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Luo P, Feinberg EC, Guirado G, et al. Accurate oxidation potentials of 40 benzene and biphenyl derivatives with heteroatom substituents. J Org Chem. 2014;79(19):9297-304doi: 10.1021/jo501761c.
Luo, P., Feinberg, E. C., Guirado, G., Farid, S., & Dinnocenzo, J. P. (2014). Accurate oxidation potentials of 40 benzene and biphenyl derivatives with heteroatom substituents. The Journal of organic chemistry, 79(19), 9297-304. https://doi.org/10.1021/jo501761c
Luo, Pu, et al. "Accurate oxidation potentials of 40 benzene and biphenyl derivatives with heteroatom substituents." The Journal of organic chemistry vol. 79,19 (2014): 9297-304. doi: https://doi.org/10.1021/jo501761c
Luo P, Feinberg EC, Guirado G, Farid S, Dinnocenzo JP. Accurate oxidation potentials of 40 benzene and biphenyl derivatives with heteroatom substituents. J Org Chem. 2014 Oct 03;79(19):9297-304. doi: 10.1021/jo501761c. Epub 2014 Sep 17. PMID: 25184671.
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J Org Chem. 2014 Oct 03;79(19):9297-304. doi: 10.1021/jo501761c. Epub 2014 Sep 17.

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

The Journal of organic chemistry

Pu Luo, Elizabeth C Feinberg, Gonzalo Guirado, Samir Farid, Joseph P Dinnocenzo

Affiliations

  1. Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.

PMID: 25184671 DOI: 10.1021/jo501761c

Abstract

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.

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