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Alkaline hydrolysis of diethyl N-acetylamino(3,5-di-tert-butyl-4-hydroxybenzyl)malonate

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Abstract

Alkaline hydrolysis of diethyl N-acetylamino(3,5-di-tert-butyl-4-hydroxybenzyl)malonate is accompanied by decarboxylation. The efficiency of this process depends on the temperature and ratio of the reactants. A possibility of tautomerism with migration of the proton of phenolic hydroxyl and the influence of the structure on the antioxidation properties were considered on the basis of analysis of the IR spectral data and quantum chemical (PM6) calculation of the structures. The energies of homolysis of the O-H bond of phenolic hydroxyl were calculated for a series of the synthesized compounds. It is proposed to predict the antioxidation activity on the basis of these values.

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Authors and Affiliations

  1. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    A. A. Volod’kin, S. M. Lomakin, G. E. Zaikov & N. M. Evteeva

Authors
  1. A. A. Volod’kin
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  2. S. M. Lomakin
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  3. G. E. Zaikov
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  4. N. M. Evteeva
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Corresponding author

Correspondence to A. A. Volod’kin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 900–905, May, 2009.

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Volod’kin, A.A., Lomakin, S.M., Zaikov, G.E. et al. Alkaline hydrolysis of diethyl N-acetylamino(3,5-di-tert-butyl-4-hydroxybenzyl)malonate. Russ Chem Bull 58, 920–925 (2009). https://doi.org/10.1007/s11172-009-0115-2

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  • DOI: https://doi.org/10.1007/s11172-009-0115-2

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