Abstract
A kinetic study was conducted on base-catalyzed proton-deuteron-exchange reactions of several substituted phenols. The exchange rates were determined by using the two-bond isotope shifts (2Δ) on the carbons and pattern-fitting analyses of the 13C-NMR signals.
Phenoxide ion (PhO-) was recognized by 18C-NMR chemical shifts of the reactio n solution. The reaction rates observed were proportional to various concentrations of base catalysts.
The rate constants were found to be expressed additively with substituent para meters.
The parameters for the meta and para positions were also found to be line arly correlated to the Hammett's σ+ constants with slope ρ= -3.0.
