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Russian Chemical Bulletin

, Volume 57, Issue 7, pp 1492–1495 | Cite as

Protonation of 1,3- and 1,4-dinitrobenzene dianions

  • A. S. Mendkovich
  • M. A. Syroeshkin
  • L. V. Mikhalchenko
  • A. I. Rusakov
  • V. P. Gultyai
Full Articles

Abstract

The protonation of the electrochemically generated (0.1 M solution of tetrabutylammonium perchlorate in DMF) 1,3-dinitrobenzene (1) dianions with phenol, ethanol, tert-butanol, and 1-butyl-3-methylimidazolium cation was studied by cyclic voltammetry and chronoamperometry at the carbositall working electrode. The rate constants for the protonation (k) of the dianion of compound 1 by phenol, 1-butyl-3-methylimidazolium cation, ethanol, and tert-butanol were estimated by the comparison of the data of cyclic voltammetry and chronoamperometry with the digital simulation results, being 100, 50, 1.5, and 0.01 L mol−1 s−1, respectively. The similarly obtained k value for the protonation of the dianion of 1,4-dinitrobenzene (2) with phenol is 13 L mol−1 s−1. According to the quantum chemical calculation results, the protonation of the dianions of compounds 1 and 2 with phenol and 1-butyl-3-methylimidazolium cation can be classified as orbital-controlled reactions.

Key words

electrochemical reduction 1,3-dinitrobenzene 1,4-dinitrobenzene protonation phenol 1-butyl-3-methylimidazolium tetrafluoroborate 

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Copyright information

© Springer Science+Business Media, Inc.  2008

Authors and Affiliations

  • A. S. Mendkovich
    • 1
  • M. A. Syroeshkin
    • 1
  • L. V. Mikhalchenko
    • 1
  • A. I. Rusakov
    • 2
  • V. P. Gultyai
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.P. G. Demidov Yaroslavl State UniversityYaroslavlRussian Federation

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