Abstract
The protolytic equilibrium constants in the system H2SO4-CH3COOH and the shifts in frequency of the OH stretching vibrations (Δν OH) of phenol and trifluoroacetic acid resulting from the perturbational effects of hydrogen bonding with the carbonyl group have been measured for α-alkyl-substituted heterocyclic analogs of chalcone. It has been shown that introduction of a methyl group into the α-position of five-membered heterocycles results in an increase in the proton-acceptor properties of chalcone analogs, and moreover, the influence of the methyl group on the polarization of the carbonyl group is substantially increased on passing from the furan ring to the hiophene and selephene rings, perhaps as a result of the participation of the d-orbitals of sulfur and selenium in the electronic interactions. The benzene ring transmits the electronic effect of the methyl group to almost the same extent as the furan ring.
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For Part VI, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1176–1180, September, 1970.
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Tsukerman, S.V., Kutulya, L.A., Surov, Y.N. et al. Basicity and structure of α,β-unsaturated heterocyclic ketones. Chem Heterocycl Compd 6, 1097–1100 (1970). https://doi.org/10.1007/BF00480712
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DOI: https://doi.org/10.1007/BF00480712