anal. 2006, 41, 738-743.

(15) Jang, M.; Kamens, R. M. Atmospheric secondary aerosol formation by heterogeneous reactions of aldehydes in the presence of a sulfuric acid aerosol catalyst. Environ. Sci. Technol.2001, 35, 4758-4766.

(16) Kim, J. S.; Cho, J. R.; Lee, K. D.; Kim, J. K. Glycidyl dinitropropyl formal, poly(glycidyl dinitropropyl formal) and preparation method thereof. U. S. Patent, 00566632007-03-04.

(17) Lenskii, M. A.; Shul’ts, E. E.; Androshchuk, A. A.; Tolstikov, G. A. Reaction of triphenyl borate with 1,3,5-trioxane. Russ. J. Org. Chem. 2009, 45, 1772-1775.

(18) Barsanti, K. C.; Pankow, J. F. Thermodynamics of the formation of atmospheric organic particulate matter by accretion reactions—Part 1. Aldehydes and ketones. Atmos. Environ.2004, 38, 4371-4382.

(19) Jang, M.; Czoschke, N. M.; Lee, S.; Kamens, R. M. Heterogeneous atmospheric aerosol production by acid-catalyzed particle phase reactions. Science 2002, 298, 814-817.

(20) Chen, Y.; Kwon, Y.; Kim, J. S. Synthesis and characterization of bis(2,2-dinitropropyl ethylene) formal plasticizer for energetic binders. J. Ind. Eng. Chem.2012, 18, 1069-1075.

(21) Turker, L.; Atalar, T.; Gumus, S.; Camur, Y. A DFT study on nitrotriazines. J. Hazard. Mater. 2009, 167, 440-448.

(22) Li, X. H.; Zhang, R. Z.; Zhang, X. Z. Theoretical studies of 1,2,4,5-tetrazine-based energetic nitro-rich compounds. Struct. Chem. 2013, 24, 393–400.

(23) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. J.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, K.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, Revision B. 01. Gaussian, Inc.: Pittsburgh PA 2003.

(24) Becke, A. D. Density-functional thermochemistry. II. The effect of the Perdew-Wang generalized-gradient correlation correction. J. Chem. Phys. 1992, 97, 9173-9177.

(25) Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785-789.

(26) Hill, T. L. Introduction to statistic thermodynamics. Addison-Wesley: New York 1960.

(27) Carpenter, J. E.; Weinhold, F. Analysis of the geometry of the hydroxymethyl radical by the "different hybrids for different spins" natural bond orbital procedure. J. Mol. Struct. (Theochem). 1988-62. , 169, 41

(28) Kamlet, M. J.; Jacobs, S. J. Chemistry of detonation: simple method of calculation detonation properties of CHNO explosives. J. Chem. Phys. 1968, 48, 23-35.

(29) Zhang, X. H.; Yun, Z. H. Explosive Chemistry. National Defense Industry Press: Beijing 1989.

(30) Atkins, P. W. Physical Chemistry. Oxford University Press: Oxford 1982.

(31) Politzer, P.; Lane, P.; Murray, J. S. Computational characterization of a potential energetic compound: 1,3,5,7-tetranitro-2,4,6,8-tetraazacubane. Cent. Eur. J. Energ. Mater. 2011, 8, 39-52.

(32) Politzer, P.; Murray, J. S. Some perspectives on estimating detonation properties of C, H, N, O compounds. Cent. Eur. J. Energ. Mat. 2011, 8, 209–220.

(33) Byrd, E. F. C.; Rice, B. M. Improved prediction of heats of formation of energetic materials using quantum mechanical calculations. J. Phys. Chem. A 2006, 110, 1005–1013.

(34) Lu, T. Multiwfn Revision 2. 5. 2, Beijing Science and Technology: Beijing 2012.

(35) Materials Studio Blends Module, Version 4. 4; software for miscibility estimation: Theory in Blends; Accelrys Software Inc.: San Diego, CA 2008.

(36) Mighell, A. D.; Himes, V. L.; Rodgers, J. R. Space group frequencies for organic compounds. Acta Crystallogr. 1983, 39, 737-740.

(37) Srinivasan, R. On space-group frequencies. Acta Crystallogr. A 1992, 48, 917-918.

(38) Sasada, Y. Molecular and Crystal Structures in Chemistry Handbook. 3rd edn. The Chemical Society of Japan Maruzen: Tokyo 1984.

(39) Hehre, W. J.; Radom, L.; Schleyer, P. V. R. Ab Initio Molecular Orbital Theory. Wiley: New York 1986.

(40) Lide, D. R. Handbook of Chemistry and Physics. 84th edn. CRC Press LLC: Boca Raton 2004.

(41) Pilcher, G.;-505. Pell, A. S.; Coleman, D. J. Measurements of heats of combustion by flame calorimetry. Part 2-Dimethyl ether, methyl ethyl ether, methyl n-propyl ether, methyl isopropyl ether. Trans. Faraday Soc. 1964, 60, 499

(42) Xiao, H. M. Structures and Properties of Energetic Compounds. National Defense Industrial Press: Beijing 2004.

(43) Shao, J. X.; Cheng, X. L.; Yang, X. D.; Xiang, S. K. Computation of bond dissociation energies for removal of nitrogen dioxide groups in certain aliphatic nitro compounds. Chin. Phys. Lett. 2006, 23, 819-821.

(44) Li, X. H.; Zhang, R. Z.; Zhang, X. Z. Computational study of imidazole derivative as high energetic materials. J. Hazard. Mater. 2010, 183, 622-631.

(45) Clark, S. J.; Segall, M. D.; Pickard, C. J.; Hasnip, P. J.; Probert, M. J.; Refson, K.; Payne, M. C. Z. First principles methods using CASTEP Kristallogr. 2005, 220, 567−570.

(46) Xu, X. J.; Zhu, W. H.; Xiao, H. M. DFT studies on the four polymorphs of crystalline CL-20 and the influences of hydrostatic pressure on ε-CL-20 crystal. J. Phys. Chem. B 2007, 111, 2090-2097.