Oxygen-18 Exchange in Nitrophenols: Significance for Labeling and IsotopeEffect Experiments
Journal of the American Chemical Society
Nitrophenols labeled with 18O at the phenolic oxygen atom have found use in spectroscopic studies and in the measurement of 18O isotope effects.1 In addition, the formation of these species in hydrolysis reactions of nitrophenyl esters and phosphates has been used as a mechanistic probe to determine the position of bond cleavage.2 Nitro-substituted phenols have been reported to undergo only partial exchange of the phenolic oxygen atom with water in the presence of acids or bases, and only then under very harsh conditions.3 This has led a number of researchers in need of 18O-labeled 2-, 3-, and 4-nitrophenol and 2,4-dinitrophenol to develop a number of synthetic routes to these compounds, some of them rather involved.1a-e
A. C. Hengge. “Oxygen-18 Exchange in Nitrophenols: Significance for Labeling and Isotope Effect Experiments.” J. Am. Chem. Soc.1991, 113, 2747-2748.