Features of the initial stage of oxidation of N-hydroxyphthalimide by potassium permanganate

TitleFeatures of the initial stage of oxidation of N-hydroxyphthalimide by potassium permanganate
Publication TypeJournal Article
Year of Publication2016
AuthorsOpeyda, LI, Popov, AF
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2016.04.086
Issue4
SectionChemistry
Pagination86-91
Date Published4/2016
LanguageUkrainian
Abstract

The kinetics of oxidation of N-hydroxyphthalimide by potassium permanganate in acetone and its mixtures with water is studied. The accelerating effect of water on the kinetics of the initial stage of the process has been shown. Using the method of quantum chemistry, the reactivity of particles participating in the reaction of H-atom abstraction from the NO−H bond and the influence of protonation and hydratation was evaluated that gives possibility to explain the basic kinetic patterns obtained experimentally.
Keywordshydratation, N-hydroxyphthalimide, phthalimide-N-oxyl radical, potassium permanganate, protonation, quantum-chemical method
References: 
  1. Iwahama T., Syojyo K., Sakaguchi S., Ishii Y. Org. Proc. Res. Dev., 1998, 2, No 4: 255–260. https://doi.org/10.1021/op980016y
  2. Jiang J., Jing Y., Zhang Y. et al. Catal. Lett., 2011, 141, Iss. 4: 544–548. https://doi.org/10.1007/s10562-010-0507-9
  3. Li X., Xu J., Wang F. et al. Catal. Lett., 2006, 108, Iss. 3: 137–140. https://doi.org/10.1007/s10562-006-0034-x
  4. Ishii Y., Sakaguchi S. Catal. Today, 2006, 117, No 1: 105–113. https://doi.org/10.1016/j.cattod.2006.05.006
  5. Feng J.-B., Wu X.-F. Appl. Organometal. Chem., 2015, 29, Iss. 2: 63–86. https://doi.org/10.1002/aoc.3244
  6. Opeida L. I., Mavienko A. G., Siminiv M. A. Nauk. Pratsi DonNTU. Ser. Khimia i khimichna tekhnolohia, 2014, Iss. 2: 104–110 (in Russian).
  7. Gardner K. A., Kuehnert L. L., Mayer J. M. Inorg. Chem, 1997, 36, No 10: 2069–2078. https://doi.org/10.1021/ic961297y
  8. Gardner K. A., Mayer J. M. Science, 1995, 269: 1849–1851. https://doi.org/10.1126/science.7569922
  9. Rudakov E. S., Lobachev V. L. Russ. Chem. Bull., 2000, 49, No 5: 761–777. https://doi.org/10.1007/BF02494695
  10. Stewart J. J. P. J. Mol. Model., 2007, 13: 1173–1213. https://doi.org/10.1007/s00894-007-0233-4
  11. Gardner K. A., Mayer J. M. Science, 1995, 269: 1849–1851. https://doi.org/10.1126/science.7569922
  12. Koshino N., Cai Y., Espenson J. H. J. Phys. Chem., 2003, 107: 4262–4267. https://doi.org/10.1021/jp0276193