Skip to main content
SpringerLink
Log in

Solute–Solvent and Solvent–Solvent Interactions and Preferential Solvation of 1,1-Diamino-2,2-dinitroethylene in Aqueous Co-solvent Mixtures of N,N-Dimethylformamide and Dimethyl Sulfoxide

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The effects of solvent properties on 1,1-diamino-2,2-dinitroethylene (FOX-7) solubility were investigated from the solubility values in aqueous co-solvent mixtures of N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) in terms of the linear solvation energy relationships with use of mathCAD software. For both aqueous mixtures, the main effect of hydrogen bond basicity was observed based on the solubility variation of FOX-7. The preferential solvation (the difference in composition between the solvation shell of the solute and the bulk composition in a mixture) of FOX-7 in the two aqueous of co-solvent solutions were investigated by using the method of inverse Kirkwood–Buff integrals (IKBI). The values of the preferential solvation parameters (δx1,3) were negative in water-rich mixtures, which are − 3.103×10−2 to − 2.936 × 10−2 for DMF (1) + water (2) mixtures and − 4.470 × 10−2 to − 3.995 × 10−2 for DMSO (1) + water (2) mixtures. However, in the co-solvent compositions ranging from 0.19 or 0.21 to 1 in mole fraction of DMF or DMSO, positive values of δx1,3 were observed. The preference of FOX-7 in water-rich mixtures can be explained based on the higher acidic behavior of FOX-7 molecules, which interact with the proton–acceptor functional groups of DMF and DMSO. KAT-LSER analysis showed that only the hydrogen-bond acceptor basicity of solvents played an important role on the FOX-7 solubility owing to its two amino functional groups. The squared correlation coefficient and F-statistic values are 0.98 and 314 for DMF + water mixture, and 0.96 and 130 for DMSO + water mixture, respectively.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Rubino, J.T.: Cosolvents and cosolvency. In: Swarbrick, J., Boylan, J.C. (eds.) Encyclopedia of Pharmaceutical Technology. Marcel Dekker Inc, New York (1988)

    Google Scholar 

  2. Jouyban, A.: Review of the cosolvency models for predicting solubility of drugs in water–cosolvent mixtures. J. Pharm. Sci. 11, 32–58 (2008)

    CAS  Google Scholar 

  3. Jouyban, A.: Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton (2010)

    Google Scholar 

  4. Marcus, Y.: Preferential solvation in mixed solvents. In: Smith, P.E., Matteoli, E., O’Connell, J.P. (eds.) Fluctuation Theory of Solutions: Applications in Chemistry, Chemical Engineering, and Biophysics. CRC Press, Boca Raton (2013)

    Google Scholar 

  5. Tooski, H.F., Jabbari, M., Farajtabar, A.: Solubility and preferential solvation of the flavonoid naringenin in some aqueous/organic solvent mixtures. J. Solution Chem. 45, 1701–1714 (2016)

    Article  CAS  Google Scholar 

  6. Cárdenas, Z.J., Jiménez, D.M., Delgado, D.R., Almanza, O.A., Jouyban, A., Martínez, F., Acree Jr., W.E.: Solubility and preferential solvation of some n-alkyl-parabens in methanol + water mixtures at 298.15 K. J. Chem. Thermodyn. 108, 26–37 (2017)

    Article  CAS  Google Scholar 

  7. Li, X.B., Cheng, C., Cong, Y., Du, C.B., Zhao, H.K.: Preferential solvation of pioglitazone hydrochloride in some binary co-solvent mixtures according to the inverse Kirkwood–Buff integrals method. J. Chem. Thermodyn. 110, 218–226 (2017)

    Article  CAS  Google Scholar 

  8. Ben-Naim, A.: Preferential solvation in 2-component and in 3-component systems. Pure Appl. Chem. 62, 25–34 (1990)

    Article  CAS  Google Scholar 

  9. Martínez, F., Jouyban, A., Acree Jr., W.E.: Preferential solvation of etoricoxib in some aqueous binary cosolvent mixtures at 298.15 K. Phys. Chem. Liq. 55, 291–303 (2016)

    Article  CAS  Google Scholar 

  10. Marcus, Y.: Solvent Mixtures: Properties and Selective Solvation. Marcel Dekker, New York (2002)

    Google Scholar 

  11. Marcus, Y.: Solubility and solvation in mixed solvent systems. Pure Appl. Chem. 62, 2069–2076 (1990)

    Article  CAS  Google Scholar 

  12. Anniyappan, M., Talawar, M.B., Gore, G.M., Venugopalan, S., Gandhe, B.R.: Synthesis, characterization and thermolysis of 1,1-diamino-2,2-dinitroethylene (FOX-7) and its salts. J. Hazard. Mater. 137B, 812–819 (2006)

    Article  CAS  Google Scholar 

  13. Liu, L., Li, H.Z., Chen, D., Zhou, X.Q., Huang, Q., Yang, H.J.: Solubility of 1,1-diamino-2,2-dinitroethylene in different pure solvents and binary mixtures (dimethyl sulfoxide + water) and (N,N-dimethylformamide + water) at different temperatures. Fluid Phase Equilibr. 460, 95–104 (2018)

    Article  CAS  Google Scholar 

  14. Ahn, J.H., Kim, J.K., Kim, H.S., Kim, E.J., Koo, K.K.: Solubility of 1,1-diamino-2,2-dinitroethylene in N, N-dimethylformamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone. J. Chem. Eng. Data 54, 3259–3260 (2009)

    Article  CAS  Google Scholar 

  15. Vaullerin, M., Espagnacq, A., Morin-Allory, L.: Prediction of explosives impact sensitivity. Propellants Explos. Pyrotech. 23, 237–239 (1998)

    Article  CAS  Google Scholar 

  16. Oxley, J., Smith, J., Buco, R., Huang, J.: A study of reduced-sensitivity RDX. J. Energ. Mater. 25, 141–160 (2007)

    Article  CAS  Google Scholar 

  17. Stephen, H., Stephen, T.: Solubility of Inorganic and Organic Compounds. Pergamon, Oxford (1979)

    Google Scholar 

  18. Taft, R.W., Abboud, J.L.M., Kamlet, M.I., Abraham, M.H.: Linear solvation energy relations. J. Solution Chem. 14, 153–186 (1985)

    Article  CAS  Google Scholar 

  19. Carr, P.W.: Solvatochromism, linear solvation energy relationships, and chromatography. Microchem. J. 48, 4–28 (1993)

    Article  CAS  Google Scholar 

  20. Kamlet, M.J., Abboud, J.L.M., Taft, R.W.: An examination of linear solvation energy relationships. Prog. Phys. Org. Chem. 13, 485–630 (1980)

    Google Scholar 

  21. Kamlet, M.J., Doherty, R.M., Abboud, J.L.M., Abraham, M.H., Taft, R.W.: Linear solvation energy relationships: 36. Molecular properties governing solubilities of organic nonelectrolytes in water. J. Pharm. Sci. 75, 338–349 (1986)

    Article  CAS  PubMed  Google Scholar 

  22. Marcus, Y.: The Properties of Solvents. Wiley, Chichester (1998)

    Google Scholar 

  23. Marcus, Y.: The use of chemical probes for the characterization of solvent mixtures. Part 2. Aqueous mixtures. J. Chem. Soc. Perkin Trans. 2, 1751–1758 (1994)

    Article  Google Scholar 

  24. Hansen, C.M.: Hansen Solubility Parameters: A User’s Handbook. CRC Press, Boca Raton (2007)

    Book  Google Scholar 

  25. Bernal-García, J.M., Guzmán-López, A., Cabrales-Torres, A., Estrada-Baltazar, A., Iglesias-Silva, G.A.: Densities and viscosities of (N,N-dimethylformamide + water) at atmospheric pressure from (283.15 to 353.15) K. J. Chem. Eng. Data 53, 1024–1027 (2008)

    Article  CAS  Google Scholar 

  26. Grande, M.D.C., Juliá, J.A., García, M., Marschoff, C.M.: On the density and viscosity of (water + dimethylsulphoxide) binary mixtures. J. Chem. Thermodyn. 39, 1049–1056 (2007)

    Article  CAS  Google Scholar 

  27. Kamlet, M.J., Taft, R.W.: The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 98, 377–383 (1976)

    Article  CAS  Google Scholar 

  28. Taft, R.W., Kamlet, M.J.: The solvatochromic comparison method. 2. The alpha-scale of solvent hydrogen-bond donor (HBD) acidities. J. Am. Chem. Soc. 98, 2886–2894 (1976)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project number 41877118); Natural Science Foundation of Jiangsu Province of China (project number BK20181479) and Natural Science Foundation of the Jiangsu Higher Education Institutions of China (project number 17KJB610013).

Author information

Authors and Affiliations

  1. School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng, 224002, Jiangsu, People’s Republic of China

    Wanxin Li, Nan Wang, Zhongtang Liu & Zhenghao Fei

  2. Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran

    Ali Farajtabar

  3. College of Chemistry & Chemical Engineering, YangZhou University, YangZhou, 225002, Jiangsu, People’s Republic of China

    Hongkun Zhao

Authors
  1. Wanxin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ali Farajtabar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhongtang Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhenghao Fei
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hongkun Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hongkun Zhao.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, W., Wang, N., Farajtabar, A. et al. Solute–Solvent and Solvent–Solvent Interactions and Preferential Solvation of 1,1-Diamino-2,2-dinitroethylene in Aqueous Co-solvent Mixtures of N,N-Dimethylformamide and Dimethyl Sulfoxide. J Solution Chem 48, 732–747 (2019). https://doi.org/10.1007/s10953-019-00878-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-019-00878-y

Keywords

Search

Navigation