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Issue 83, 2015
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Kinetics of the oxidation of isoniazid with the hypochlorite ion

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Abstract

The stoichiometry and kinetics of the reaction between isoniazid (isonicotinic hydrazide, INH) and the hypochlorite ion was studied in a basic aqueous medium (pH > 10) by spectrophotometric, hydrogen-1 nuclear magnetic resonance, electrospray mass spectrometric and stopped-flow methods. At oxidant excess, the sole organic product was confirmed to be isonicotinic acid. At isoniazid excess, a coupled condensation product formed from isoniazid and isonicotinic acid was also detected in relatively high amounts. The stoichiometric ratio of the two reactants (INH/OCl) was 0.46 or 0.67 depending on which of the reagents was in excess initially. Under all conditions, the rate determining step of the overall reaction was confirmed to be the rapid bimolecular reaction between the neutral from of isoniazid and the anionic hypochlorite ion. The second order rate constant of the process was estimated to be (3.4 ± 0.7) × 104 M−1 s−1 at 25.0 °C.

Graphical abstract: Kinetics of the oxidation of isoniazid with the hypochlorite ion

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Publication details

The article was received on 10 Jul 2015, accepted on 30 Jul 2015 and first published on 30 Jul 2015


Article type: Paper
DOI: 10.1039/C5RA13540K
RSC Adv., 2015,5, 67500-67508

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    Kinetics of the oxidation of isoniazid with the hypochlorite ion

    V. Bogdándi, G. Lente and I. Fábián, RSC Adv., 2015, 5, 67500
    DOI: 10.1039/C5RA13540K

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