Skip to main content
SpringerLink
Log in

Proton transfer from H2O to p-substituted anilide anion: can the size of water cluster influence the N-⋅⋅⋅H–OH→N–H⋅⋅⋅OH- switching

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

Abstract

The effects of the H2O cluster size and the substituent (X=H, Me, OMe, CHO, NO and NO2) in the para position of anilide ion on the HN-⋅⋅⋅H–OH→HN–H⋅⋅⋅OH- switching were investigated by means of B3LYP and MP2 methods. The changes in the H-bond strength due to variation of the substituent and H2O cluster size were well monitored by changes in the interaction energy, structural parameter, electron density topology, natural charge, charge transfer and percentage of p-character of N atom in the C–N bond. The HN-⋅⋅⋅H–OH→HN–H⋅⋅⋅OH- switching was enhanced by an increase in the extent of solvation and the insertion of the electron-donating substituents in the para position. The results demonstrate that the strength of the HN-∙∙∙HO H-bond increases and that of NH∙∙∙OH- H-bond decreases by electron-donating substituents. The reverse situations were found for electron-accepting substituents.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Chart 1
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Cha Y, Murray CJ, Klinman JP (1989) Science 243:1325–1330

    Article  CAS  Google Scholar 

  2. Paddock ML, Rongey SH, Feher G, Okamura MY (1989) Proc Natl Acad Sci USA 86:6602–6606

    Article  CAS  Google Scholar 

  3. Bell RL, Truong TN (1994) J Chem Phys 101:10442–10451

    Article  CAS  Google Scholar 

  4. Kim TG, Lee SI, Jiang DJ, Kim YI (1995) J Phys Chem 99:12698–12700

    Article  CAS  Google Scholar 

  5. Podolyan Y, Gorb L, Leszczynski J (2002) J Phys Chem A 106:12103–12109

    Article  CAS  Google Scholar 

  6. Hu X, Li H, Liang W, Han S (2004) J Phys Chem B 108:12999–13007

    Article  CAS  Google Scholar 

  7. Kim Y (1998) J Phys Chem A 102:3025–3036

    Article  CAS  Google Scholar 

  8. Ahn DS, Lee S, Kim B (2004) Chem Phys Lett 390:384–388

    Article  CAS  Google Scholar 

  9. Meot-Ner (Mautner) M (2005) Chem Rev 105:213–284, and references cited therein

    Article  Google Scholar 

  10. Szatyłowicz H, Krygowski TM, Zachara-Horeglad JE (2007) J Chem Inf Model 47:875–886

    Article  Google Scholar 

  11. Szatyłowicz H, Krygowski TM, Panek JJ, Jezierska A (2008) J Phys Chem A 112:9895–9905

    Article  Google Scholar 

  12. Szatyłowicz H, Krygowski TM, Jezierska A, Panek JJ (2009) J Phys Chem A 113:5800–5805

    Article  Google Scholar 

  13. Wolf I, Shapira A, Giniger R, Miller Y, Gerber RB, Cheshnovsky O (2008) Angew Chem Int Ed 47:6272–6274

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  15. Granovsky AA, PC GAMESS Version 7.1. <http://classic.chem.msu.su/gran/gamess/index.html>

  16. Biegler-König FF, Schönbohm J, Bayles D (2001) AIM2000-A program to analyze and visualize atoms in molecules. J Comp Chem 22:545–559

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

  19. Krygowski TM, Szatyłowicz H (2006) J Phys Chem A 110:7232–7236

    Article  CAS  Google Scholar 

  20. Koch U, Popelier PLA (1995) J Phys Chem 99:9747–9754

    Article  CAS  Google Scholar 

  21. Popelier PLA (1998) J Phys Chem A 102:1873–1878

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Guilan, Namjoh Street, P.O. Box 41335–1914, Rasht, Iran

    Hossein Roohi

  2. Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, Zahedan, Iran

    Behnaz Moghadam

Authors
  1. Hossein Roohi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Behnaz Moghadam
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hossein Roohi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Roohi, H., Moghadam, B. Proton transfer from H2O to p-substituted anilide anion: can the size of water cluster influence the N-⋅⋅⋅H–OH→N–H⋅⋅⋅OH- switching. J Mol Model 18, 1313–1324 (2012). https://doi.org/10.1007/s00894-011-1156-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00894-011-1156-7

Keywords

Search

Navigation