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Acid properties of the 2,2,6,6-tetramethyl-1-oxopiperidinium cation and 2,2,6,6-tetramethyl-1-hydroxypiperidine 1-oxide

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    In aqueous solutions of 2,2,6,6-tetramethyl-1-oxopiperidinium salts and salts of 1-hydroxypiperidine 1-oxide, the oxopiperidinium cation

    is in equilibrium with 1-hydroxypiperidine 1-oxide

    , and the piperidine 1,1-dioxide anion,

    . At [OH−] > 2 mole/liter, this equilibrium is shifted by more than 95% to the

    side, and at pH < 12 shifted to more than 98% to the

    side.

  2. 2.

    2,2,6,6-Tetramethyl-1-hydroxypiperidine 1-oxide is amphoteric; it is a weak protic acid and a strong base for the conjugated

    acid.

  3. 3.

    It is possible that the oxoimmonium cations,

    , are intermediates for the synthesis of carbonyl compounds from nitronic acids and nitroalkanes (Nef reaction).

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Authors and Affiliations

  1. Branch of the Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka

    V. D. Sen', V. A. Golubev & T. M. Kosheleva

Authors
  1. V. D. Sen'
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  2. V. A. Golubev
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  3. T. M. Kosheleva
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2001–2004, September, 1979.

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Sen', V.D., Golubev, V.A. & Kosheleva, T.M. Acid properties of the 2,2,6,6-tetramethyl-1-oxopiperidinium cation and 2,2,6,6-tetramethyl-1-hydroxypiperidine 1-oxide. Russ Chem Bull 28, 1847–1850 (1979). https://doi.org/10.1007/BF00952461

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  • DOI: https://doi.org/10.1007/BF00952461

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