A computational approach to design energetic ionic liquids

Journal of Molecular Modeling

Volumn 19, Issue 6, 2013, Pages 2317-2327

  Singh, Hari Ji ^a   Mukherjee, Uttama ^a  

^a D D U GORAKHPUR UNIVERSITY   (India)

Author keywords

Counterpoise (CP) correction; Ion pair binding energy; Ionic liquids; Nucleus independent chemical shift (NICS); Volume based thermodynamics (VBT)

Indexed keywords

1 BUTYL 2,4 DINITRO 3 METHYL IMIDAZOLIUM ION; 3,5 DINITRO 1,2,4 TRIAZOLATE ANION; ANION; CATION; DINITRAMIDE; EXPLOSIVE; IONIC LIQUID; NITRATE; PERCHLORATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL INTERACTION; ELECTRIC POTENTIAL; ENERGY TRANSFER; MATHEMATICAL COMPUTING; POLARIZATION; PRIORITY JOURNAL; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 84878749688     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-013-1775-2     Document Type: Article

References (62)

1. Plechkova NV, Seddon KR (2008) Applications of ionic liquids in chemical industries. Chem Soc Rev 37:123-150
2. Smiglak M, Metlen A, Rogers RD (2007) The second evolution of ionic liquids: from solvents and separations to advanced materials - energetic examples from the ionic liquid cookbook. Acc Chem Res 40:1182-1192
3. Hough WL, Smiglak M, Rodriguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE, Carliss RD, Soutullo MD, Davis JH, Rogers RD (2007) The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 31:1429-1436
4. 3 (X = F, Cl) systems. J Solut Chem 36:549-561
5. Vijay D, Zipse H, Sastry GN (2008) On the cooperativity of cation-π and hydrogen bonding interactions. Phys Chem B 112:8863-8867
6. Rappe' AK, Bernstein ER (2000) Ab initio calculations of non-bonded interactions: are we there yet? J Phys Chem A 104:6117-6128
7. Hadzi D (1997) Theoretical treatments of hydrogen bonding. Wiley, New York
8. Holbrey JD, Reichert WM, Nieuwenhuyzen M, Johnston S, Seddon KR, Rogers RD (2003) Crystal polymorphism in 1-butyl-3-methylimidazolium halides: supporting ionic liquid formation by inhibition of crystallization. Chem Commun 14:1636-1637
9. Holbrey JD, Reichert WM, Nieuwenhuyzen M, Sheppard O, Hardacre C, Rogers RD (2003) Liquid clathrate formation in ionic liquid - aromatic mixtures. Chem Commun 4:476-477
10. Berg RW, Deetlefs M, Seddon KR, Shim I, Thompson JM (2005) Raman and ab initio studies of simple and binary 1-alkyl-3-methylimidazolium ionic liquids. J Phys Chem B 109:19018-19025
11. 2-H with anions. Phys Chem Chem Phys 9:4780-4784
12. Talaty ER, Raja S, Storhaug VJ, Dolle A, Carper WR (2004) Raman and Infrared spectra and ab initio calculations of C2-4MIM imidazolium hexafluorophosphate ionic liquids. J Phys Chem B 108:13177-13184
13. Hunt PA, Gould IR, Kirchner B (2007) The structure of imidazolium-based ionic liquids: insights from ion-pair interactions. Aust J Chem 60:9-14
14. Hunt PA, Kirchner B, Welton T (2006) Characterising the electronic structure of ionic liquids: an examination of the 1-butyl-3-methylimidazolium chloride ion pair. Chem Eur J 12:6762-6775
15. Dong K, Song Y, Liu X, Cheng W, Yao X, Zhang S (2011) Understanding structures and hydrogen bonds of ionic liquids at the electronic level. J Phys Chem B 116:1007-1017
16. Nobuoka K, Kitaoka S, Iio M, Harran T, Ishikawa Y (2007) Solute-solvent interactions in imidazolium camphorsulfonate ionic liquids. Phys Chem Chem Phys 9:5891-5896
17. - (X = Cl or Br) interaction in imidazolium halide ionic liquids. J Chem Phys 124:044504
18. Zorn DD, Boatz JA, Gordon MS (2006) Electronic structure studies of tetrazolium based ionic liquids. J Phys Chem B 110:11110-11119
19. +. Resonance 5:101-104
20. Aubuchon CM, Rector KD, Holmes W, Fayer MD (1999) Nitro group asymmetric stretching mode lifetimes of molecules used in energetic materials. Chem Phys Lett 299:84-90
21. Su X, Cheng X, Meng C, Yuan X (2009) Quantum chemical study on nitroimidazole, polynitroimidazole and their methyl derivatives. J Hazard Mater 161:551-558
22. Bracuti AJ (1995) Crystal structure of 2,4-dinitroimidazole. J Chem Crystallogr 25:625-627
23. Chapman RD, Wilson WS, Fronabarger JW, Merwin LH, Ostrom GS (2002) Prospects of fused polycyclic nitroazines as thermally insensitive energetic materials. Thermochim Acta 384:229-243
24. Rogers RD, Voth GA (2007) Ionic liquids. Acc Chem Res 40:1077-1078
25. Fernandes AM, Rocha MAA, Freire MG, Marrucho IM, Coutinho JAP, Santos Luis MNBF (2011) Evaluation of cation-anion interaction strength in ionic liquids. J Phys Chem B 115:4033-4041
26. Li W, Wu X, Qi C, Rong H, Gong L (2010) Study on the relationship between the interaction energy and the melting point of amino acid cation based ionic liquids. J Mol Struct 942:19-25
27. Jansen HB, Ros P (1969) Non-empirical molecular orbital calculations on the protonation of carbon monoxide. Chem Phys Lett 3:140-143
28. Liu B, McLean AD (1973) Accurate calculation of the attractive interaction of two ground state helium atoms. J Chem Phys 59:4557-4558
29. Boys SF, Bernardi F (1970) The calculations of small molecular interaction by the difference of separate total energies. Some procedures with reduced error. Mol Phys 19:553-566
30. Schleyer PvR et al. (1998) Encyclopedia of computational chemistry. Wiley, New York
31. Jensen F (2004) Introduction to computational chemistry. Wiley, New York
32. Schleyer PR, Maerker C, Dransfeld A, Jiao H, Hommes NJRE (1996) Nucleus-independent chemical shifts: a simple and efficient aromaticity probe. J Am Chem Soc 118:6317-6318
33. Martin NH, Teague MR, Mills KH (2010) Computed NMR shielding effects over fused aromatic/antiaromatic hydrocarbons. Symmetry 2:418-436
34. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Barone V, Mennucci B, Petersson GA, Carikato M, Li X, Nakatsuji H, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T Jr, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian Inc., Wallingford
35. Salvador P, Fradera X, Duran M (2000) Effect of basis set superposition error on the electron density of molecular complexes. J Chem Phys 112:10106-10115
36. Wolinski K, Hilton JF, Pulay P (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc 112:8251-8260
37. Lazzeretti P (2004) Assessment of aromaticity via molecular response properties. Phys Chem Chem Phys 6:217-223
38. Aihara J (2002) Nucleus-independent chemical shifts and local aromaticities in large polycyclic aromatic hydrocarbons. Chem Phys Lett 365:34-39
39. Jenkins HDB, Liebman JF (2005) Volumes of solid state ions and their estimation. Inorg Chem 44:6359-6372
40. Galvez-Ruiz JC, Holl G, Karaghiosoff K, Klapotke TM, Lohnwitz K, Mayer P, Noth H, Polborn K, Rohbogner CJ, Suter M, Weigand JJ (2005) Derivatives of 1,5-diamino-1H-tetrazole: a new family of energetic heterocyclic based salts. J Inorg Chem 44:4237-4253
41. Schmidt MW, Gordon MS, Boatz JA (2005) Triazolium-based energetic ionic liquids. J Phys Chem A 109:7285-7295
42. 5) containing energetic salts. Eur J Inorg Chem 16:3221-3226
43. Xue H, Gao H, Twamley B, Shreeve JM (2006) Energetic nitrate, perchlorate, azide and azolate salts of hexamethylenetetramine. Eur J Inorg Chem 15:2959-2965
44. Gao Y, Ye C, Twamley B, Shreeve JM (2006) Energetic bicyclic azolium salts. Chem Eur J 12:9010-9018
45. Jenkins HDB, Roobottom HK, Passmore J, Glasser L (1999) Relationships among ionic lattice energies, molecular (formula unit) volumes, and thermochemical radii. Inorg Chem 38:3609-3620
46. 4], on the basis of CBS-4M and CHEETAH computations supplemented by VBT estimates. Anorg Allg Chem 637:1308-1313
47. Politzer P, Martinez J, Murray JS, Concha MC (2010) An electrostatic correction for improved crystal density prediction. Mol Phys 108:1391-1396
48. Rice BM, Hare JJ, Byrd EFC (2007) Accurate predictions of crystal densities using quantum chemical molecular volumes. J Phys Chem A 111:10874-10879
49. Wei T, Zhu WH, Zhang XW, Li YF, Xiao HM (2009) Molecular design of 1,2,4,5-tetrazine-based high-energy density materials. J Phys Chem A 113:9404-9412
50. Wei T, Zhu WH, Zhang JJ, Xiao HM (2010) DFT study on energetic tetrazolo-[1,5-b]-1,2,4,5-tetrazineand1,2,4-triazolo-[4,3-b]-1,2,4,5-tetrazine derivatives. J Hazard Mater 179:581-590
51. Zhang XW, Zhu WH, Xiao HM (2010) Theoretical studies on heats of formation, detonation properties, and bond dissociation energies of monofurazan derivatives. Int J Quantum Chem 110:1549-1558
52. Hofmann DWM (2002) Fast estimation of crystal densities. Acta Crystallogr B 58:489-493
53. Jenkins HDB, Tudela D, Glasser L (2002) Lattice potential energy estimation for complex ionic salts from density measurements. Inorg Chem 41:2364-2367
54. Gao H, Ye C, Piekarski CM, Shreeve JM (2007) Computational characterization of energetic salts. J Phys Chem C 111:10718-10731
55. Nicolaides A, Rauk A, Glukhovtsev MN, Radom L (1996) Heats of formation from G2, G2(MP2) and G2(MP2, SVP) total energies. J Phys Chem 100:17460-17464
56. Keshavarz MH (2007) New research on hazardous materials. Nova Science, New York
57. Ravi P, Gore GM, Tewari SP, Sikder AK (2012) A DFT study of aminonitroimidazoles. J Mol Model 18:597-605
58. Zhao G, Lu M (2012) Theoretical studies on the structures and detonation properties of nitramine explosives containing benzene ring. J Mol Model 18:2443-2451
59. Gao Y, Gao H, Piekarski C, Shreeve JM (2007) Azolium salts functionalized with cyanomethyl, vinyl or propargyl substituents and dicyanamide, dinitramide, perchlorate and nitrate anions. Eur J Inorg Chem 31:4965-4972
60. Keshavarz MH (2007) Predicting heats of detonation of explosives via specified detonation products and elemental composition. Indian J Eng Mater Sci 14:324-330
61. Keshavarz MH (2005) A simple approach for determining detonation velocity of high explosive at any loading density. J Hazard Mater 121:31-36
62. Keshavarz MH, Pouretedal HR (2004) An empirical method for predicting detonation pressure of CHNOFCl explosives. Thermochim Acta 414:203-208