Abstract
The pK values of a series of substituted pyrroles and the ΔvNH values (in dimethylformamide), which characterize their relative acidities were measured by the transmetallation method. It was established that the acidities of pyrroles are determined primarily by the inductive effect of the substituents and are virtually independent of the ability of the latter to enter into conjugation with the ring. This means that the electron pair of the anion that is set free in the ionization of pyrrole retains σ character. The linear dependences of the pK and ΔυNH values on the inductive constants (σI) of the substituents can be used to estimate the pK values of various compounds that contain a pyrrole ring starting from the ΔυNH and σI values.
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See [1] for communication 13.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 632–638, May, 1980.
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Trofimov, B.A., Shatenshtein, A.I., Petrov, É.S. et al. Pyrroles from ketoximes and acetylene. 14. Quantitative estimate of the effect of substituents on the NH acidities of pyrroles. Chem Heterocycl Compd 16, 488–495 (1980). https://doi.org/10.1007/BF00561346
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DOI: https://doi.org/10.1007/BF00561346