RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Reactivity of Inorganic α-Nucleophiles in Acyl Transfer in Aqueous and Micellar Media. IV. Peroxyhydrolysis of Acylcontaining Compounds in Organized Microheterogenic Systems

PII
S30346304S0514749225040135-1
DOI
10.7868/S3034630425040135
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 4
Pages
466-474
Abstract
Micellar effects in perhydrolysis and base catalyzed hydrolysis of 4-nitrophenyl esters of phosphoric, phosphonic and toluolsulphonic acids in organized microheterogeneous systems based on dicationic (Gemini surfactant, GS – AlkIm–(CH)-ImAlk-2Br, Alk = CH or CH) and monocationic (AlkImCH Br, Alk = CH or CH) surfactants have been analyzed. The effect of concentration of reagents is the main factor responsible for micellar catalysis. Hydroperoxide α-effect described as second order rate constants ratio for perhydrolysis and base catalyzed hydrolysis remains in organized media, and, depending on surfactant/substrate nature, may amount to ~100.
Keywords
экотоксиканты димерные катионные ПАВ пероксигидролиз эффект концентрирования α-эффект
Date of publication
15.12.2025
Year of publication
2025
Number of purchasers
0
Views
25

References

  1. 1. Белоусова И.А., Зубарева Т.М., Гайдаш Т.С., Разумова Н.Г., Туровская М.К., Панченко Б.В., Прокопьева Т.М., Михайлов В.А. ЖОрХ. 2021, 57, 352–362. @@Belousova I.A., Zubareva T.M., Gaidash T.S., Razumova N.G.,Turovskaya M.K., Panchenko B.V., Prokop’eva T.M., Mikhailov V.A. Russ. J. Org. Chem. 2021, 57, 338–346. doi 10.31857/S0514749221030034
  2. 2. Samiey B., Cheng C.-H., Wu J. J. Chem., 2014, 1–4. doi 10.1155/2014/908476
  3. 3. Bedford C.T. Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives. In: Organic Reaction Mechanisms 2014, Ed. A.C. Knipe, Wiley, 2018, 87–122. doi 10.1002/9781118941829.ch2
  4. 4. Kim K., Tsay O.G., Atwood D.A., Churchill D.G. Chem. Rev. 2011, 111, 5345–5403. doi 10.1021/cr100193y
  5. 5. Duirk S.E., Desetto L.M., Davis G.M. Environ. Sci. Technol. 2009, 43, 2335–2340. doi 10.1021/es802868y
  6. 6. Deraedt C., Didier A. Coord. Chem. Rev. 2016, 324, 106–122. doi 10.1016/j.ccr.2016.07.007
  7. 7. Pavez P., Oliva G., Millán D. ACS Sustain. Chem. Eng. 2016, 4, 7023–7031. doi 10.1021/acssuschemeng.6b01923
  8. 8. Симаненко Ю.С., Попов А.Ф., Прокопьева Т.М., Карпичев Е.А., Савелова В.А., Супрун И.П., Бантон К.А. ЖОрХ. 2002, 38, 1341–1353. @@ @@Simanenko Yu.S., Popov A.F., Prokop'eva T.M., Karpichev E.A., Savelova V.A., Suprun I.P., Bunton C.A. Russ. J. Org. Chem. 2002, 38, 1286–1298. doi 10.1023/A:1021699628721
  9. 9. Wagner G.W., Sorrick D.C., Procell L.R., Brickhouse M.D., Mcvey I.F., Schwartz L.I. Langmuir. 2007, 23, 1178–1186. doi 10.1021/la062708i
  10. 10. Yang Yu-Chu. Acc. Chem. Res.1999, 32, 109–115. doi 10.1021/ar970154s
  11. 11. Talmage S.S., Watson A.P., Hauschild V., Munro N.B., King J. Curr. Org. Chem. 2007, 11, 285–298. doi 10.2174/138527207779940892
  12. 12. Cassagne T., Cristau H.-J., Delmas G., Desgranges M., Lion C., Magnaud G., Torreilles É., Virieux D. Heteroat. Chem. 2001, 12, 485–490. doi 10.1002/hc.1074
  13. 13. Wagner G.W., Yang Yu-Chu. Ind. Eng. Chem. Res. 2002, 41, 1925–1928. doi 10.1021/ie010732f
  14. 14. Yao H., Richardson D.E. J. Am. Chem. Soc. 2003, 125, 6211–6221. doi 10.1021/ja0274756
  15. 15. Bunton C.A., Gillitt N.D. J. Phys. Org. Chem. 2002, 15, 29–35. doi 10.1002/poc.442
  16. 16. Зубарева Т.М., Аникеев А.В., Карпичев Е.А., Редько А.Н., Прокопьева Т.М., Попов А.Ф. Теорет. эксперим.хим., 2011, 47, 363–369. @@Zubareva T.M., Anikeev A.V., Karpichev E.A., Red'ko A.N., Prokop'eva T.M., Popov A.F. Theor. Exp. Chem. 2011, 47, 377–383. doi 10.1007/s11237-012-9230-5
  17. 17. Pisárčik M., Polakovičová M., Markuliak M., Lukáč M., Devínsky F. Molecules. 2019, 24, 1–13. doi 10.3390/molecules24081481
  18. 18. Zana R. Adv. Coll. Interface Sci. 2002, 97, 205–253. doi 10.1016/s0001-8686(01)00069-0
  19. 19. Капитанов И.В., Прокопьева Т.М., Садовский Ю.С., Соломойченко Т.Н., Туровская М.К., Пискунова Ж.П., Разумова Н.Г., Попов А.Ф. Укр. хим. ж. 2014, 80, 30–37.
  20. 20. Berezin I.V., Martinek K., Yatsimirskii A.K. Russ. Chem. Rev. 1973, 42, 787–802. doi 10.1070/rc1973v042n10abeh002744
  21. 21. Bunton C.A. Adv. Coll. Interface Sci. 2006, 123–126, 333–343. doi 10.1016/j.cis.2006.05.008
  22. 22. Bhattacharya S., Kumar V.P. J. Org. Chem. 2004, 69, 559–562. doi 10.1021/jo034745+
  23. 23. Wetting S.D., Verrall R.E. J. Coll. Interface Sci. 2001, 235, 310–316. doi 10.1006/jcis.2000.7348
  24. 24. Wetting S.D., Novak P., Verrall R.E. Langmuir. 2002, 18, 5354–5359. doi 10.1021/la011782s
  25. 25. Прокопьева Т.М., Белоусова И.А., Туровская М.К., Разумова Н.Г., Панченко Б.В., Михайлов В.А. ЖОрХ. 2018, 54, 1621–1628. @@Prokop’eva T.M., Belousova I.A., Turovskaya M.K., Razumova N.G., Panchenko B.V., Mikhailov V.A. Russ. J. Org. Chem. 2018, 54, 1630–1637. doi 10.1134/S1070428018110027
  26. 26. Капитанов И.В., Белоусова И.А., Шумейко А.Е., Кострикин М.Л., Прокопьева Т.М., Попов А.Ф. ЖОрХ, 2014, 50, 706–715. @@Kapitanov I.V., Belousova I.A., Shumeiko A.E., Kostrikin M.L., Prokop’eva T.M., Popov A.F. Russ. J. Org. Chem. 2014, 50, 694–704. doi 10.1134/S1070428014050133
  27. 27. Prokop’eva T.M., Mirgorodskaya A.B., Belousova I.A., Zubareva T.M., Turovskaya M.K., Panchenko B.V., Razumova N.G., Gaidash T.S., Mikhailov V.A. Chem. Safety Sci. 2021, 5, 8–48. doi 10.25514/CHS.2021.2.20001
  28. 28. Зубарева Т.М., Белоусова И.А., Прокопьева Т.М., Гайдаш Т.С., Разумова Н.Г., Панченко Б.В., МихайловВ.А. ЖОрХ, 2020, 56, 70–77. @@Zubareva T.M., Belousova I.A., Prokop’eva T.M., Gaidash T.S., Razumova N.G., Panchenko B.V., Mikhailov V.A. Russ. J. Org. Chem. 2020, 56, 53–58. doi 10.1134/S1070428020010091
  29. 29. Pang Q.-H., Zang R.-R., Kang G.-L., Li J.-M., Hu W., Meng X.-G., Zeng X.-C. J. Dispers. Sci. Technol. 2006, 27, 671–675. doi 10.1080/01932690600660541
  30. 30. Leclercq L., Douyère G., Nardello-Rataj V. Catalysts. 2019, 9, 163. doi 10.3390/catal9020163
  31. 31. DePuy C. H., Della E. W., Filley J., Grabowski J. J., Bierbaum V. M. J. Am. Chem. Soc. 1983, 105, 2481–2482.  doi 10.1021/ja00346a066 
  32. 32. Voloshina A.D., Gumerova S.K., Sapunova А.S., Kulik N.V., Mirgorodskaya A.B., Kotenko A.A., Prokopyeva T.M., Mikhailov V.A., Zakharova L.Ya, Sinyashin O.G. Biochim. Biophys. Acta, Gen. Subjs. 2020, 1864, 129728. doi 10.1016/j.bbagen.2020.129728
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