Advertisement

Journal of Solid State Electrochemistry

, Volume 13, Issue 10, pp 1475–1482 | Cite as

Boronic acid-facilitated α-hydroxy-carboxylate anion transfer at liquid/liquid electrode systems: the EICrev mechanism

  • Najoua Katif
  • Rachel A. Harries
  • Andrew M. Kelly
  • John S. Fossey
  • Tony D. James
  • Frank MarkenEmail author
Original Paper

Abstract

The transfer of the α-hydroxy-carboxylates of glycolic, lactic, mandelic and gluconic acid from the aqueous electrolyte phase into an organic 4-(3-phenylpropyl)-pyridine (PPP) phase is studied at a triple-phase boundary electrode system. The tetraphenylporphyrinato complex MnTPP dissolved in PPP is employed to drive the anion transfer reaction and naphthalene-2-boronic acid (NBA) is employed as a facilitator. In the absence of a facilitator, the ability of α-hydroxy-carboxylates to transfer into the organic phase improves, consistent with hydrophobicity considerations giving relative transfer potentials (for aqueous 0.1 M solution) of gluconate>glycolate>lactate>mandelate. In the presence of NBA, a shift of the reversible transfer potential to more negative values is indicating fast reversible binding (the mechanism for the electrode process is EICrev) and the binding constants are determined as K glycolate = 2 M−1, K mandelate = 60 M−1, K lactate = 130 M−1 and K gluconate = 2,000 M−1. The surprisingly strong interaction for gluconate is rationalised based on secondary interactions between the gluconate anion and NBA.

Keywords

Boronic acid Carbohydrate α-Hydroxy carboxylic acid Voltammetry Liquid/liquid interface Electrocatalysis Sensors 

Notes

Acknowledgement

NK thanks the RSC and EPSRC for the award of an Analytical Studentship. JSF thanks the Leverhulme Trust (F/00/351/P) and the Royal Society Research Grants Scheme (2007/R2). Financial support for AMK from the Leverhulme Trust (F/00351/R) is gratefully acknowledged.

References

  1. 1.
    Bard AJ, Faulkner LR (2001) Electrochemical methods, 2nd edn. Wiley, New York, p 471Google Scholar
  2. 2.
    Scholz F, Gulaboski R (2005) ChemPhysChem 6:16. doi: 10.1002/cphc.200400248 CrossRefGoogle Scholar
  3. 3.
    Liu B, Mirkin MV (2000) Electroanalysis 12:1433 doi: 10.1002/1521-4109(200012)12:18<1433::AID-ELAN1433>3.0.CO;2-2 CrossRefGoogle Scholar
  4. 4.
    Reymond F, Girault HH (2000) Electrochemistry at liquid–liquid interfaces. In: Meyers RA (ed) Encyclopedia of analytical chemistry. Wiley, New YorkGoogle Scholar
  5. 5.
    Banks CE, Davies TJ, Evans RG, Hignett G, Wain AJ, Lawrence NS, Wadhawan JD, Marken F, Compton RG (2003) Phys Chem Chem Phys 5:4053. doi: 10.1039/b307326m CrossRefGoogle Scholar
  6. 6.
    Scholz F, Schröder U, Gulaboski R (2005) Electrochemistry of immobilized particles and droplets. Springer, BerlinGoogle Scholar
  7. 7.
    Marken F, Webster RD, Bull SD, Davies SG (1997) J Electroanal Chem 437:209. doi: 10.1016/S0022-0728(97)00398-7 CrossRefGoogle Scholar
  8. 8.
    Dwyer P, Cunnane VJ (2005) J Electroanal Chem 581:16. doi: 10.1016/j.jelechem.2005.03.043 CrossRefGoogle Scholar
  9. 9.
    Guo SX, Unwin PR, Whitworth AL, Zhang J (2004) Prog React Kinet Mech 29:43Google Scholar
  10. 10.
    Nishi N, Murakami H, Imakura S, Kakiuchi T (2006) Anal Chem 78:5805. doi: 10.1021/ac060797y CrossRefGoogle Scholar
  11. 11.
    Dryfe RAW (2006) Phys Chem Chem Phys 8:1869. doi: 10.1039/b518018j CrossRefGoogle Scholar
  12. 12.
    Dassie SA (2005) J Electroanal Chem 585:256. doi: 10.1016/j.jelechem.2005.09.001 CrossRefGoogle Scholar
  13. 13.
    Fujita N, Shinkai S, James TD (2008) Chemistry 3:1076. doi: 10.1002/asia.200800069 Google Scholar
  14. 14.
    James TD, Sandanayake KARS, Shinkai S (1996) Angew Chem Int Ed Engl 35:1910. doi: 10.1002/anie.199619101 CrossRefGoogle Scholar
  15. 15.
    James TD, Phillips MD, Shinkai S (2006) Boronic acids in saccharide recognition. The Royal Society of Chemistry, CambridgeGoogle Scholar
  16. 16.
    Houston TA, Levonis SM, Kiefel MJ (2007) Aust J Chem 60:811. doi: 10.1071/CH07222 CrossRefGoogle Scholar
  17. 17.
    Zhao J, Fyles TM, James TD (2004) Angew Chem Int Ed Engl 43:3461. doi: 10.1002/anie.200454033 CrossRefGoogle Scholar
  18. 18.
    Zhao J, Davidson MG, Mahon MF, Kociok-Köhn G, James TD (2004) J Am Chem Soc 126:16179. doi: 10.1021/ja046289s CrossRefGoogle Scholar
  19. 19.
    Rogowska P, Cyranski MK, Sporzynski A, Ciesielski A (2006) Tetrahedron Lett 47:1389. doi: 10.1016/j.tetlet.2005.12.105 CrossRefGoogle Scholar
  20. 20.
    Rhlalou T, Ferhat M, Frouji MA, Langevin D, Metayer M, Verchere JF (2000) J Membr Sci 168:63. doi: 10.1016/S0376-7388(99)00301-4 CrossRefGoogle Scholar
  21. 21.
    Bonne MJ, Reynolds C, Yates S, Shul G, Niedziolka J, Opallo M, Marken F (2006) New J Chem 30:327. doi: 10.1039/b514348a CrossRefGoogle Scholar
  22. 22.
    Scholz F, Gulaboski R, Caban K (2003) Electrochem Commun 5:929. doi: 10.1016/j.elecom.2003.09.005 CrossRefGoogle Scholar
  23. 23.
    Schröder U, Wadhawan J, Evans RG, Compton RG, Wood B, Walton DJ, France RR, Marken F, Page PCB, Hayman CM (2002) J Phys Chem B 106:8697. doi: 10.1021/jp0146059 CrossRefGoogle Scholar
  24. 24.
    Marken F, McKenzie KJ, Shul G, Opallo M (2005) Faraday Discuss 129:219. doi: 10.1039/b405365f CrossRefGoogle Scholar
  25. 25.
    Gulaboski R, Riedl K, Scholz F (2003) Phys Chem Chem Phys 5:1284. doi: 10.1039/b210356g CrossRefGoogle Scholar
  26. 26.
    MacDonald SM, Opallo M, Klamt A, Eckert F, Marken F (2008) Phys Chem Chem Phys 10:3925. doi: 10.1039/b803582b CrossRefGoogle Scholar
  27. 27.
    Katif N, MacDonald SM, Kelly AM, Galbraith E, James TD, Lubben AT, Opallo M, Marken F (2008) Electroanalysis 20:469. doi: 10.1002/elan.200704127 CrossRefGoogle Scholar
  28. 28.
    Scholz F, Schröder U, Gulaboski R (2005) Electrochemistry of immobilized particles and droplets. Springer, Berlin, p 214Google Scholar
  29. 29.
    MacDonald SM, Fletcher PDI, Cui ZG, Opallo M, Chen JY, Marken F (2007) Electrochim Acta 53:1175. doi: 10.1016/j.electacta.2007.01.072 CrossRefGoogle Scholar
  30. 30.
    Lide DR (ed) (1962) CRC handbook of chemistry and physics. CRC, FloridaGoogle Scholar
  31. 31.
    Zhang Z, Gibson P, Clark SB, Tian G, Zanonato PL, Rao L (2007) J Solution Chem 36:1187. doi: 10.1007/s10953-007-9182-x CrossRefGoogle Scholar
  32. 32.
    Zhao JZ, James TD (2005) Chem Commun (Camb) 1889–1891Google Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Najoua Katif
    • 1
  • Rachel A. Harries
    • 1
  • Andrew M. Kelly
    • 1
  • John S. Fossey
    • 1
  • Tony D. James
    • 1
  • Frank Marken
    • 1
    Email author
  1. 1.Department of ChemistryUniversity of BathBathUK

Personalised recommendations