A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene

Nick Backstrom, C. I F Watt

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The behaviour of solutions of the sodium salt of 4-(2,4-dinitrophenyl)pentanoic acid in D2O is readily monitored by 1H NMR spectroscopy. In the presence of excess NaOD, these show exchange of hydrogen at the 3-position of the benzene ring with kOD = 1.23(0.03) × 10-4 M-1 s-1 at 25 °C. Rates of exchange using solutions with triethylamine buffers show no dependence on buffer concentration and an estimate of the acid dissociation constant, pKa ≈ 29.3, of the dinitrobenzene is made. Under the conditions, there is no detectable exchange at the benzylic position. © 2009 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)3234-3236
    Number of pages2
    JournalTetrahedron Letters
    Volume50
    Issue number26
    DOIs
    Publication statusPublished - 1 Jul 2009

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