Abstract
The results of the computational studies performed on 1,2,4-triazolium cation-based salts designed by pairing it with energetic nitro-substituted 5- membered N-heterocyclic anions such as 5-nitrotetrazolate, 3,5-dinitrotriazolate, and 2,4,5 trinitroimidazolate are reported. Condensed phase heats of formation of the designed ionic salts and their thermodynamic and energetic properties have also been calculated. The results show that these salts are potential energetic materials and possess high positive heats of formation. The detonation velocity, D, and detonation pressure, P, have been calculated using the Kamlet-Jacobs equation and found to be 7–8 km/s and 25–29 GPa, respectively. These values fall in the range of the criteria to designate them as high-energy-density materials. Nucleus independent chemical shift (NICS) studies performed on the designed molecules show that these salts are stable in nature.
Similar content being viewed by others
References
Singh R P, Verma R D, Meshari D T and Shreeve J M 2006 Angew. Chem. Int. Ed. 45 3584
Tao G H, Gao Y, Parrish D A and Shreeve J M 2010 J. Mater. Chem. 20 2999
Xue H, Goa Y, Twamley B and Shreeve J M 2005 J. Mater. Chem. 15 3459
Xue H, Goa Y, Twamley B and Shreeve J M 2005 Chem. Mater. 17 191
Ghule V D, Sarangapani R P, Jadhav M and Tewari S P 2011 J. Mol. Model. 17 1507
Gao H and Shreeve J M 2011 Chem. Rev. 111 7377
Xue H, Gao H, Twamley B and Shreeve J M 2004 J. Org. Chem 69 1397
Xue H, Goa Y, Twamley B and Shreeve J M 2005 Inorg. Chem. 44 5068
Schmidt M W, Gordon M S and Boatz J A 2005 J. Phys. Chem. A. 109 7285
Gutowski K E, Rogers R D and Dixon A D 2007 J. Phys. Chem. B. 111 4788
Meot-Ner M, Liebermann J F and Del Bene J E 1986 J. Org. Chem 51 1105
Darwich C, Klapötke T M and Sabaté C M 2008 Chem. Eur. J. 14 5756
Mirzaei Y R, Xue H and Shreeve J M 2004 Inorg. Chem. 43 361
Xue H, Arritt S W and Twamley B 2004 Inor. Chem. 43 7972
Darwich C, Karagiosoff K, Klapotke T M and Sabate C M 2008 J. Allg. Chem. 634 61
Schleyer P R, Maerker C, Dransfeld A, Jiao H and Hommes N J R E 1996 J. Am. Chem. Soc. 118 6317
Chen Z, Wannere C S, Corminboeuf C, Puchta R and Schleyer P R 2005 Chem. Rev. 105 3842
Wolinski K, Hilton J F and Pulay P 1990 J. Am. Chem. Soc. 112 8251
Frisch M J, Trucks G W, Schlegel H B Scuseria G E, Robb M A, Cheeseman J R, Montgomery J A, Vreven T, Kudin K N, Burant J C, Millam J M, Iyengar S S, Tomasi 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, 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 Y, Nanayakkara A, Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C and Pople J A 2010 Gaussian 09 (Wallingford CT: Gaussian, Inc.)
Li M, Xu H and Wu F 2014 J Mol. Model. 20 2204
Chen P C, Chieh Y C and Tzeng S C 2003 Mol. Str.: THEO. 634 215
Singh H J, Gupta S and Sengupta S K 2014 RSC Adv 4 40534
Hehre W J, Ditchfield R, Radom L and Pople J A 1970 J. Amer. Chem. Soc. 92 4796
Xu X J, Xiao H M, Ju X H, Gong X D and Zhu W H 2006 J. Phys. Chem. A 110 5929
Zhang X W, Zhu W H and Xiao H M 2010 J. Phys. Chem. A 114 603
NIST Chemistry WebBook. Available at http://webbook.nist.gov/chemistry/ (Accessed October 3, 2014)
Jenkins H D B, Tudela D and Glasser L 2002 Inorg. Chem. 41 2364
Jenkins H D B and Liebman J F 2005 Inorg. Chem. 44 6359
Galvez-Ruiz J C, Holl G, Karaghiosoff K, Klapotke T M, Lohnwitz K, Mayer P, Noth H, Polborn K, Rohbogner C J, Suter M and Weigand J J 2005 Inorg. Chem. 44 4237
Gao H, Ye C, Winter R W, Gard G L, Sitzmann M E and Shreeve J M 2006 Eur. J. Inorg. Chem. 16 3221
Rice B M, Hare J J and Byrd E F C 2007 J Phys. Chem. A 111 10874
Hofmann D W M 2002 Acta Crystallogr. B 58 489
Klapotke T M, Stierstorfer J, Jenkins H D B, Eldik R V and Schmeisser M Z 2011 Anorg. Allg. Chem 637 1308
Kamlet M J and Jacobs S J 1968 J. Chem. Phys. 48 23
Lazzeri P 2004 Phys. Chem. Chem. Phys. 6 217
Aihara J 2002 Chem. Phys. Lett. 365 34
Keshavarz M H 2005 J. Haz. Mat. 121 31
Zhang X, Zhu W, Wei T, Zhang C and Xiao H 2010 J. Phys. Chem. 114 13142
Gao H, Ye C, Piekarski C M and Shreeve J M 2007 J. Phys. Chem. C 111 10718
Keshavarz M H and Pouretedal H R 2004 Therm. Acta. 414 203
Keshavarz M H 2007 Indian J. Eng. Mater. Sci. 14 324
Acknowledgements
One of the authors (RS) is thankful to UGC, New Delhi, for providing financial support under its DSA (BSR) programme. Thanks are also due to the Head of the Chemistry Department for allowing Authors to avail the necessary computational facilities of the department. The authors are thankful to a reviewer for very relevant and supportive suggestions to improve the quality of the manuscript.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
SINGH, R., SINGH, H.J. & SENGUPTA, S.K. Computational studies on 1,2,4-Triazolium-based salts as energetic materials. J Chem Sci 127, 1099–1107 (2015). https://doi.org/10.1007/s12039-015-0863-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-015-0863-5