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Kinetics and Mechanism of Monomolecular Heterolysis of Cage-Like Compounds: XVIII. Solvent Effect on the Rate of Heterolysis of 3-Bromocyclohexene. Correlation Analysis of Solvation Effects

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Abstract

The kinetics of E1 dehydrobromination of 3-bromocyclohexene in 23 aprotic and 9 protic solvents were studied by the verdazyl technique. The reaction rate is described by the polarity, electrophilicity, and ionizing power parameters of the solvent. Nucleophilicity, polarizability, and cohesion parameters of the solvent do not affect the reaction rate. The effects of equilibrium and nonequilibrium solvation of the transition state are discussed.

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Authors and Affiliations

  1. “Kievskii politekhnicheskii institut”, National Technical University of Ukraine, pr. Peremogi 37, Kiev, 03056, Ukraine

    N. E. Ponomarev, M. V. Stambirskii, G. F. Dvorko & A. V. Bazil’chuk

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  1. N. E. Ponomarev
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  2. M. V. Stambirskii
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  3. G. F. Dvorko
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  4. A. V. Bazil’chuk
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Ponomarev, N.E., Stambirskii, M.V., Dvorko, G.F. et al. Kinetics and Mechanism of Monomolecular Heterolysis of Cage-Like Compounds: XVIII. Solvent Effect on the Rate of Heterolysis of 3-Bromocyclohexene. Correlation Analysis of Solvation Effects. Russian Journal of Organic Chemistry 40, 489–496 (2004). https://doi.org/10.1023/B:RUJO.0000036068.58478.e4

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