Skip to main content
SpringerLink
Log in

Ground- and excited-state stability of the conformers of 3,5-dinitrocatechol and its complexes with W(VI) and V(V): combined theoretical and experimental study

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

Abstract

We performed a theoretical and experimental study of the (photo)stability of 3,5-dinitrocatechol (DNC) and its complexes with W(VI) and V(V). The investigation showed that irradiation of DNC is accompanied by a parallel proton migration from the hydroxy group to the neighboring NO2 group, which results in a large Stokes shift of the absorption and emission bands. It was found that W(VI) forms a more stable 1:2 complex than V(V). The complex is stable even under UV irradiation. The most stable WVI(DNC)2 conformer is comprised of two mutually perpendicular DNC molecules as ligands.

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
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Gavazov KB (2012) Acta Chim Slov 59:1–17

    CAS  Google Scholar 

  2. Vidgren J, Svensson LA, Liljas A (1994) Nature 368:354–358

    Article  CAS  Google Scholar 

  3. Palma PN, Rodrigues ML, Archer M, Bonifácio MJ, Loureiro AI, Learmonth DA, Carrondo MA, Soares-da-Silva P (2006) Mol Pharmacol 70:143–153

    CAS  Google Scholar 

  4. Palma PN, Bonifácio MJ, Loureiro AI, Wright LC, Learmonth DA, Soares-da-Silva P (2003) Drug Metab Dispos 31:250–258

    Article  CAS  Google Scholar 

  5. Lautala P, Kivimaa M, Salomies H, Elovaara E, Taskinen J (1997) Pharm Res 14:1444–1448

    Article  CAS  Google Scholar 

  6. Rutherford K, Le Trong I, Stenkamp RE, Parson WW (2008) J Mol Biol 380:120–130

    Article  CAS  Google Scholar 

  7. Kitanovski Z, Grgić I, Vermeylen R, Claeys M, Maenhaut W (2012) J Chromatogr A 1268:35–43

    Article  CAS  Google Scholar 

  8. Iinuma Y, Böge O, Gräfe R, Herrmann H (2010) Environ Sci Technol 44:8453–8459

    Article  CAS  Google Scholar 

  9. Pakala S, Gorla P, Pinjari A, Krovidi R, Baru R, Yanamandra M, Merrick M, Siddavattam D (2007) Appl Microbiol Biol 73:1452–1462

    Article  CAS  Google Scholar 

  10. Haigler BE, Spain JC (1991) Appl Environ Microbiol 57:3156–3162

    CAS  Google Scholar 

  11. Haigler BE, Suen WC, Spain JC (1996) J Bacteriol 178:6019–6024

    CAS  Google Scholar 

  12. Ju K-S, Parales RE (2010) Microbiol Mol Biol Rev 74:250–272

    Article  CAS  Google Scholar 

  13. Liu Y, Wang D, Sun B, Zhu X (2010) J Hazard Mater 181:1010–1015

    Article  CAS  Google Scholar 

  14. Chaliha S, Bhattacharyya KG, Paul P (2008) J Chem Technol Biotechnol 83:1353–1363

    Article  CAS  Google Scholar 

  15. Schulte-Frohlinde D, Reutebuch G, von Sonntag C (1973) Int J Radiat Phys Chem 5:331–342

    Article  CAS  Google Scholar 

  16. Poluektova EN, Shitareva GG (1972) Zh Anal Khim 27:1301–1304

    CAS  Google Scholar 

  17. Marczenko Z, Lobinski R (1988) Talanta 35:1001–1004

    Article  CAS  Google Scholar 

  18. Lobinski R, Marczenko Z (1988) Anal Sci 4:629–35

    Article  CAS  Google Scholar 

  19. Lobinski R, Marczenko Z (1990) Microchem J 42:197–205

    Article  CAS  Google Scholar 

  20. Marczenko Z, Balcerzak M (2007) Metod’y spektrofotometrii v UF I vidimoj oblastyakh v neorganicheskom analize. Laboratoriya znanij, Binom

    Google Scholar 

  21. Dimitrov A, Lekova V, Gavazov K, Boyanov B (2007) J Anal Chem 62:122–125

    Article  CAS  Google Scholar 

  22. Racheva P, Gavazov K, Lekova V, Dimitrov A (2008) J Iran Chem Res 1:113–121

    Google Scholar 

  23. Lekova V, Racheva P, Stojnova K, Dimitrov A, Gavazov K (2010) Chemija 21:106–111

    CAS  Google Scholar 

  24. Racheva PV, Gavazov KB, Lekova VD, Dimitrov AN (2010) J Anal Chem 65:21–25

    Article  CAS  Google Scholar 

  25. Sommer L, Ackermann G, Burns DT, Savvin SB (1990) Pure Appl Chem 62:2147–2166

    CAS  Google Scholar 

  26. Cornard J-P, Rasmiwetti, Merlin J-C (2005) Chem Phys 309:239–249

    Article  CAS  Google Scholar 

  27. Cornard J-P, Lapouge C, Merlin J-C (2007) Chem Phys 340:273–282

    Article  CAS  Google Scholar 

  28. Riley KE, Pitonak M, Jurecka P, Hobza P (2010) Chem Rev 110:5023–5063

    Article  CAS  Google Scholar 

  29. Frisch MT et al. (2004) Gaussian 03, Revision D.01. Gaussian, Wallingford

  30. Hättig C, Weigend F (2000) J Chem Phys 113:5154–5161

    Article  Google Scholar 

  31. Hammond GS (1955) J Am Chem Soc 77:334–338

    Article  CAS  Google Scholar 

  32. Leffler JE (1953) Science 117:340–341

    Article  CAS  Google Scholar 

  33. Taylor MJC, Staden JF (1994) Analyst 119:1263–1276

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank Prof. Petko Ivanov [Institute of Organic Chemistry, Bulgarian Academy of Sciences (BAS)] for the given computational quota and technical support for the CC2 calculations (Linux-cluster MADARA), project RNF01/0110. We thank also Associate Prof. Dr Timcheva and Assistant Professor Nadya Kyuchukova (Institute of Organic chemistry, BAS) for registration of the fluorescence spectra, and Mrs. Neda Danova (University of Plovdiv, Dept. Analytical Chemistry) for experimental registration of the UV spectra.

Author information

Authors and Affiliations

  1. Faculty of Chemistry, University of Plovdiv, 4000, Plovdiv, Bulgaria

    V. B. Delchev & K. B. Gavazov

  2. Department Inorganic and Physical Chemistry, University of Food Technologies, 4002, Plovdiv, Bulgaria

    I. G. Shterev

Authors
  1. V. B. Delchev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. B. Gavazov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. G. Shterev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. B. Delchev.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(DOC 1817 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Delchev, V.B., Gavazov, K.B. & Shterev, I.G. Ground- and excited-state stability of the conformers of 3,5-dinitrocatechol and its complexes with W(VI) and V(V): combined theoretical and experimental study. J Mol Model 20, 2549 (2014). https://doi.org/10.1007/s00894-014-2549-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00894-014-2549-1

Keywords

Search

Navigation