Conclusions
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1.
The rates of triplet quenching of anthraquinone by substituted anilines and phenols and their OH- and NH2-deuterated analogs have been measured by pulse photolysis in toluene and acetonitrile solutions.
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2.
In the case of anilines the kinetics of hydrogen atom transfer are determined by charge transfer in the transition state or by the formation of charge transfer complexes as intermediates in these reactions. The kinetic isotope effect for these reactions is increased up to five as the anthraquinone triplet quenching rate constants are decreased as a function of reduced electron-donating ability of substituted anilines.
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3.
The kinetic isotope effect for hydrogen atom transfer reactions from substituted phenols to the triplet state of anthraquinone reaches a maximum of two and is determined not only by the degree of charge transfer in the transition state but also by the kinetics of formation of an intermediate hydrogen-bonded complex.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1007–1011, May, 1988.
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Belyaev, A.B., Kuz'min, V.A. & Levin, P.P. Kinetic isotope effect for hydrogen atom transfer from substituted anilines and phenols to the triplet state of anthraquinone. Russ Chem Bull 37, 877–881 (1988). https://doi.org/10.1007/BF00957050
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DOI: https://doi.org/10.1007/BF00957050