Везде

RAS Chemistry & Material ScienceХимическая физика Advances in Chemical Physics

  • ISSN (Print) 0207-401X
  • ISSN (Online) 3034-6126

Reaction of atomic fluorine with benzene

You can
PII
10.31857/S0207401X24060018-1
DOI
10.31857/S0207401X24060018
Publication type
Article
Status
Published
Authors
S. O. Adamson
  • Affiliation: Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences
Volume/ Edition
Volume 43 / Issue number 6
Pages
3-15
Abstract
Benzene is one of the most common classes of chemicals in industry. As a rule, it enters the atmosphere as a result of man-made accidents, during the evaporation of solvents, etc. Benzene and its derivatives are toxic and have a negative impact on the environment and the human body. Therefore, issues of benzene transformation in the atmosphere are of increased interest. In present work, the structures and electronic energies of equilibrium configurations and transition complexes of the C₆H₆ F and C₆H₆F⁺ systems are calculated using the density functional theory. It has been shown that the interaction of benzene with atomic fluorine can proceed through two channels, i.e. the elimination of hydrogen with the formation of a phenyl radical and the addition of a fluorine atom with the formation of an ipso-fluorocyclohexadienyl radical. It has been established that for the dissociation of ipso-fluorocyclohexadienyl radical into fluorobenzene and atomic hydrogen, it is necessary to expend about 27 kcal/mol. This indicates a low probability of this process occurring at low temperatures. Under experimental conditions, when the temperature of fluorine atoms is about 1000 K, the ipso-fluorocyclohexadienyl radical decomposes to form fluorobenzene. In this case, the occurrence of secondary reactions is unlikely. The conclusions drawn from the analysis of the results of quantum chemical calculations are in good agreement with the experimental data.
Keywords
газофазная реакция механизм реакции гамильтониан реакционного пути бензол атомарный фтор теория функционала плотности
Date of publication
14.09.2025
Year of publication
2025
Number of purchasers
0
Views
4

References

  1. 1. Cochran E.L., Adrian F.J., Bowers V.A. // J. Phys. Chem. 1970. V. 74. № 10. P. 2083; https://doi.org/10.1021/j100909a006
  2. 2. Ebrecht J., Hack W., Wagner H.G. // Ber. Bunseng. Phys. Chem. 1989. V. 93. № 5. P. 619; https://doi.org/10.1002/bbpc.19890930520
  3. 3. Vasek A.H., Sams L.C. // J. Fluor. Chem. 1974. V. 3. № 3–4. P. 397; https://doi.org/10.1016/S0022-1139 (00)82640-8
  4. 4. Parson J.M., Lee Y.T. // J. Chem. Phys. 1972. V. 56. № 9. P. 4658; https://doi.org/10.1063/1.1677917
  5. 5. Parson J.M., Shobatake K., Lee Y.T. et al. // J. Chem. Phys. 1973. V. 59. № 3. P. 1402; https://doi.org/10.1063/1.1680198
  6. 6. Parson J.M., Shobatake K., Lee Y.T. et al. // Faraday Discuss. Chem. Soc. 1973. V. 55. P. 344; https://doi.org/10.1039/dc9735500344
  7. 7. Shobatake K., Parson J.M., Lee Y.T. et al. // J. Chem. Phys. 1973. V. 59. № 3. P. 1427; https://doi.org/10.1063/1.1680200
  8. 8. Shobatake K., Lee Y.T., Rice S.A. // J. Chem. Phys. 1973. V. 59. № 3. P. 1435; https://doi.org/10.1063/1.1680201
  9. 9. Grover J.R., Wen Y., Lee Y.T. et al. // J. Chem. Phys. 1988. V. 89. № 2. P. 938; https://doi.org/10.1063/1.455162
  10. 10. Jacox M.E. // J. Phys. Chem. 1982. V. 86. № 5. P. 670; https://doi.org/10.1021/j100394a016
  11. 11. Cramer J.A., Rowland F.S. // J. Amer. Chem. Soc. 1974. V. 96. № 21. P. 6579; https://doi.org/10.1021/ja00828a006
  12. 12. Moehlmann J.G., Gleaves J.T., Hudgens J.W. et al. // J. Chem. Phys. 1974. V. 60. № 12. P. 4790; https://doi.org/10.1063/1.1680982
  13. 13. Moehlmann J.G., McDonald J.D. // J. Chem. Phys. 1975. V. 62. № 8. P. 3061; https://doi.org/10.1063/1.430904
  14. 14. Obara M., Fujioka T. // Jpn. J. Appl. Phys. 1975. V. 14. № 8. P. 1183; https://doi.org/10.1143/JJAP.14.1183
  15. 15. Васильев Е.С., Волков Н.Д., Карпов Г.В. и др. // ЖФХ. 2020. Т. 94. № 10. С. 1484; https://doi.org/10.31857/S0044453720100295
  16. 16. Васильев Е.С., Волков Н.Д., Карпов Г.В. и др. // Хим. физика. 2021. Т. 40. № 10. С. 30; https://doi.org/10.31857/S0207401X21100125
  17. 17. Smith D.J., Setser D.W., Kim K.C. et al. // J. Phys. Chem. 1977. V. 81. № 9. P. 898; https://doi.org/10.1021/j100524a019
  18. 18. Mason R.S., Parry A.J., Milton D.M.P. // J. Chem. Soc. Faraday Trans. 1994. V. 90. № 10. P. 1373; https://doi.org/10.1039/ft9949001373
  19. 19. Tsao M.L., Hadad C.M., Platz M.S. // J. Amer. Chem. Soc. 2003. V. 125. № 27. P. 8390; https://doi.org/10.1021/ja035095u
  20. 20. Zhao Y., Truhlar D.G. // Acc. Chem. Res. 2008. V. 41. № 2. P. 157; https://doi.org/10.1021/ar700111a
  21. 21. Zhao Y., Truhlar D.G. // J. Chem. Theor. Comp. 2008. V. 4. № 11. P. 1849; https://doi.org/10.1021/ct800246v
  22. 22. Адамсон С.О. // Хим. физика. 2016. Т. 35. № 1. С. 76; https://doi.org/10.7868/S0207401X16010027
  23. 23. Hehre W.J., Ditchfield R., Pople J.A. // J. Chem. Phys. 1972. V. 56. № 5. P. 2257; https://doi.org/10.1063/1.1677527
  24. 24. Hariharan P.C., Pople J.A. // Theor. Chim. Acta. 1973. V. 28. № 3. P. 213; https://doi.org/10.1007/BF00533485
  25. 25. Clark T., Chandrasekhar J., Spitznagel G.W. et al. // J. Comput. Chem. 1983. V. 4. № 3. P. 294; https://doi.org/10.1002/jcc.540040303
  26. 26. Dunning T.H. // J. Chem. Phys. 1989. V. 90. № 2. P. 1007; https://doi.org/10.1063/1.456153
  27. 27. Kendall R.A., Dunning T.H., Harrison R.J. // J. Chem. Phys. 1992. V. 96. № 9. P. 6796; https://doi.org/10.1063/1.462569
  28. 28. Schmidt M.W., Baldridge K.K., Boatz J.A. et al. // J. Comp. Chem. 1993. V. 14. № 11. P. 1347; https://doi.org/10.1002/jcc.540141112
  29. 29. Gordon M.S., Schmidt M.W. // Theory and Applications of Computational Chemistry. Amsterdam: Elsevier, 2005. P. 1167; https://doi.org/10.1016/B978-044451719-7/50084-6
  30. 30. Huber K.P., Herzberg G. // In: Molecular Spectra and Molecular Structure. Boston: Springer, 1979. P. 8; https://doi.org/10.1007/978-1-4757-0961-2_2
  31. 31. Feller D., Peterson K.A. // J. Mol. Struct. THEOCHEM. 1997. V. 400. № 1–3. P. 69; https://doi.org/10.1016/S0166-1280 (97)90269-4
  32. 32. Gondal M.A., Rohrbeck W., Urban W. et al. // J. Mol. Spectrosc. 1983. V. 100. № 2. P. 290; https://doi.org/10.1016/0022-2852 (83)90087-5
  33. 33. Darwent B. Bond dissociation energies in simple molecules. Gaithersburg: National Bureau of Standards, 1970; https://doi.org/10.6028/NBS.NSRDS.31
  34. 34. Porter T.L., Mann D.E., Acquista N. // J. Mol. Spectrosc. 1965. V. 16. № 2. P. 228; https://doi.org/10.1016/0022-2852 (65)90121-9
  35. 35. Hildenbrand D.L. // Chem. Phys. Lett. 1975. V. 32. № 3. P. 523; https://doi.org/10.1016/0009-2614 (75)85231-6
  36. 36. Colbourn E.A., Dagenais M., Douglas A.E. et al. // Can. J. Phys. 1976. V. 54. № 13. P. 1343; https://doi.org/10.1139/p76-159
  37. 37. Burgess D.R., Manion J.A. // J. Phys. Chem. Ref. Data. 2021. V. 50. № 2. 023102; https://doi.org/10.1063/5.0028874
  38. 38. Espinosa-García J., Bravo J.L., Rangel C. // J. Phys. Chem. A. 2007. V. 111. № 14. P. 2761; https://doi.org/10.1021/jp0688759
  39. 39. Foon R., Reid G.P. // Trans. Faraday Soc. 1971. V. 67. P. 3513; https://doi.org/10.1039/tf9716703513
  40. 40. Persky A. // Chem. Phys. Lett. 1998. V. 298. № 4–6. P. 390; https://doi.org/10.1016/S0009-2614 (98)01154-3
  41. 41. Atkinson R., Baulch D.L., Cox R.A. et al. // J. Phys. Chem. Ref. Data. 1997. V. 26. № 3. P. 521; https://doi.org/10.1063/1.556011
  42. 42. Hrusak J., Schroeder D., Weiske T. et al. // J. Amer. Chem. Soc. 1993. V. 115. № 5. P. 2015; https://doi.org/10.1021/ja00058a057
  43. 43. Solcà N., Dopfer O. // J. Amer. Chem. Soc. 2003. V. 125. № 5. P. 1421; https://doi.org/10.1021/ja021036p
  44. 44. Dopfer O., Solcà N., Lemaire J. et al. // J. Phys. Chem. A. 2005. V. 109. № 35. P. 7881; https://doi.org/10.1021/jp052907v
  45. 45. Dopfer O. // J. Phys. Org. Chem. 2006. V. 19. № 8–9. P. 540; https://doi.org/10.1002/poc.1053
  46. 46. Adamson S.O., Kharlampidi D.D., Shtyrkova A.S. et al. // Atoms. 2023. V. 11. № 10. 132; https://doi.org/10.3390/atoms11100132
  47. 47. Васильев Е.С., Карпов Г.В., Шартава Д.К. и др. // Хим. физика. 2022. Т. 41. № 5. С. 10; https://doi.org/10.31857/S0207401X22050119
  48. 48. Морозов И.И., Васильев Е.С., Бутковская Н.И. и др. // Хим. физика. 2023. Т. 42. № 10. С. 26; https://doi.org/10.31857/S0207401X23100114
  49. 49. Морозов И.И., Васильев Е.С., Волков Н.Д. и др. // Хим. физика. 2022. Т. 41, № 10. С. 16; https://doi.org/10.31857/S0207401X22100089
QR
Translate

Индексирование

Scopus

Scopus

Scopus

Crossref

Scopus

Higher Attestation Commission

At the Ministry of Education and Science of the Russian Federation

Scopus

Scientific Electronic Library