Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution

Michael G. Chudzinski A , Yuechuan Chi A and Mark S. Taylor A B

A Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.

B Corresponding author. Email: mtaylor@chem.utoronto.ca

Australian Journal of Chemistry 64(11) 1466-1469 http://dx.doi.org/10.1071/CH11294
Submitted: 16 July 2011  Accepted: 15 August 2011   Published: 16 November 2011

Abstract

Association constants between diphenylborinic acid and representative analytes capable of reversible two-point covalent binding (diols, catechols, and hydroxy acids) were determined using an indicator-displacement assay. Unlike boronic acids, which have been studied in great detail as receptors for diols and related compounds, borinic acids have effectively been ignored as candidates for such applications. The results of this study indicate that diphenylborinic acid displays high affinity for certain analytes of this type in aqueous solution. Of particular interest are differences between the selectivity of the borinic acid and that of a boronic acid of similar pKa towards the series of analytes studied: the borinic acid displays an unusually high level of discrimination for catechols over carbohydrates. The distinct selectivity observed, and the unique opportunities for steric and electronic tuning of diarylborinic acids, suggest that these compounds hold significant potential for applications in aqueous-phase molecular recognition.

Graphical Abstract Image


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