| Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S. | |
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MedLine Citation:
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PMID: 22283713 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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In this work, the reaction between phenylboronic acid and the diol-containing, fluorescent dye Alizarin Red S (ARS) was probed. Fluorescence titrations, (11)B NMR measurements, and both pre- and steady-state kinetic experiments were used for the characterization of this reaction over a large pH range (4-10.5). It was shown that ARS preferentially reacted with the boronic (neutral, trigonal) form of phenylboronic acid; however, the boronate (anionic, tetrahedral) form was also reactive. All in all, four reactant species were implicated in the formation of four different adduct species. The rate of a given adduct formation depended on the combination of the solution pH and the pK(a)'s of both ARS and the arylboronic acid. The reaction was found to proceed in two distinct kinetic steps with the products and starting materials in facile exchange. In addition, the elucidation of the mechanism indicated the presence of two fluorescent products with the structure of the major contributor differing from what had been cited in the literature. |
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Authors:
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John W Tomsho; Stephen J Benkovic |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-1-13 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2012 Jan |
Date Detail:
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Created Date: 2012-1-30 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Chemistry, The Pennsylvania State University , 414 Wartik Laboratory, University Park, Pennsylvania 16802, United States. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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