Abstract
The temperature dependences of the equilibrium constants of two chain reversible reactions in quinonediimine (quinonemonoimine)—2,5-dichlorohydroquinone systems in chlorobenzene were studied. The enthalpy of equilibrium of the reversible reaction of quinonediimine with 4-hydroxydiphenylamine was estimated from these data (ΔH = − 14.4±1.6 kJ mol−1) and a more accurate value of the N-H bond dissociation energy in the 4-anilinodiphenylaminyl radical was determined (D NH = 278.6±3.0 kJ mol−1). A chain mechanism was proposed for the reaction between quinonediimine and 2,5-dichlorohydroquinone, and the chain length was estimated (ν = 300 units) at room temperature. Processing of published data on the rate constant of the reaction of styrylperoxy radicals with 2,5-dichlorohydroquinone in the framework of the intersecting parabolas method gave the O-H bond dissociation energy in 2,5-dichlorohydroquinone: D OH = 362.4±0.9 kJ mol−1. Taking into account these data, the O-H bond dissociation energy in the 2,5-dichlorosemiquinone radical was found: D OH = 253.6±1.9 kJ mol−1.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1661–1666, October, 2006.
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Antonov, A.V., Gadomsky, S.Y. & Varlamov, V.T. Determination of dissociation energies of N-H bond in the 4-anilinodiphenylaminyl radical and O-H bond in the 2,5-dichloro-4-hydroxyphenoxyl radical from the equilibrium constants of chain reactions in quinoneimine-hydroquinone systems. Russ Chem Bull 55, 1723–1728 (2006). https://doi.org/10.1007/s11172-006-0479-5
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DOI: https://doi.org/10.1007/s11172-006-0479-5