Work

Structural Effects on the pH-Dependent Redox Properties of Organic Nitroxyls: Pourbaix Diagrams for TEMPO, ABNO, and Three TEMPO Analogs

Year: 2017

Type: article

Abstract: Electrochemical studies of the reduction and oxidation reactions of five different organic nitroxyls have been performed across a wide pH range (0–13). The resulting Pourbaix diagrams illustrate structural effects on their various redox potentials and on the p K a values of the corresponding hydroxylamine and hydroxylammonium ions. Evidence is also given for the reversible formation of a hydroxylamine N -oxide when nitroxyls are oxidized in alkaline media. Structural effects on the thermodynamics of this reaction are assessed.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.7b02547

Authors: James B. Gerken, Yutong Q. Pang, Markus B. Lauber, Shannon S. Stahl

Institution: University of Wisconsin–Madison

Language: English

Topic: Free Radicals and Antioxidants

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green