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Cited by 308

The DOI matches its Crossref record; 51 of the 51 references it cites were found in a registry or an index.

Quinone 1 e– and 2 e–/2 H+ Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships

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Huynh, Mioy T., Anson, Colin W., Cavell, Andrew C., Stahl, Shannon S., Hammes-Schiffer, Sharon·2016·Journal of the American Chemical Society
DOI 10.1021/jacs.6b05797
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Abstract

Quinones participate in diverse electron transfer and proton-coupled electron transfer processes in chemistry and biology. To understand the relationship between these redox processes, an experimental study was carried out to probe the 1 e – and 2 e – /2 H + reduction potentials of a number of common quinones. The results reveal a non-linear correlation between the 1 e – and 2 e – /2 H + reduction potentials. This unexpected observation prompted a computational study of 134 different quinones, probing their 1 e – reduction potentials, p K a values, and 2 e – /2 H + reduction potentials. The density functional theory calculations reveal an approximately linear correlation between these three properties and an effective Hammett constant associated with the quinone substituent(s). However, deviations from this linear scaling relationship are evident for quinones that feature intramolecular hydrogen bonding, halogen substituents, charged substituents, and/or sterically bulky substituents. These results, particularly the different substituent effects on the 1 e – versus 2 e – /2 H + reduction potentials, have important implications for designing quinones with tailored redox properties.

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Metadata

Authors
Huynh, M. T., Anson, C. W., Cavell, A. C., Stahl, S. S., & Hammes-Schiffer, S.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2016-11-30
Volume
138
Issue
49
Pages
15903-15910
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/jacs.6b05797
OpenAlex
W2549621674
Cited by
308
References
51
FWCI
7.57
Type
journal article
Language
en
Open access
green

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