Skip to main content
Log in

Theoretical investigation on the structure and thermodynamic properties of the 2,4-dinitroimidazole complex with methanol

  • Original Paper
  • Published:
Journal of Molecular Modeling Aims and scope Submit manuscript

Abstract

The structure and thermodynamic properties of the 2, 4-dinitroimidazole complex with methanol were investigated using the B3LYP and MP2(full) methods with the 6-31++G(2d,p) and 6-311++G(3df,2p) basis sets. Four types of hydrogen bonds [N–H⋯O, C–H⋯O, O–H⋯O (nitro oxygen) and O–H⋯π] were found. The hydrogen-bonded complex having the highest binding energy had a N–H⋯O hydrogen bond. Analyses of natural bond orbital (NBO) and atoms-in-molecules (AIM) revealed the nature of the intermolecular hydrogen-binding interaction. The changes in thermodynamic properties from monomers to complexes with temperatures ranging from 200.0 to 800.0 K were investigated using the statistical thermodynamic method. Hydrogen-bonded complexes of 2,4-dinitroimidazole with methanol are fostered by low temperatures.

Molecular structures and bond critical points of 2,4-dinitroimidazole complexes at MP2(full)/6-311++G(3df,2p) level. Structure and thermodynamic property of the 2,4-dinitroimidazole complex with methanol are investigated using the B3LYP and MP2(full) methods with the 6-31++G(2d,p) and 6-311++G(3df,2p) basis sets. Four types of hydrogen bonds (N–H…O, C–H…O, O–H…O (nitro oxygen) and O–H…π) are found. For the hydrogen-bonded complex having the highest binding energy, there is a N–H…O hydrogen bond. The complex formed by the N–H…O hydrogen bond can be produced spontaneously at room temperature and the equilibrium constant is predicted to be 6.354 and 1.219 at 1 atm with the temperature of 268.0 and 298.15 K, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Desiraju GR, Steiner T (1999) The weak hydrogen bond in structural chemistry and biology. Oxford University Press, New York

    Google Scholar 

  2. Cao D, Ren F, Feng X, Wang J, Li Y, Hu Z, Chen S (2008) J Mol Struct THEOCHEM 849:76–83

    Article  CAS  Google Scholar 

  3. Bulusu S, Damavarapu R, Autera JR, Behrens R Jr, Minier LM, Villanueva J, Jayasuriya K, Axenrod T (1995) J Phys Chem 99:5009–5015

    Article  CAS  Google Scholar 

  4. Liu HJ, Yang L, Cao DL (2005) J Energetic Mat 13:141–143

    CAS  Google Scholar 

  5. Fang GY, Xu LN, Xiao HM, Ju XH (2005) Acta Chim Sinica 63:1055–1061

    CAS  Google Scholar 

  6. Hrelia P, Fimognary C, Maffei F, Brighenti B, Garuti L, Burnelli S, Cantelli-Forti G (1998) Mutat Res 397:293–301

    Article  CAS  Google Scholar 

  7. Suwinski J, Salwinska E (1987) Pol J Chem 61:613–920

    Google Scholar 

  8. Grimmett MR, Hua ST, Chang KC, Foley SA, Simpson J (1989) Aust J Chem 42:1281–1289

    Article  CAS  Google Scholar 

  9. Li ZJ, Chu TW, Liu XQ, Wang XY (2005) Nucl Med Biol 32:225–231

    Article  CAS  Google Scholar 

  10. Anderson C, Beauchamp A (1995) Inorg Chim Acta 233:33–41

    Article  CAS  Google Scholar 

  11. Cho SG, Cheun YG, Park BS (1998) J Mol Struct THEOCHEM 432:41–53

    Article  CAS  Google Scholar 

  12. Cho SG, Park BS (1999) Int J Quantum Chem 72:145–154

    Article  CAS  Google Scholar 

  13. Gamézo VN, Odiot S, Blain M, Fliszár S, Delpuech A (1995) J Mol Struct THEOCHEM 337:189–197

    Article  Google Scholar 

  14. Flammang R, Elguero J, Le HT, Gerbaux P, Nguyen MT (2002) Chem Phys Lett 356:259–266

    Article  CAS  Google Scholar 

  15. Ramalho TC, de Alencastro RB, La-Scalea MA, Figueroa-Villar JD (2004) Biophys Chem 110:267–279

    Article  CAS  Google Scholar 

  16. Cho SG, Cho JR, Park BS, Park GJ (2000) Mol Struct THEOCHEM 532:279–286

    Article  CAS  Google Scholar 

  17. Breccia A, Cavalleri B, Adams GE (eds) (1982) Nitroimidazoles. Chemistry, pharmacology, and clinical application. Plenum, New York

    Google Scholar 

  18. Richard RM, Ball DW (2007) J Mol Struct THEOCHEM 806:113–120

    Article  CAS  Google Scholar 

  19. Macias AT, Norton JE, Evanseck JD (2003) J Am Chem Soc 125:2351–2360

    Article  CAS  Google Scholar 

  20. Suwattanamala A, Magalhaes AL, Gomes JANF (2005) Chem Phys 310:109–122

    Article  CAS  Google Scholar 

  21. Ruan C, Yang Z, Hallowita N, Rodgers MT (2005) J Phys Chem A 109:11539–11550

    Article  CAS  Google Scholar 

  22. Tanaka N, Tamezane T, Nishikiori H, Fujii T (2003) J Mol Struct THEOCHEM 631:21–28

    Article  CAS  Google Scholar 

  23. Koné M, Illien B, Graton J, Laurence C (2005) J Phys Chem A 109:11907–11913

    Article  Google Scholar 

  24. Koné M, Illien B, Laurence C, Graton J (2011) J Phys Chem A 115:13975–13985

    Article  Google Scholar 

  25. Laurence C, Gal JF (eds) (2009) Lewis basicity and affinity scales: Data and measurement. Wiley, Chichester

    Google Scholar 

  26. Frisch MJ, Trucks GA, Schlegel HB, Scuseria GE, Robb MA, Cheseman JR, Montgomery Jr JA, Vreeven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochtersky JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi L, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision B.03. Gaussian, Pittsburgh, PA

  27. Hill TL (1960) Introduction to statistic thermodynamics. Addison-Wesley, New York

    Google Scholar 

  28. Halls MD, Velkovski J, Schlegel HB (2001) Theor Chem Acc 105:413–421

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. Bader RFW (1999) Atoms in molecules, a quantum theory. Oxford University Press, Oxford

    Google Scholar 

  31. Biegler-König FW, Bader RFW, Tang TH (1982) J Comput Chem 3:317–328

    Article  Google Scholar 

  32. van Duijineveldt FB, van Duijineveldt-van de Rijdt JCM, van Lenthe JH (1994) Chem Rev 94:1873–1885

    Article  Google Scholar 

  33. Boys SF, Bernardi F (1970) Mol Phys 19:553–566

    Article  CAS  Google Scholar 

  34. Bondi A (1964) J Phys Chem 68:441–451

    Article  CAS  Google Scholar 

  35. Aakeröy CB, Evans TA, Seddon KR, Pálinkó I (1999) New J Chem 23:145–152

    Article  Google Scholar 

  36. Jiang JC, Tsai MH (1997) J Phys Chem A 101:1982–1988

    Article  CAS  Google Scholar 

  37. Rozas I, Alkorta I, Elguero J (1997) J Phys Chem A 101:9457–9463

    Article  CAS  Google Scholar 

  38. Shi FQ, An JY, Li W, Zhao S, Yu JY (2004) Acta Chim Sinica 62:1171–1175

    CAS  Google Scholar 

  39. Xu LN, Xiao HM, Fang GY, Ju XH (2005) Acta Chim Sinica 63:1062–1068

    CAS  Google Scholar 

  40. Chao J (1986) Int J Thermophys 7:431–442

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Wen-jing Shi.

Electronic supplementary material

The structures of all complexes are in Appendix A.

ESM 1

(DOC 49 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhao, Ss., Shi, Wj. & Wang, Jl. Theoretical investigation on the structure and thermodynamic properties of the 2,4-dinitroimidazole complex with methanol. J Mol Model 19, 163–171 (2013). https://doi.org/10.1007/s00894-012-1524-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00894-012-1524-y

Keywords

Navigation