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Investigation in the Series of Substituted Butan- and Butenolides: XV. Transformations of 4-Hydroxy-2-butenolide in Water Media at Various pH Values

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Abstract

The 4-hydroxy-2-butenolide was established by polarographic method to undergo in water solutions fast tautomeric and acid-base transformations. Depending on pH of the medium the compound is present either as a cyclic irreducible form (at pH 0-4) or in the open-chain (carbonyl-containing) reducible forms (at pH > 4 and < 0). It is presumed that in going from the basic to strongly acidic medium and backwards occur consecutive equilibrium transitions of four species: cis-β-formylacrylic acid anion (A-), its neutral molecule (HA) existing as linear and cyclic tautomers, and protonated forms (H2A+ and H3A+). The formation mechanism thereof is considered.

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Authors and Affiliations

  1. Kuban State Technological University, Krasnodar, 350072, Russia

    N. K. Strizhov, V. V. Poskonin, L. A. Badovskaya & E. P. Kupina

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  1. N. K. Strizhov
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  2. V. V. Poskonin
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  3. L. A. Badovskaya
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  4. E. P. Kupina
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Strizhov, N.K., Poskonin, V.V., Badovskaya, L.A. et al. Investigation in the Series of Substituted Butan- and Butenolides: XV. Transformations of 4-Hydroxy-2-butenolide in Water Media at Various pH Values. Russian Journal of Organic Chemistry 38, 251–255 (2002). https://doi.org/10.1023/A:1015578003374

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