Chinese Journal of Organic Chemistry >
Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers
Received date: 2018-08-20
Revised date: 2018-10-22
Online published: 2018-11-30
Supported by
Project supported by the National Natural Science Foundation of China (No. 51603103).
3,3-Bis(difluoroamino)-1,5-dinitratopentane was used as energetic plasticizer with improving energy properties and low glass transition temperature. To obtain more new difluoroamino energetic compounds with similar sturctures, a series of 3,3-bis(difluoroamino)-1,5-substituted-pentane derivatives were designed as candidates of novel energetic plasticizers. The heats of formation (HOFs), electronic structure, energy property and thermal stability were studied using density functional theory (DFT) method. The difluoroamino groups can increase energy gaps of electronic structure, density and detonation properties among the title compounds. Especially, 1,3,3,5-tetra(difluoroamino)pentane (S3) has given outstanding values of potential energetic plasticizer. Its crystal density (1.91 g/cm3), detonation velocity (9.01 km/s), detonation pressure (37.31 GPa) and impact sensitivity (h50 29.83 cm) are very close to those of cyclotetramethylenetetranitramine (HMX). Furthermore, S3 can be synthesized via some mature processes in five steps.
Wang Wanjun , Li Huan , Pan Renming , Zhu Weihua . Molecular Design and Property Prediction for a Series of 3,3-Bis(difluoroamino)-1,5-substituted-pentane Derivatized as Energetic Plasticizers[J]. Chinese Journal of Organic Chemistry, 2019 , 39(1) : 170 -176 . DOI: 10.6023/cjoc201808024
[1] Chapman, R. D. In Organic Difluoramine Derivatives, Vol. 125, Ed.:Klapötke, T. M., Springer, Berlin, 2007.
[2] Chapman, R. D.; Welker, M. F.; Kreutzberger, C. B. J. Org. Chem. 1998, 63, 1566.
[3] Chapman, R. D.; Gilardi, R. D.; Welker, M. F.; Kreutzberger, C. B. J. Org. Chem. 1999, 64, 960.
[4] Chapman, R. D.; Groshens, T. J. US 7632943, 2009[Chem. Abstr. 2009, 152, 57346].
[5] Zhang, J.; Oxley, J.; Smith, J.; Bedford, C.; Chapman, R. J. Mass Spectrom. 2000, 35, 841.
[6] Chapman, R. D.; Nguyen, B. V. US 6310204, 2001[Chem. Abstr. 2001, 135, 346536].
[7] Axenrod, T.; Guan, X. P.; Sun, J.; Qi, L.; Chapman, R. D.; Gliardi, R. D. Tetrahedron Lett. 2001, 42, 2621.
[8] Archibald, T. G.; Manser, G. E.; Immoos, J. E. US 5272249, 1993[Chem. Abstr. 1994, 120, 135476].
[9] Archibald, T. G.; Manser, G. E.; Immoos, J. E. US 5420311, 1995[Chem. Abstr. 1994, 120, 135476].
[10] Archibald, T. G.; Manser, G. E. US 5789617, 1998[Chem. Abstr. 1994, 120, 298071].
[11] Adolph, H. G.; Trivedi, N. J. US 6325876, 2001[Chem. Abstr. 2001, 136, 8637].
[12] Li, H.; Pan, R. M.; Wang, W. J.; Zhang, L. Y. Propellants, Explos., Pyrotech. 2014, 39, 819.
[13] Li, H.; Pan, R. M.; Wang, W. J.; Zhang, L. Y. J. Therm. Anal. Calorim. 2014, 118, 189.
[14] Li, H.; Pan, J. A.; Wang, W. J.; Pan, R. M.; Zhu, W. H. J. Macromol. Sci., Part A:Pure Appl. Chem. 2018, 55, 135.
[15] Wu, Q.; Zhu, W. H.; Xiao, H. M. J. Mol. Model. 2013, 19, 2945.
[16] Pan, Y.; Li, J. S.; Cheng, B. B.; Zhu, W. H.; Xiao, H. M. Comput. Theor. Chem. 2012, 992, 110.
[17] Wu, Q.; Pan, Y.; Zhu, W. H.; Xiao, H. M. J. Mol. Model. 2013, 19, 1853.
[18] Jensen, T. L.; Moxnes, J. F.; Kjønstad, E. F.; Unneberg, E. Cent. Eur. J. Energ. Mater. 2016, 13, 445.
[19] Xiang, D.; Chen, H.; Zhu, W. H.; Xiao, H. M. Can. J. Chem. 2016, 94, 667.
[20] Muthurajan, H.; Sivabalan, R.; Talawar, M. B.; Anniyappan, M.; Venugopalan, S. J. Hazard. Mater. 2006, 133, 30.
[21] Chen, Z. X.; Xiao J. M.; Xiao, H. M.; Chiu, Y. N. J. Phys. Chem. A 1999, 103, 8062.
[22] Ju, X. H.; Li, Y. M.; Xiao, H. M. J. Phys. Chem. A 2005, 109, 934.
[23] Ju, X. H.; Wang, X.; Bei, F. L. J. Comput. Chem. 2005, 26, 1263.
[24] Atkins, P. W. Physical Chemistry, Oxford University Press, Oxford, 1982.
[25] Politzer, P.; Murry, J. S.; Grice, M. E.; Salvo, M. De; Miller, E. Mol. Phys. 1997, 91, 923.
[26] Politzer, P.; Murry, J. S. Cent. Eur. J. Energ. Mater. 2011, 8, 209.
[27] Byrd, E. F. C.; Rice, B. M. J. Phys. Chem. A 2006, 110, 1005.
[28] Kamlet, M. J.; Jacobs, S. T. J. Chem. Phys. 1968, 48, 23.
[29] Sun, Y. B.; Hui, J. M.; Cao, X. M. Military Use of Blended Explosive, Weapon Industry Press, Beijing, 1995 (in Chinese). (孙业斌, 惠君明, 曹欣茂, 军用混合炸药, 兵器工业出版社, 北京, 1995.)
[30] Politzer, P.; Martines, J.; Murry, J. S.; Concha, M. C.; Toro-Labbé, A. Mol. Phys. 2009, 107, 2095.
[31] Pospíšil, M.; Vávra, P.; Concha, M. C.; Murry, J. S.; Politzer, P. J. Mol. Model. 2010, 16, 895.
[32] Benson, S. W. Thermochemical Kinetic, 2nd ed., Weily Interscience, New York, 1976.
[33] Mills, I.; Cvitas, T.; Homann, K.; Kallay, N.; Kuchitsu, K. Quantities, Units, and Symbols in Physical Chemistry, Blackwell Scientific Publications, Oxford, 1988.
[34] Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
[35] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; 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.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010.
[36] Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B:Condens. Matter Mater. Phys. 1988, 37, 785.
[37] Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
[38] Lu, T., and Chen, F. J. Comput. Chem. 2012, 33, 580.
[39] Dean, J. A. LANGE's Handbook of Chemistry, 13th ed., Mc Graw-Hill Book Co., New York, 1985.
[40] Dean, J. A. LANGE's Handbook of Chemistry, 15th ed., Mc Graw-Hill Book Co., New York, 1999.
[41] Joo, Y. H.; Shreeve, J. M. Angew. Chem., Int. Ed. 2009, 48, 564.
[42] Ghule, V. D.; Sarangapani, R.; Jadhav, P. M.; Pandey, R. K. J. Mol. Model. 2011, 17, 2927.
[43] Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
[44] Shen, C.; Wang, P. C.; Lu, M. J. Phys. Chem. A 2015, 119, 8250.
[45] Chung, G.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. A 2000, 104, 5647.
[46] Owen, G. R.; Reese, C. B. J. Chem. Soc. C 1970, 17, 2401.
[47] Kenji, H.; Tadashi, M.; Shaoji, S. JP 2007-070270, 2007[Chem. Abstr. 2007, 146, 358683].
[48] Haiges, R.; Wager, R.; Boatz, J. A.; Yousufuddin, M.; Etzkorn, M.; Prakash, G. K.; Christe, K. O.; Chapman, R. D.; Welker, M. F.; Kreutzberger. C. B. Angew. Chem., Int. Ed. 2006, 45, 5179.
/
| 〈 |
|
〉 |
