Abstract
The protolytic equilibrium constants of five pyrrole and three indole analogs of the chalcones in the H2SO4-CH3COOH system have been determined spectrophotometrically. The electronic influences of the 2-pyrryl, N-methyl-2-pyrryl, indol-3-yl, and N-methylindol-3-yl groups have been evaluated quantitatively by means of their σ+ parameters which are, respectively: −2.10, −2.07, −2.25, and −2.28. It has been shown that in α, β-unsaturated ketones the nitrogen-containing heterocyclic radicals 2-pyrryl and indol-3-yl, and also their N-methyl derivatives, exhibit a positive dynamic conjugation effect considerably exceeding that for 2-furyl, 2-thienyl, and 2-selenienyl.
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For part V, see [12].
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Tsukerman, S.V., Kutulya, L.A. & Lavrushin, V.F. Basicity and structure of α,β-unsaturated ketones of the heterocyclic series. Chem Heterocycl Compd 5, 741–745 (1972). https://doi.org/10.1007/BF00475844
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DOI: https://doi.org/10.1007/BF00475844