Abstract
The dissociation energies of O-H bonds (D O-H) of 48 phenol sulfides and N-H bonds (D N-H) of five amino sulfides were determined from experimental data. The dissociation energies of the bonds were estimated by the method of crossing parabolas from the kinetic data (the rate constants of reactions of peroxyl radicals with these antioxidants). The O-H, S-H, and N-H bond dissociation energies were determined for three hybrid antioxidants (two hydroxythiophenols and one aminophenol): D O-H = 335.9 kJ mol−1 and D S-H = 340.8 kJ mol−1 for 2-hydroxy-3,5-bis-(1′-phenylethyl)thiophenol, D O-H = 337.7 kJ mol−1 and D S-H = 344.2 kJ mol−1 for 3,5-bis-(1′-phenylethyl)-4-hydroxythiophenol, and D O-H = 338.6 kJ mol−1 and D N-H = 366.2 kJ mol−1 for 1-(N-phenylamino)-2-thiol-3-thio-(3′,5′-bis-di-tert-butyl-4′-hydroxyphenyl)-propane.
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References
A. M. Kuliev, Chemistry and Technology of Oil and Fuel Additives (Khimiya, Leningrad, 1985) [in Russian].
E. T. Denisov and I. B. Afanas’ev, Oxidation and Antioxidants in Organic Chemistry and Biology (CRC, Boca Raton, FL, 2005).
E. T. Denisov and T. G. Denisova, Handbook of Antioxidants. Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions (CRC, Boca Raton, FL, 2000).
E. T. Denisov, T. G. Denisova, S. V. Trepalin, and T. I. Drozdova, Data Base of Oxidation and Antioxidants in Organic Chemistry (CRC, Boca Raton, FL, 2005).
Y. R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds (CRC, Boca Raton, FL, 2003).
E. T. Denisov and T. G. Denisova, Application of Thermodynamics to Biological and Materials Science, Ed. by T. Mizutani (InTech, Rijeka, 2011), p. 405.
E. T. Denisov, Russ. Chem. Rev. 66, 859 (1997).
E. T. Denisov, Zh. Fiz. Khim. 67, 2416 (1993).
E. T. Denisov, Zh. Fiz. Khim. 69, 623 (1995).
E. Denisov, C. Chatgilialoglu, A. F. Shestakov, and T. G. Denisova, Int. J. Chem. Kinet. 41, 284 (2009).
J. H. B. Chenier, E. Furimsky, and J. A. Howard, Can. J. Chem. 52, 3682 (1974).
F. A. Kuliev, V. M. Farzaliev, and M. G. Voronkov, Neftekhimiya 21, 607 (1981).
A. S. Aliev, Extended Abstract of Candidate’s Dissertation in Chemistry (Baku, 1975) [in Russian].
A. D. Aslanov, N. V. Zolotova, E. T. Denisov, and F. A. Kuliev, Neftekhimiya 22, 394 (1982).
V. M. Farzaliev, F. A. Kuliev, M. M. Akhundova, and E. T. Denisov, Azerb. Khim. Zh, No. 4, 117 (1981).
O. A. Raevsky, V. Yu. Grigor’ev, D. B. Kireev, and N. S. Zefirov, Quant. Struct. Act. Relat. 11, 49 (1992).
V. E. Tumanov and E. T. Denisov, Butlerovsk. Soobshch. 32(10), 55 (2012).
P. Sh. Mamedova, Extended Abstract of Doctoral Dissertation in Chemistry (Baku, 1992).
Ch. I. Mamedov, Extended Abstract of Candidate’s Dissertation in Chemistry (Baku, 1984).
M. Lucarini, G. F. Pedulli, and M. Cipollone, Org. Chem. 59, 5063 (1994).
V. Z. Lankin, V. A. Roginskii, F. K. Tikhadze, et al., Dokl. Akad. Nauk 351, 554 (1996).
M. A. Boiko, E. I. Terakh, and A. E. Prosenko, Russ. J. Phys. Chem. 80, 2025 (2006).
V. M. Farzaliev, M. A. Allakhverdiev, and I. A. Rzaeva, Pet. Chem. 38, 126 (1998).
E. T. Denisov and T. G. Denisova, Kinet. Katal. 54, 677 (2013).
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Original Russian Text © E.T. Denisov, T.G. Denisova, 2014, published in Neftekhimiya, 2014, Vol. 54, No. 2, pp. 146–157.
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Denisov, E.T., Denisova, T.G. Dissociation energies of O-H, N-H, and S-H bonds in sulfur-containing antioxidants. Pet. Chem. 54, 142–153 (2014). https://doi.org/10.1134/S0965544114010034
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DOI: https://doi.org/10.1134/S0965544114010034