Russian Chemical Bulletin

, Volume 58, Issue 5, pp 920–925 | Cite as

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

  • A. A. Volod’kin
  • S. M. Lomakin
  • G. E. Zaikov
  • N. M. Evteeva
Full Articles


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.

Key words

N-acetylamino(3,5-di-tert-butyl-4-hydroxybenzyl)malonate hydrolysis decarboxylation antioxidants 


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  1. 1.
    H. J. Teuder, H. Rrause, V. Berariu, Lieb. Ann., 1978, 757.Google Scholar
  2. 2.
    C. W. Gear, Numerical Initial Value Problems in Ordinary Differential Equations, Prentice Hall, New York, 1971, 158.Google Scholar
  3. 3.
    N. B. Colthup, L. H. Daly, S. E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York-London, 1990, 319.Google Scholar
  4. 4.
    V. A. Russell, Lian Yu, J. Chem. Soc., Perkin Trans. 2, 2000, 913.Google Scholar
  5. 5.
    A. A. Volod’kin, R. D. Malysheva, V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 1594 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 182, 1633].Google Scholar
  6. 6.
    R. M. Guerra, I. Duran, P. Ortiz, Chemical Reaction: Quantitative Level of Liquid and Solid Phase, Nova Science Publishers, Inc., New York, 1992, pp. 59–74.Google Scholar
  7. 7.
    J. J. P. Stewart Computational, J. Mol. Mod., 2007, 13, 1173.CrossRefGoogle Scholar
  8. 8.
    D. V. Berdyshev, V. P. Glazunov, V. L. Novikov, Izv. Akad. Nauk, Ser. Khim., 2007, 400 [Russ. Chem. Bull., Int. Ed., 2007, 56, 413].Google Scholar
  9. 9.
    N. M. Emanuel, E. T. Denisov, Z. K. Maizus, Tsepnye reaktsii okisleniya uglevodorodov v zhidkoi faze [Chain Reactions of Hydrocarbon Oxidation in the Liquid Phase], Nauka, Moscow, 1965 (in Russian).Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • A. A. Volod’kin
    • 1
  • S. M. Lomakin
    • 1
  • G. E. Zaikov
    • 1
  • N. M. Evteeva
    • 1
  1. 1.N. M. Emanuel Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussian Federation

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