Conclusions
-
1.
The protolysis of phenylmercury bromide by hydrogen chloride in aqueous dioxane in the presence of sodium iodide is accomplished according to different mechanisms, depending upon the water content in the solvent.
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2.
In 90–95% dioxane, protolysis proceeds according to an SE2 mechanism, through a closed transition state.
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3.
In 80–60% dioxane, protolysis proceeds according to an SE1 mechanism, complicated by acid catalysis, accomplished by ion pairs of the acid.
-
4.
An approximate calculation of the kinetics in the transition region (85% dioxane) was undertaken.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 238–245, February, 1967.
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Beletskaya, I.P., Myshkin, A.E. & Reutov, O.A. Electrophilic substitution of the aromatic carbon atom. Russ Chem Bull 16, 232–238 (1967). https://doi.org/10.1007/BF00912419
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DOI: https://doi.org/10.1007/BF00912419