Abstract
The enthalpies, activation energies, and rate constants of the reactions of thio (amino) alkylphenols of different structures were calculated and compared with those of the reactions of alkyl-substituted phenols, alkoxyl and alkyl radicals, hydroperoxides, and nitrogen dioxide, as well as the reactions of phenoxyl radicals with molecules of the substrate being oxidized. The calculation was performed by the intersecting parabolas method using O-H bond energy data for phenols. The correlation between the molecular structure of the thio (amino) alkylphenols and their reactivity in radical reactions is considered.
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Terakh, E.I., Pinko, P.I., Zaitseva, O.V., and Prosenko, A.E., Russ. J. Appl. Chem., 2003, vol. 76, no. 9, p. 1494.
Terakh, E.I, Kandalintseva, N.V., Nikulina, V.V., Pinko, P.I., and Prosenko, A.E., Pet. Chem., 2004, vol. 43, no. 3, p. 211.
Terakh, E.I., Cand. Sci. (Chem.) Dissertation, Novosibirsk: Novosibirsk State Pedagogical Univ., 2004.
Dyubchenko, O.I., Nikulina, V.V., Terakh, E.I., Prosenko, A.E., and Grigor’ev, I.A., Russ. J. Appl. Chem., 2005, vol. 78, no. 5, p. 791.
Prosenko, A.E., Markov, A.F., Khomchenko, A.S., Boiko, M.A., Terakh, E.I., and Kandalintseva, N.V., Pet. Chem., 2006, vol. 46, no. 6, p. 442.
Prosenko, A.E., Dyubchenko, O.I., Terakh, E.I., Markov, A.F., Gorokh, E.A., and Boiko, M.A., Pet. Chem., 2006, vol. 46, no. 4, p. 283.
Dyubchenko, O.I., Nikulina, V.V., Terakh, E.I., Prosenko, A.E., and Grigor’ev, I.A., Russ. Chem. Bull., 2007, vol. 56, no. 6, p. 1149.
Khomchenko, A.S., Kravtsov, S.O., Boiko, M.A., and Prosenko, A.E., Khim. Interes. Ust. Razv., 2008, no. 16, p. 133.
Boiko, M.A., Terakh, E.I., and Prosenko, A.E., Kinet. Catal., 2006, vol. 47, no. 5, p. 677.
Boiko, M.A., Terakh, E.I., and Prosenko, A.E., Russ. J. Phys. Chem., 2006, vol. 80, no. 8, p. 1225.
Boiko, M.A., Extended Abstract of Cand. Sci. (Chem.) Dissertation, Novosibirsk: Novosibirsk State Pedagogical Univ., 2006.
Terakh, E.I., Al’manakh Sovrem. Nauki Obraz., 2010, vol. 40, no. 9, p. 85.
Denisov, E.T. and Denisova, T.G., Usp. Khim., 2009, vol. 78, no. 11, p. 1129.
Denisov, E.T., Usp. Khim., 1997, vol. 66, no. 10, p. 953.
Denisov, E.T. and Tumanov, E.T., Usp. Khim., 2005, vol. 74, no. 9, p. 905.
Denisova, T.G., Doctoral (Chem.) Dissertation, Chernogolovka, Moscow oblast: Inst. of Problems of Chemical Physics, 2006.
Denisova, T.G. and Denisov, E.T., Kinet. Catal., 2009, vol. 50, no. 3, p. 335.
Denisov, E.T. and Denisova, T.G., Handbook of antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions, Boca Raton, Fla.: CRC, 2000.
Terakh, E.I., in Aktual’nye voprosy sovremennoi nauki (Topics in Contemporary Science), vol. 18, Novosibirsk: Novosibirsk. Gos. Tekh. Univ., 2011, p. 16.
Roginskii, V.A., Fenol’nye antioksidanty: Reaktsionnaya sposobnost’ i effektivnost’ (Phenolic Antioxidants: Reactivity and Efficiency), Moscow: Nauka, 1988.
Lissi, E.A., Collados, J., and Olea, A., Int. J. Chem. Kinet., 1985, vol. 17, no. 3, p. 265.
Chateauneuf, J., Lusztyk, J., and Ingold, K.U., J. Am. Chem. Soc., 1988, vol. 110, no. 9, p. 2877.
Bors, W., J. Phys. Chem., 1987, vol. 91, no. 9, p. 2362.
Heer, M.I., Mulder, P., Korth, H.-G., Ingold, K.U., and Lusztyk, J., J. Am. Chem. Soc., 2000, vol. 122, no. 10, p. 2355.
Das, P.K., Encinas, M.V., Steenken, S., and Scaiano, J.C., J. Am. Chem. Soc., 1981, vol. 103, no. 14, p. 4162.
Martem’yanov, V.S., Denisov, E.T., and Samoilova, L.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1972, no. 5, p. 1039.
Emanuel’, N.M., Denisov, E.T., and Maizus, Z.K., Tsepnye reaktsii okisleniya uglevodorodov v zhidkoi faze (Chain Liquid-Phase Oxidation of Hydrocarbons), Moscow: Nauka, 1975.
Zenkov, N.K., Lankin, V.Z., and Men’shchikova, E.B., Okislitel’nyi stress: Biokhimicheskii i patofiziologicheskii aspekty (Oxidative Stress: Biochemical and Pathophysiological Aspects), Moscow: Nauka, 2001.
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Original Russian Text © E.I. Terakh, A.E. Prosenko, 2012, published in Kinetika i Kataliz, 2012, Vol. 53, No. 5, pp. 563–569.
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Terakh, E.I., Prosenko, A.E. Reactivity of thio (amino) derivatives of the ω-(4-hydroxyaryl)alkyl type in radical reactions. Kinet Catal 53, 537–542 (2012). https://doi.org/10.1134/S002315841205014X
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DOI: https://doi.org/10.1134/S002315841205014X