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


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.


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



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.


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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

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