Abstract
The protolytic equilibrium constants of chalcone and its furan and thiophene analogs have been measured spectrophotometrically in sulfuric acid — glacial acetic acid solution. It is shown that the furan ketones are more basic than the thiophene ones, basicity depending on the position of the carbonyl group in the conjugated chain. In the systems studied, 2-furyl exhibits an appreciably greater positive dynamical conjugation effect than 2-thienyl, but as compared with the latter it gives rise to less steric hindrance to solvation of carbonium ions.
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