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Polarographic investigation of the tautomeric transformations of β-formylacrylic acid and of the hydrolysis of its ethyl pseudoester. I

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Abstract

A polarographic method was used to study the cis (HAc), trans (HAt), and lactol (L) forms of formylacrylic acid (FAA) and its ethyl pseudoester (E) and their interconversions. It is shown that the slow step in the process E⇌L⇌HAc⇌Ac − is hydrolysis of E. The pH of the solution has a substantial effect on the state of the equilibrium in all of the steps because of the shift in the equilibrium HAc⇌Ac −. The equilibrium constants of all of the steps and the rate constant of the hydrolysis of E as a function of the pH of the solution were found. The most stable of the three forms of FAA is HAt. The cis form exists only in solutions. The polarographic reduction of HAc and HAt at the ethylene bond proceeds at more positive potentials than the reduction of maleic and fumaric acids. In contrast to HAc, HAt does not form a polarographic dissociation curve; this is explained by the closeness of the potentials for the reduction of HAt and At −.

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Authors and Affiliations

  1. Krasnodar Polytechnical Institute, USSR

    I. A. Kuzovnikova, L. A. Badovskaya, Ya. I. Tur'yan & V. G. Kul'nevich

Authors
  1. I. A. Kuzovnikova
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  2. L. A. Badovskaya
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  3. Ya. I. Tur'yan
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  4. V. G. Kul'nevich
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 737–742, June, 1974.

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Kuzovnikova, I.A., Badovskaya, L.A., Tur'yan, Y.I. et al. Polarographic investigation of the tautomeric transformations of β-formylacrylic acid and of the hydrolysis of its ethyl pseudoester. I. Chem Heterocycl Compd 10, 640–644 (1974). https://doi.org/10.1007/BF00480912

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  • DOI: https://doi.org/10.1007/BF00480912

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