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Effect of the pH of the medium on the chemical shifts in the PMR spectra and on the distribution of the π-electron density

I. 3-Hydroxyquinoline derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The dependence of the chemical shift of the ring protons on the pH of the medium for a number of 3-hydroxyquinoline derivatives was studied by PMR spectroscopy. The regions of ionization of the molecules, which correspond to the ranges of acidic, neutral, and alkaline media, were found. In D2O, 3-hydroxyquinoline is present only in the uncharged hydroxy form. The presence of intramolecular hydrogen bonding in 4-dimethylaminomethyl-3-hydroxyquinoline has a substantial effect on the character of the dependence of the chemical shift on the pH of the medium; the existence of separate protonation of the nitrogen atoms of the ring and the side chain of 4-dimethylaminomethyl-3-hydroxyquinoline was established. The distribution of the π-electron density in the 3-hydroxyquinoline molecule is in good agreement with its chemical behavior during electrophilic substitution.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR. Scientific-Research Institute of Organic Intermediates and Dyes, Moscow

    V. P. Lezina, N. A. Andronova, L. D. Smirnov & K. M. Dyumaev

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  1. V. P. Lezina
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  2. N. A. Andronova
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  3. L. D. Smirnov
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  4. K. M. Dyumaev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1540–1545, November, 1971.

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Lezina, V.P., Andronova, N.A., Smirnov, L.D. et al. Effect of the pH of the medium on the chemical shifts in the PMR spectra and on the distribution of the π-electron density. Chem Heterocycl Compd 7, 1433–1437 (1971). https://doi.org/10.1007/BF00481113

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  • DOI: https://doi.org/10.1007/BF00481113

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