General Base Catalyzed Hydrogen Exchange of 1-Octyne, 4-Nitrophenylacetylene, and 3-(Phenyldimethylammonio)-1-propyne. Broensted Relations and Normal Acid Behavior

Article abstract of DOI:10.1021/jo00356a012

Rates of loss of tritium from the title compounds labeled at the acetylenic hydrogen position were measured in aqueous primary amine buffer solutions at 25 deg C.These data give Broensted relations with essentially unit exponents: β = 0.97 +/- 0.06 for 1-octyne, β = 0.97 +/- 0.05 for 4-nitrophenylacetylene, and β = 0.98 +/- 0.05 for 3-(phenyldimethylammonio)-1-propyne, which indicates that these acetylenes are "normal" rather than pseudo carbon acids.