Oxygen-18 Exchange in Nitrophenols: Significance for Labeling and IsotopeEffect Experiments

Authors

Alvan C. Hengge, Utah State UniversityFollow

Document Type

Article

Journal/Book Title

Journal of the American Chemical Society

Publication Date

1991

Volume

113

First Page

2747

Last Page

2748

Abstract

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

Recommended Citation

A. C. Hengge. “Oxygen-18 Exchange in Nitrophenols: Significance for Labeling and Isotope Effect Experiments.” J. Am. Chem. Soc.1991, 113, 2747-2748.