Acetylenic alcohols—ynols—and acetylenic amines—ynamines—have been generated in aqueous solution by flash phololytic decarbonylation of hydroxy- and aminocyclopropenones and their chemistry has been examined in that medium. This has revealed a remarkably strong acid-strengthening effect of the acetylenic group, which ab initio molecular orbital calculations suggest results from a combination of destabilizing inductive effects on the initial state and stabilizing resonance effects on the final state of the acid ionization reaction.
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Chiang et al. (1996) studied this question.
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