Accurate oxidation potentials of 40 benzene and biphenyl derivatives with heteroatom substituents

Pu Luo, Adam M. Feinberg, Gonzalo Guirado, Samir Farid, Joseph P. Dinnocenzo

Research output: Contribution to journalArticleResearchpeer-review

20 Citations (Scopus)

Abstract

© 2014 American Chemical Society. The redox equilibrium method was used to determine accurate oxidation potentials in acetonitrile for 40 heteroatom-substituted compounds. These include methoxy-substituted benzenes and biphenyls, aromatic amines, and substituted acetanilides. The redox equilibrium method allowed oxidation potentials to be determined with high precision (≥ ±6 mV). Whereas most of the relative oxidation potentials follow well-established chemical trends, interestingly, the oxidation potentials of substituted N-methylacetanilides were found to be higher than those of the corresponding acetanilides. Density functional theory calculations provided insight into the origin of these surprising results in terms of the preferred conformations of the amides versus their cation radicals.
Original languageEnglish
Pages (from-to)9297-9304
JournalJournal of Organic Chemistry
Volume79
Issue number19
DOIs
Publication statusPublished - 3 Oct 2014

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