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Issue 12, 1988
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Simultaneous proton removal from open and closed forms of hydrogen-bonded phenylazoresorcinols by general bases

Abstract

The kinetics of equilibration between the monoanions and dianions of substituted phenylazoresorcinols has been studied in buffered 70%(v/v) Me2SO–H2O. Kinetic terms arising from proton removal by buffer base and hydroxide ion from hydrogen-bonded and non-hydrogen-bonded forms of the monoanions have been observed. The rate coefficients (Bkc) for proton removal from the hydrogen-bonded forms are several orders of magnitude below those for reaction of the open forms and depend on the strength of the catalysing base; Bkc for hydroxide ion is ca. 70-fold higher than Bkc for indazole ion. For reaction of 2-methyl-4-(4-nitrophenylazo)resorcinol with indazole ion, the kinetic solvent isotope effect is negligibly small Bkc(H2O)/Bkc(D2O)ca. 1.2.

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Article type: Paper
DOI: 10.1039/P29880002123
J. Chem. Soc., Perkin Trans. 2, 1988, 2123-2127

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    Simultaneous proton removal from open and closed forms of hydrogen-bonded phenylazoresorcinols by general bases

    N. E. Briffett, F. Hibbert and R. J. Sellens, J. Chem. Soc., Perkin Trans. 2, 1988, 2123
    DOI: 10.1039/P29880002123

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