Kinetics of the diels-alder reaction of 2,5-dimethylfuran with N-phenylmaleimide: high hydrostatic pressure, temperature, and solvent effects

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Abstract

The rate constants of the Diels-Alder reaction of 2,5-dimethylfuran (1) with N -phenylmaleimide (2) in 5 solvents in the range of temperature 25-45°C and pressure 1-1000 bar have been determined. Activation enthalpy, entropy, Gibbs free energy and volume parameters have been calculated. The equilibrium constants of the 1 + 2 reaction in benzene in the temperature range 25-55°C have been determined, and the reaction enthalpy and entropy have been calculated.

About the authors

D. A. Kornilov

Ufa University of Science and Technology;Kazan Federal University, A.M. Butlerov Institute of Chemistry

Email: dima_himik2@mail.ru

References

  1. Brydson J.A. Plastics Materials. London: Elsevier, 1999, 7th Edn.
  2. Kainulainen T.P., Erkkilä P., Hukka T.I., Sirviö J.A., Heiskanen J.P. ACS Appl. Polym. Mater. 2020, 2, 3215-3225. doi: 10.1021/acsapm.0c00367
  3. Ma Y., Du Y., Zhao J., Yuan X., Hou X. Polymers. 2020. 12, 1480. doi: 10.3390/polym12071480
  4. Wang Z., Cao N., He J., Du R., Liu Y., Zhao G. J. Appl. Polym. Sci. 2017, 134, 44799. doi: 10.1002/app.44799
  5. Briou B., Ameduri B., Boutevin B. Chem. Soc. Rev. 2021, 50, 11055-11097. doi: 10.1039/D0CS01382J
  6. Dong Q.-M., Dong S., Shen C., Cao Q.-H., Song M.-Y., He Q.-R., Wang X.-L., Yang X.-J., Tang J.-J., Gao J.-M. Sci. Rep. 2018, 8, 8372. doi: 10.1038/s41598-018-26747-0
  7. Alizadeh M., Jalal M., Hamed K., Saber A., Kheirouri S., Tabrizi F.P.F., Kamari N. J. Inflamm. Res. 2020, 2020, 451-463. doi: 10.2147/JIR.S262132
  8. Cui Z., Li Y., Ling Y., Huang J., Cui J., Wang R., Yang X. Eur. J. Med. Chem. 2010, 45, 5576-5584. doi: 10.1016/j.ejmech.2010.09.007
  9. Koca M., Servi S., Kirilmis C., Ahmedzade M., Kazaz C., Özbek B., Ötük G. Eur. J. Med. Chem. 2005, 40, 1351-1358. doi: 10.1016/j.ejmech.2005.07.004
  10. Kirilmis C., Ahmedzade M., Servi S., Koca M., Kizirgil A., Kazaz C. Eur. J. Med. Chem. 2008, 43, 300-308. doi: 10.1016/j.ejmech.2007.03.023
  11. Kirsch G., Abdelwahab A.B., Chaimbault P. Molecules. 2016, 21, 1322. doi: 10.3390/molecules21101322
  12. Chand K., Rajeshwari, Hiremathad A., Singh M., Santos M.A., Keri R.S. Pharmacol. Rep. 2017, 69, 281-295. doi: 10.1016/j.pharep.2016.11.007
  13. Li B., Ahmed F., Bernstein P.S. Arch. Biochem. Biophys. 2010, 504, 56-60. doi: 10.1016/j.abb.2010.07.024
  14. Hoang A.T., Nižetić S., Ölçer A.I. Fuel. 2021, 285, 119140. doi: 10.1016/j.fuel.2020.119140
  15. Fringuelli F., Taticchi A. Dienes in the Diels-Alder Reaction. New York: Wiley, 1990.
  16. Li Z., Jiang Y., Li Y., Zhang H., Li H., Yang S. Catal. Sci. Technol. 2022, 12, 1902-1921. doi: 10.1039/D1CY02122B
  17. Pehere A.D., Xu S., Thompson S.K., Hillmyer M.A., Hoye T.R. Org. Lett. 2016, 18, 2584-2587. doi: 10.1021/acs.orglett.6b00929
  18. Salavati-fard T., Caratzoulas S., Lobo R.F., Doren D.J. ACS Catal. 2017, 7, 2240-2246. doi: 10.1021/acscatal.6b02682
  19. Galkin K.I., Sandulenko I.V., Polezhaev A.V. Processes. 2022, 10, 30. doi: 10.3390/pr10010030
  20. Gil M.V., Luque-Agudo V., Roman E., Serrano J.A. Synlett. 2014, 25, 2179-2183. doi: 10.1055/s-0034-1378560
  21. Киселев В.Д., Корнилов Д.А., Аникин О.В., Племенков В.В., Коновалов А.И. ЖОрХ. 2018, 54, 1073-1077.
  22. Kiselev V.D., Kornilov D.A., Anikin O.V., Plemenkov V.V., Konovalov A.I. Russ. J. Org. Chem. 2018, 54, 1080-1084. doi: 10.1134/S1070428018070187
  23. Kiselev V.D., Kornilov D.A., Anikin O.V., Shulyatiev A.A., Kolesnikova A.O., Konovalov A.I. Int. J. Chem. Kinet. 2018, 50, 651-658. doi: 10.1002/kin.21189
  24. Киселев В.Д., Корнилов Д.А., Аникин О.В., Седов И.А., Коновалов А.И. ЖОрХ. 2017, 53, 1828-1833.
  25. Kiselev V.D., Kornilov D.A., Anikin O.V., Sedov I.A., Konovalov A.I. Russ. J. Org. Chem. 2017, 53, 1864-1869. doi: 10.1134/S1070428017120144
  26. Kiselev V.D., Kornilov D.A., Konovalov A.I. Int. J. Chem. Kinet. 2017, 49, 562-575. doi: 10.1002/kin.21094
  27. Kiselev V.D., Kornilov D.A., Lekomtseva I.I, Konovalov A.I. Int. J. Chem. Kinet. 2015, 47, 289-301. doi: 10.1002/kin.20908
  28. Kiselev V.D., Konovalov A.I. J. Phys. Org. Chem. 2009, 22, 466-483. doi: 10.1002/poc.1503
  29. Kiselev V.D., Kornilov D.A., Sedov I.A., Konovalov A.I. Int. J. Chem. Kinet. 2017, 49, 61-68. doi: 10.1002/kin.21057
  30. Киселев В.Д., Корнилов Д.А., Аникин О.В., Латыпова Л.И., Коновалов А.И. ЖФХ. 2017, 91, 446-449.
  31. Kiselev V.D., Kornilov D.A., Anikin O.V., Latypova L.I., Konovalov A.I. Russ. J. Phys. Chem. A. 2017, 91, 464-467. doi: 10.1134/S0036024417030128
  32. Veszpremi T., Nyulaszi L., Nagy J. J. Organomet. Chem. 1987, 331, 175-180. doi: 10.1016/0022-328X(87)80019-0
  33. Derrick P.J., Åsbrink L., Edqvist O., Jonsson B.-Ö., Lindholm E. Int. J. Mass Spectrom. Ion Phys. 1971, 6, 161-175. doi: 10.1016/0020-7381(71)80001-3
  34. Корнилов Д.А., Киселев В.Д., Аникин О.В., Колесникова А.О., Шулятьев А.А. ЖОрХ. 2019, 55, 17-21.
  35. Kornilov D.A., Kiselev V.D., Anikin O.V., Kolesnikova A.O., Shulyatiev A.A. Russ. J. Org. Chem. 2019, 55, 7-10. doi: 10.1134/S1070428019010020
  36. Cooley J.H., Williams R.V. J. Chem. Educ. 1997, 74, 582-585. doi: 10.1021/ed074p582
  37. Hepler L.G. J. Phys. Chem. 1965, 69, 965-967. doi: 10.1021/j100887a046
  38. Kornilov D.A., Kiselev V.D. J. Chem. Eng. Data. 2015, 60, 3571-3580. doi: 10.1021/acs.jced.5b00514
  39. Riddick J.A., Bunger W.B., Sakano T.K. Organic Solvents: Physical Properties and Methods of Purification. New York: Wiley, 1986, 4th Edn.
  40. Kornilov D.A., Kiselev V.D. Int. J. Chem. Kinet. 2015, 47, 389-394. doi: 10.1002/kin.20916
  41. Kiselev V.D., Bolotov A.V., Satonin A.P., Shakirova I.I., Kashaeva H.A., Konovalov A.I. J. Phys. Chem. B. 2008, 112, 6674-6682. doi: 10.1021/jp800513d

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