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


Reference:

Katif, N., Harries, R. A., Kelly, A. M., Fossey, J. S., James, T. D. and Marken, F., 2009. Boronic acid-facilitated α-hydroxy-carboxylate anion transfer at liquid/liquid electrode systems: the EICrev mechanism. Journal of Solid State Electrochemistry, 13 (10), pp. 1475-1482.

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Official URL:

http://dx.doi.org/10.1007/s10008-008-0709-x

Abstract

The transfer of the alpha-hydroxy-carboxylates of glycolic, lactic, mandelic and gluconic acid from the aqueous electrolyte phase into an organic 4-(3-phenyl-propyl)-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 alpha-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.

Details

Item Type Articles
CreatorsKatif, N., Harries, R. A., Kelly, A. M., Fossey, J. S., James, T. D. and Marken, F.
DOI10.1007/s10008-008-0709-x
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code24577

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