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Estimation of Enthalpies of Alkoxy Radical Formation and Bond Strengths in Alcohols and Ether

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Abstract

Kinetic data on the thermal decomposition of peroxides were analyzed, and energies of the O–O bond dissociation were calculated. Enthalpies of formation of various alkoxy radicals and peroxides were determined. The dissociation energies for the O–H bonds in alcohols and C–O bonds in ethers were estimated. Comparative analysis of literature and obtained data was performed.

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REFERENCES

  1. Luo, Y-R., Handbook of Bond Dissociation Energies in Organic Compounds, Boca Raton, FL: CRC, 2003.

    Google Scholar 

  2. Kondrat'ev, V.N., Konstanty skorosti gazofaznykh reaktsii (Rate Constants of Gas-Phase Reactions), Mos-cow: Nauka, 1971.

    Google Scholar 

  3. Takezaki, Y. and Takenchi, C., J.Chem.Phys., 1954, vol. 22, p. 1527.

    Google Scholar 

  4. Barker, J.H., Benson, S.W., and Golden, D.M., Int.J.Chem.Kinet., 1977, vol. 9, p. 31.

    Google Scholar 

  5. Batt, L. and Rattray, G.N., Int.J.Chem.Kinet., 1979, vol. 11, p. 1183.

    Google Scholar 

  6. Ogata, Y., Tomizawa, K., Furuta, K., and Kato, H., J.Chem.Soc., Perkin Trans., 1981, vol. 2, p. 110.

    Google Scholar 

  7. Ogata, Y. and Hayashi, E., Bull.Chem.Soc.Jpn., 1974, vol. 50, p. 323.

    Google Scholar 

  8. Ogata, Y., Tokagi, K., and Hayashi, E., J.Org.Chem., 1979, vol. 44, p. 856.

    Google Scholar 

  9. Moriya, K., Rep.Phys.Chem.Jpn., 1946, p. 143.

  10. Rebbert, R.E. and Laidler, K.J., J.Chem.Phys., 1952, vol. 20, p. 574.

    Google Scholar 

  11. Harrison, J.R., Ph.D.Thesis., London: Univ. of London, 1952.

    Google Scholar 

  12. Legget, C. and Thynne, J.C.J., Trans.Faraday Soc., 1967, vol. 63, p. 2504.

    Google Scholar 

  13. Pryor, W.A. and Pultinas, E.P., J.Am.Chem.Soc., 1963, vol. 85, p. 133.

    Google Scholar 

  14. East, R.L. and Phillips, L., J.Chem.Soc.A., 1970, p. 331.

  15. Pryor, W.A., Huston, D.M., Fiske, T.R., Rickering, T.L., and Ciuffarin, E., J.Am.Chem.Soc., 1964, vol. 86, p. 4237.

    Google Scholar 

  16. Hughes, G.A. and Phillips, L., J.Chem.Soc.A., 1967, p. 894.

  17. Pryor, W.A. and Kaplan, G.L., J.Am.Chem.Soc., 1964, vol. 86, p. 4234.

    Google Scholar 

  18. Sahetchian, K.A. and Rigny, R., J.Chem.Soc., Faraday Trans.2., vol. 83, p. 2035.

  19. Walker, R.F. and Phillips, L., J.Chem.Soc.A., 1968, vol. 9, p. 2103.

    Google Scholar 

  20. Zaitseva, V.V., Yurchenko, A.Yu., and Enaliev, V.D., Zh.Org.Khim., 1968, vol. 4, p. 1402.

    Google Scholar 

  21. Perona, M.J. and Golden, D.M., Int.J.Chem.Kinet., 1973, vol. 5, p. 55.

    Google Scholar 

  22. Mashnenko, O.M., Batog, A.E., Mironenko, N.Yu., and Romantsevich, M.K., Vysokomol.Soedin.B, 1968, vol. 10, p. 444.

    Google Scholar 

  23. Hendrickson, W.H., Nguyen, Ch.C., Nguyen, J.T., and Simons, K.T., Tetrahedron Lett., 1995, vol. 36, p. 7217.

    Google Scholar 

  24. Buxtion, C. and Wilmarth, W.K., J.Phys.Chem., 1963, vol. 67, p. 2835.

    Google Scholar 

  25. Livingston, R. and Zeldes, H., J.Chem.Phys., 1966, vol. 44, p. 1245.

    Google Scholar 

  26. Livingston, R., Dohrmann, J.K., and Zeldes, H., J.Chem.Phys., 1970, vol. 53, p. 2448.

    Google Scholar 

  27. Blake, A.R. and Kutschke, K.O., Can.J.Chem., 1952, vol. 37, p. 1462.

    Google Scholar 

  28. Mulcahy, M.F.R. and Williams, D.J., Austr.J.Chem., 1961, vol. 14, p. 534.

    Google Scholar 

  29. Batt, L. and Benson, S.W., J.Chem.Phys., 1962, vol. 36, p. 895.

    Google Scholar 

  30. Long, J. and Skirrow, G., Trans.Faraday Soc., 1968, vol. 58, p. 1403.

    Google Scholar 

  31. Shaw, D.H. and Pritchard, H.O., Can.J.Chem., 1968, vol. 46, p. 2721.

    Google Scholar 

  32. Ralley, J.H., Rust, F.F., and Vaughan, W.E., J.Am.Chem.Soc., 1948, vol. 40, p. 88.

    Google Scholar 

  33. Lewis, D.K., Can.J.Chem., 1976, vol. 54, p. 581.

    Google Scholar 

  34. Huyser, E.S. and Scoy, R.M., J.Org.Chem., 1968, vol. 33, p. 3524.

    Google Scholar 

  35. Walling, C. and Metzger, G., J.Am.Chem.Soc., 1959, vol. 81, no. 58, p. 5365.

    Google Scholar 

  36. Antonovskii, V.L. and Bezborodova, L.D., Zh.Fiz.Khim., 1970, vol. 44, p. 1224.

    Google Scholar 

  37. Smith, J.R.L., Nagatomi, E., Stead, A., Waddington, D.J., and Beviere, S.D., J.Chem.Soc., Perkin Trans. 2, 2000, p. 1193.

    Google Scholar 

  38. Walling, C. and Wait, H.P., J.Phys.Chem., 1967, vol. 71, p. 2361.

    Google Scholar 

  39. Kavun, S.M. and Buchachenko, A.L., Izv.Akad.Nauk SSSR, Ser.Khim., 1966, p. 1483.

  40. Denisov, E.T. and Solyanikov, V.M., Neftekhimiya, 1963, no. 3, p. 360.

  41. Offenbach, J.A. and Tobolsky, A.V., J.Am.Chem.Soc., 1957, vol. 79, p. 278.

    Google Scholar 

  42. Pryor, W.A., Lee, A., and Witt, C.E., J.Am.Chem.Soc., 1964, vol. 86, p. 4229.

    Google Scholar 

  43. Bailey, H.C. and Godin, G.W., Trans.Faraday Soc., 1956, vol. 52, p. 68.

    Google Scholar 

  44. Kharasch, M.S., Fono, A., and Nudenberg, W., J.Org.Chem., 1951, vol. 16, p. 105.

    Google Scholar 

  45. Ivanchenko, P.A., Kharitonov, V.V., and Denisov, E.T., Vysokomol.Soedin.A, 1969, no. 11, p. 1622.

  46. Dannenberg, E.M., Jordan, M.E., and Cole, H.M., J.Pol.Sci., 1958, vol. 31, p. 127.

    Google Scholar 

  47. Thomas, D.K., J.Appl.Pol.Sci., 1963, vol. 6, p. 613.

    Google Scholar 

  48. Hoff, B.M.E., Ind.Eng.Chem.Product Res.Dev., 1963, no. 2, p. 273.

  49. Shilov, Yu.B., Cand.Sci.(Chem.) Dissertation, Cher-nogolovka: Inst. Chem. Phys., 1979.

  50. Shilov, Yu.B. and Denisov, E.T., Vysokomol.Soedin.A, 1978, vol. 20, p. 1849.

    Google Scholar 

  51. Griva, A.P. and Denisov, E.T., Kinet.Katal., 1976, vol. 17, p. 1465.

    Google Scholar 

  52. Matsuyama, K. and Higuchi, Y., Bull.Chem.Soc.Jpn., 1971, vol. 64, p. 259.

    Google Scholar 

  53. Ustinova, A.M., Cand.Sci.(Chem.) Dissertation, Donetsk: Donets State Univ., 1974.

    Google Scholar 

  54. Turovskii, N.A., Cand.Sci.(Chem.) Dissertation, Donetsk: Inst. Phys.-Org. Chem., 1978.

    Google Scholar 

  55. NIST Standard Reference Database 19A. Positive Ion Energetics, version 2.02. 1994.

  56. Tumanov, V.E. and Denisov, E.T., Neftekhimiya, 2001, vol. 41, no. 2, p. 108.

    Google Scholar 

  57. Tumanov, V.E., Kromkin, E.A., and Denisov, E.T., Izv.Akad Nauk, Ser.Khim., 2002, no. 9, p. 1508.

  58. Benson, S.W., Thermochemical Kinetics, New York: Wiley, 1968.

    Google Scholar 

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Tumanov, V.E., Denisov, E.T. Estimation of Enthalpies of Alkoxy Radical Formation and Bond Strengths in Alcohols and Ether. Kinetics and Catalysis 45, 621–627 (2004). https://doi.org/10.1023/B:KICA.0000044971.14314.36

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