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Protonation and solvent extraction of N-p-tolylbenzohydroxamic acid in hydrochloric acid medium



Protonation and solvent extraction of N-p-tolylbenzohydroxamic acid in hydrochloric acid medium



Talanta 38(9): 1015-1018



the protonation of N-p-tolylbenzohydroxamic acid (p-TBHA) in aqueous hydrochloric acid has been investigated by determination of its distribution between cyclohexane and hydrochloric acid. The pK(a) value found was - 2.30 +/- 0.02 at 30 degrees . The solubility of p-TBHA as a function of hydrochloric acid concentration has also been determined. At lower acid concentrations the solubility decreases owing to a salting-out effect, whereas at higher concentrations it increases because of formation of the more hydrophilic protonated species and a salting-in effect. Intramolecular hydrogen-bonding observed in p-TBHA provides evidence for protonation of the nitrogen atom.

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Accession: 055260938

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PMID: 18965253

DOI: 10.1016/0039-9140(91)80318-t


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