REACTIVE SPECIES - YNOLS AND YNAMINES

Acetylenic alcohols-ynols-and acetylenic amines-ynamines-have been gen erated in aqueous solution by flash phololytic decarbonylation of hydr oxy- 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 cal culations suggest results from a combination of destabilizing inductiv e effects on the initial state and stabilizing resonance effects on th e final state of the acid ionization reaction.