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Quantum chemical studies on nanostructures of the hydrated methylimidazolium–based ionic liquids

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Abstract

The B3LYP and M06–2X suits of density functional theory in conjunction with the 6-311++G(2d,2p) basis set were employed to investigate the nanostructures formed from the interaction between water molecules and ionic liquids based on methylimidazolium cation (MIM+) with the anions (X1–5 = CH3COO, CF3COO, NO3 , BF4 , and N(CN)2 ) on a molecular level. Based on the calculated Gibbs free binding energies, the predicted stability order of nanostructures in the gas phase is [MIM]X1 > [MIM]X2 > [MIM]X3 > [MIM]X4 > [MIM]X5. The estimated solvation enthalpy of ions implied that the stability of anions NO3 and CH3COO in water is greater than those of MIM+ and other anions. Tendency of hydrated anions to react with hydrated cations to form the solvated ion pairs is slightly smaller than the tendency of hydrated anions (cations) to react with unsolvated cations (anions). The strengths of the interactions in studied categories follow the trend X–W > MIM–W > [MIM]X –W.

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References

  1. Wasserscheid P, Welton T (eds) (2003) Ionic liquids in synthesis. Wiley-VCH, Weinheim

    Google Scholar 

  2. Fedorov MV, Kornyshev AA (2014) Chem Rev 114:2978–3036

    Article  CAS  Google Scholar 

  3. Hapiot P, Lagrost C (2008) Chem Rev 108:2238–2264

    Article  CAS  Google Scholar 

  4. Welton T (1999) Chem Rev 99:2071–2084

    Article  CAS  Google Scholar 

  5. Dupont J, De Souza RF, Suarez PA (2002) Chem Rev 102:3667–3692

    Article  CAS  Google Scholar 

  6. Weingartner H (2008) Angew Chem Int Ed 47:654–670

    Article  Google Scholar 

  7. Hu XB, Sun Y, Mao JY, Li HR (2010) J Catal 272:320–332

    Article  CAS  Google Scholar 

  8. Yu GR, Chen XC, Asumana C, Zhang SJ, Liu XM, Zhou GH (2011) AIChE J 57:507–516

    Article  CAS  Google Scholar 

  9. Gardas RL, Coutinho JAP (2009) AIChE J 55:1274–1290

    Article  CAS  Google Scholar 

  10. Singh T, Kumar T (2007) J Phys Chem B 111:7843–7851

    Article  CAS  Google Scholar 

  11. Martins MAP, Frizzo CP, Moreira DN, Zanatta N, Bonacorso HG (2008) Chem Rev 108:2015–2050

    Article  CAS  Google Scholar 

  12. Triolo A, Russina O, Bleif H, Cola E J Phys Chem B 111:4641–4644

  13. Pârvulescu VI, Hardacre C (2007) Chem Rev 107:2615–2665

    Article  Google Scholar 

  14. Dupont J, de Souza RF (2002) Chem Rev 102:3667–3691

    Article  CAS  Google Scholar 

  15. Song CE (2004) Chem Commun 1033–1043

  16. Baudequin C, Baudoux J, Levillain J, Cahard D, Gaumont AC, Plaquevent JC (2003) Tetrahedron Asymmetry 14:3081–3093

    Article  CAS  Google Scholar 

  17. Visser AE, Swatloski RP, Reichert WM, Griffin ST, Rogers RD (2000) Ind Eng Chem Res 39:3596–3604

    Article  CAS  Google Scholar 

  18. Cammarata L, Kazarian SG, Salter PA, Welton T (2001) Phys Chem Chem Phys 3:5192–5200

    Article  CAS  Google Scholar 

  19. Koddermann T, Wertz C, Heintz A, Ludwig R (2006) Angew Chem Int Ed 45:3697–3702

    Article  Google Scholar 

  20. Greaves TL, Drummond CJ (2013) Chem Soc Rev 42:1096—1120 and references cited therein

  21. Russina O, Triolo A, Gontrani L, Caminiti R (2012) J Phys Chem Lett 3:27–33

    Article  CAS  Google Scholar 

  22. Castner W, Margulis CJ, Maroncelli M, Wishart JF (2011) Annu Rev Phys Chem 62:85–105

    Article  CAS  Google Scholar 

  23. Dupont J (2011) Acc Chem Res 44:1223–1231

    Article  CAS  Google Scholar 

  24. Wang Y, Li H, Han S (2006) J Phys Chem B 110:24646–24651

    Article  CAS  Google Scholar 

  25. Cammarata L, Kazarian SG, Salter PA, Welton T (2001) Phys Chem Chem Phys 3:156–164

    Article  Google Scholar 

  26. Rivera-Rubero S, Baldelli SJ (2004) Am Chem Soc 126:11788–11789

    Article  CAS  Google Scholar 

  27. Baldelli SJ (2003) Phys Chem B 107:6148

    Article  Google Scholar 

  28. Downard A, Earle MJ, Hardacre C, McMath SE, Nieuwenhuyzen M, Teat SJ (2004) Chem Mater 16:43–48

    Article  CAS  Google Scholar 

  29. Tran CD, de Paoli Lacerda SH, Oliveira D (2003) Appl Spectrosc 57:152–156

    Article  CAS  Google Scholar 

  30. Ding ZD, Chi Zh GWX, Gu SM, Wang HJ (2012) J Mol Struct 1015:147–155

    Article  CAS  Google Scholar 

  31. Danten Y, Cabaço MI, Besnard M (2010) J Mol Liq 153:57–66

    Article  CAS  Google Scholar 

  32. Li W, Qi Ch WX, Rong H, Gong L (2008) J Mol Struct THEOCHEM 855:34–39

    Article  CAS  Google Scholar 

  33. Zhang Z, Salih AAM, Li M, Yang B (2014) Energy Fuels 28:2802–2810

    Article  CAS  Google Scholar 

  34. Pimienta ISO, Elzey S, Boatz JA, Gordon MS (2007) J Phys Chem A 111:691–703

    Article  CAS  Google Scholar 

  35. Fernandes AM, Rocha MAA, Freire MG, Marrucho IM, Coutinho JAP, Santos LMNBF (2011) J Phys Chem B 115:4033–4041 and references cited therein

  36. Roohi H, Moghadam B (2012) J Mol Model 18:1313–1324

    Article  CAS  Google Scholar 

  37. Annaraj B, Pan S, Neelakantan MA, Chattaraj PK (2014) Comput Theor Chem 1028:19–26

    Article  CAS  Google Scholar 

  38. Esseffar M, Jalal R, Aurell MJ, Domingo LR (2014) Comput Theor Chem 1030:25–32

    Article  CAS  Google Scholar 

  39. Morkan IA, Morkan AU (2011) Spectrochim Acta A 79:1715–1721

    Article  CAS  Google Scholar 

  40. Mancini PME, Ormachea CM, Della Rosa CD, Kneeteman MN, Suarez AG, Domingo LR (2012) Tetrahedron Lett 53:6508–6511

    Article  CAS  Google Scholar 

  41. Li W, Wu X, Qi C, Rong H, Gong L (2010) J Mol Struct THEOCHEM 942:19–25

    Article  CAS  Google Scholar 

  42. Pakiari AH, Siahrostami S, Ziegler T (2010) J Mol Struct THEOCHEM 955:47–52

    Article  CAS  Google Scholar 

  43. Shukla M, Saha S (2013) Comput Theor Chem 1015:27–33

    Article  CAS  Google Scholar 

  44. Vafaeezadeh M, Mahmoodi Hashemi M (2014) Chem Eng J 250:35–41

    Article  CAS  Google Scholar 

  45. Zhang Y, Chen XY, Wang HJ, Diao KS, Chen JM (2010) J Mol Struct THEOCHEM 952:16–24

    Article  CAS  Google Scholar 

  46. Becke AD (1993) J Chem Phys 98:5648–5652

    Article  CAS  Google Scholar 

  47. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  48. Zhao Y, Truhlar DG (2006) Theor Chem Accounts 120:215–241

    Article  Google Scholar 

  49. Feller D (1996) J Comput Chem 17(13):1571–1586

    Article  CAS  Google Scholar 

  50. Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999–3093 and references cited therein

  51. Pascual-Ahuir JL, Silla E, Tuñón I (1994) J Comput Chem 15:1127–1138

    Article  CAS  Google Scholar 

  52. Levine IN (2000) Quantum chemistry, 5th edn. Prentice Hall, New Jersey, p 596

    Google Scholar 

  53. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su S, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14:1347–1363

    Article  CAS  Google Scholar 

  54. Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899–926

    Article  CAS  Google Scholar 

  55. Glendening DE, Reed AE, Carpenter JE, Weinhold F NBO Version 3.1

  56. Roohi H, Khyrkhah S (2013) J Mol Liq 177:119–128

    Article  CAS  Google Scholar 

Download references

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Correspondence to Hossein Roohi.

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Roohi, H., Khyrkhah, S. Quantum chemical studies on nanostructures of the hydrated methylimidazolium–based ionic liquids. J Mol Model 21, 1 (2015). https://doi.org/10.1007/s00894-014-2561-5

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  • DOI: https://doi.org/10.1007/s00894-014-2561-5

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