Formation of hydrotrioxides during ozonation of hydrocarbons on silica gel. Decomposition of hydrotrioxides

Elena V. Avzyanova, Qadir K. Timerghazin, Alexey F. Khalizov, Sergey L. Khursan, Leonid V. Spirikhin, Valery V. Shereshovets

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Hydrotrioxides (HT), ROOOH, from isopentane, 1,4-dimethylcyclohexane, 1,3-dimethylcyclohexane, decalin and triphenylmethane were synthesized for the first time by low-temperature ozonation of the corresponding hydrocarbons on a silica surface. Thermal decomposition of hydrotrioxides is accompanied by the formation of radicals and by infrared and visible chemiluminescence (CL). In solution the HTs form self-associates and react reversibly with the solvent (acetone) producing Bayer-Villiger type intermediates (unsymmetrical dialkyl trioxides). These reactions cause a complex character of the decomposition kinetics of HTs, as evidenced by monitoring the dependence of CL intensity on time. Activation parameters of thermal decomposition of HTs show a compensation effect (logA vs EA) which describes well the available experimental and theoretical data for the homolysis of organic trioxides.

Original languageEnglish (US)
Pages (from-to)87-96
Number of pages10
JournalJournal of Physical Organic Chemistry
Volume13
Issue number2
DOIs
StatePublished - Jan 1 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Association
  • Chemiluminescence
  • Free radicals
  • Hydrogen bonding
  • Hydrotrioxides
  • Mechanism
  • Ozone
  • Silica gel
  • Singlet oxygen

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