Skip to main content
SpringerLink
Log in

Kinetic study of the oxovanadium(IV)–salen-catalyzed H2O2 oxidation of phenols

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

The oxovanadium(IV)–salen-catalyzed H2O2 oxidation of phenols gives o-catechol and hydroquinone as the reaction products. The reaction follows Michaelis–Menten-type kinetics, and the rate is accelerated by electron-donating substituents on both the substrate and the salen ligand. This peculiar substituent effect is accounted for in terms of bond formation between peroxo group of the oxidant and the benzene ring of the substrate in the transition state. A suitable mechanism for the reaction is proposed.

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
Fig. 7
Scheme 1

Similar content being viewed by others

References

  1. Monteir B (1989) In: Harborne JB (ed) Methods in plant biochemistry. Academic Press, London

    Google Scholar 

  2. Kuss-Petermann M, Wolf H, Stalke D, Wenger OS (2012) J Am Chem Soc 134:12844–12854

    Article  CAS  Google Scholar 

  3. Asami K, Takashina A, Kobayashi M, Iwatsuki S, Yajima T, Kochem A, van Gastel M, Tani F, Kohzuma T, Thomas F, Shimazaki Y (2014) Dalton Trans 43:2283–2293

    Article  CAS  Google Scholar 

  4. Lavis LD, Raines RT (2014) ACS Chem Biol 9:855–866

    Article  CAS  Google Scholar 

  5. Song N, Stanbury DM (2012) Inorg Chem 51:4909–4911

    Article  CAS  Google Scholar 

  6. Puzari A, Baruah JB (2000) J Org Chem 65:2344–2349

    Article  CAS  Google Scholar 

  7. Kurahashi T, Oda K, Sugimoto M, Ogura T, Fujii H (2006) Inorg Chem 45:7709–7721

    Article  CAS  Google Scholar 

  8. Huang H, Sommerfeld D, Dunn BC, Eyring EM, Lloyd CR (2001) J Phys Chem A 105:3536–3541

    Article  CAS  Google Scholar 

  9. Colclough M, Smith JRL (1994) J Chem Soc Perkin Trans 2:1139–1149

    Article  Google Scholar 

  10. Xie J-Q, Li J-Z, Meng X-G, Hu C-W, Zeng X-C, Li S-X (2004) Trans Met Chem 29:388–393

    Article  CAS  Google Scholar 

  11. Jeyaseeli AMI, Rajagopal S (2009) J Mol Catal A: Chem 309:103–110

    Article  Google Scholar 

  12. Sivasubramanian VK, Ganesan M, Rajagopal S, Ramaraj R (2002) J Org Chem 67:1506–1514

    Article  CAS  Google Scholar 

  13. Aslam AM, Rajagopal S, Vairamani M, Ravikumar M (2011) Trans Met Chem 36:751–759

    Article  CAS  Google Scholar 

  14. Venkataramanan NS, Kuppuraj G, Rajagopal S (2005) Coord Chem Rev 249:1249–1268

    Article  CAS  Google Scholar 

  15. Kurahashi T, Kikuchi A, Shiro Y, Hada M, Fujii H (2010) Inorg Chem 49:6664–6672

    Article  CAS  Google Scholar 

  16. Rehder D, Santonin G, Licini GM, Schulzke C, Meier B (2003) Coord Chem Rev 237:53–63

    Article  CAS  Google Scholar 

  17. Shechter Y, Goldwaser I, Mironchik M, Fridkin M, Gefel D (2003) Coord Chem Rev 237:3–11

    Article  CAS  Google Scholar 

  18. Eady RR (2003) Coord Chem Rev 237:23–30

    Article  CAS  Google Scholar 

  19. Thompson KH, McNeill JH, Orvig C (1999) Chem Rev 99:2561–2572

    Article  CAS  Google Scholar 

  20. Maurelli S, Berlier G, Chiesa M, Musso F, Cora F (2014) J Phys Chem C 118:19879–19888

    Article  CAS  Google Scholar 

  21. Hendaway AME, Fayed AM, Mostafa MR (2011) Trans Met Chem 36:351–361

    Article  Google Scholar 

  22. Rayati S, Ghaemi A, Sadeghzadeh N (2010) Catal Commun 11:792–796

    Article  CAS  Google Scholar 

  23. Maurya MR, Kumar A (2006) J Mol Catal A: Chem 250:190–198

    Article  CAS  Google Scholar 

  24. Joseph JK, Singhal S, Jain SL, Sivakumaran R, Kumar B, Sain B (2009) Catal Today 141:211–214

    Article  CAS  Google Scholar 

  25. Zhang J, Tang Y, Li GY, Hu C (2005) Appl Catal A Gen 278:251–261

    Article  CAS  Google Scholar 

  26. Maurya MR, Agarwal S, Bader C, Ebel M, Rehder D (2005) Dalton Trans 537–544

  27. Maurya MR, Kumar A, Manikandan P, Chand S (2004) Appl Catal A Gen 277:45–53

    Article  CAS  Google Scholar 

  28. Boghaei DM, Mohebi S (2002) J Mol Catal A: Chem 179:41–51

    Article  CAS  Google Scholar 

  29. Sankareswari VG, Vinod D, Mahalakshmi A, Alamelu M, Kumaresan G, Ramaraj R, Rajagopal S (2014) Dalton Trans 43:3260–3272

    Article  Google Scholar 

  30. Adao P, Pessoa JC, Henriques RT, Kuzenetsov ML, Avecilla F, Maurya MR, Kumar U, Correia I (2009) Inorg Chem 48:3542–3561

    Article  CAS  Google Scholar 

  31. Conte V, Coletti A, Floris B, Licini G, Zonta C (2011) Coord Chem Rev 255:2165–2177

    Article  CAS  Google Scholar 

  32. Litwinieko G, Ingold KU (2007) Acc Chem Res 40:222–230

    Article  Google Scholar 

  33. Rayati S, Koliaei M, Ashouri F, Mohebbi S, Wojtczak A, Kozakiewicz A (2008) Appl Catal A Gen 346:65–71

    Article  CAS  Google Scholar 

  34. Zhang J, Tang Y, Xie J-Q, Li J-Z, Zeng W, Hu C-W (2005) J Serb Chem Soc 70:1137–1146

    Article  CAS  Google Scholar 

  35. Maurya MR, Kumar U, Manikandan P (2007) Eur J Inorg Chem 2303–2314

Download references

Acknowledgments

Prof. S.R thanks UGC, New Delhi, for sanctioning UGC-BSR Faculty Fellowship. A.M thanks the UGC, New Delhi, and the Management of V. O. C. College, Tuticorin, for sanctioning permission to avail the benefits of Faculty Development Programme (FDP). A.R is the recipient of UGC Meritorious fellowship under the Basic Scientific Research (BSR) Scheme.

Author information

Authors and Affiliations

  1. Department of Chemistry, V.O. Chidambaram College, Tuticorin, 628 008, India

    Alagarsamy Mathavan

  2. School of Chemistry, Madurai Kamaraj University, Madurai, 625 021, India

    Alagarsamy Mathavan, Arumugam Ramdass & Seenivasan Rajagopal

Authors
  1. Alagarsamy Mathavan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arumugam Ramdass
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Seenivasan Rajagopal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Seenivasan Rajagopal.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1887 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mathavan, A., Ramdass, A. & Rajagopal, S. Kinetic study of the oxovanadium(IV)–salen-catalyzed H2O2 oxidation of phenols. Transition Met Chem 40, 355–362 (2015). https://doi.org/10.1007/s11243-015-9924-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-015-9924-3

Keywords

Search

Navigation