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Section: 5 | Reduction and Oxidation Potentials for Ion Radicals |
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John R. Rumble, ed., CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021), CRC Press/Taylor & Francis, Boca Raton, FL.
If a specific table is cited, use the format: "Physical Constants of Organic Compounds," in CRC Handbook of Chemistry and Physics, 102nd Edition (Internet Version 2021), John R. Rumble, ed., CRC Press/Taylor & Francis, Boca Raton, FL.

REDUCTION AND OXIDATION POTENTIALS FOR ION RADICALS

Petr Vanýsek

There are two tables for ion radicals. The first table lists reduction potentials for organic compounds that produce anion radicals during reduction, a process described as A + e- ⇌ A-·. The second table lists oxidation potentials for organic compounds that produce cation radicals during oxidation, a process described as A ⇌ A+· + e-. To obtain reduction potential for a reverse reaction, the sign for the potential is changed.

Unlike the table of the Electrochemical Series, which lists standard potentials, values for radicals are experimental values with experimental conditions given in the second column. Because the measurements leading to potentials for ion radicals are very dependent on conditions, an attempt to report standard potentials for radicals would serve no useful purpose. For the same reason, the potentials are also reported as experimental values, usually a half-wave potential (E1/2 in polarography) or a peak potential (Ep in cyclic voltammetry). Unless otherwise stated, the values are reported versus SCE (saturated calomel electrode). To obtain a value versus normal hydrogen electrode, 0.241 V has to be added to the SCE values. All the ion radicals chosen for inclusion in the tables result from electrochemically reversible reactions. More detailed data on ion radicals can be found in the Encyclopedia of Electrochemistry of Elements, (A. J. Bard, Ed.), Vols. XI and XII in particular, Marcel Dekker, New York, 1978.

Abbreviations are:

  

CV cyclic voltammetry
DMF N,N-Dimethylformamide
E swp potential sweep
E° standard potential
Ep peak potential
Ep/2 half-peak potential
E1/2 half-wave potential
M mol/L
MeCN acetonitrile
pol polarography
rot Pt dsk rotated Pt disk
SCE saturated calomel electrode
TBABF4 tetrabutylammonium tetrafluoroborate
TBAI tetrabutylammonium iodide
TBAP tetrabutylammonium perchlorate
TEABr tetraethylammonium bromide
TEAP tetraethylammonium perchlorate
THF tetrahydrofuran
TPACF3SO3 tetrapropylammonium trifluoromethanesulfite
TPAP tetrapropylammonium perchlorate
wr wire
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Mobile-friendly table

TABLE 1. Reduction Potentials for Products That Are Anion Radicals



NameConditions/electrode/techniquePotential V (vs. SCE)
Continued on next page...
AcetoneDMF, 0.1 M TEABr/Hg/polE1/2 = –2.84
1-NaphthyphenylacetyleneDMF, 0.03 M TBAI/Hg/polE1/2 = –1.91
1-Naphthalenecarboxyaldehyde-/Hg/polE1/2 = –0.91
2-Naphthalenecarboxyaldehyde-/Hg/polE1/2 = –0.96
2-Phenanthrenecarboxaldehyde-/Hg/polE1/2 = –1.00
3-Phenanthrenecarboxaldehyde-/Hg/polE1/2 = –0.94
9-Phenanthrenecarboxaldehyde-/Hg/polE1/2 = –0.83
1-Anthracenecarboxaldehyde-/Hg/polE1/2 = –0.75
1-Pyrenecarboxaldehyde-/Hg/polE1/2 = –0.76
2-Pyrenecarboxaldehyde-/Hg/polE1/2 = –1.00
AnthraceneDMF, 0.1 M TBAP/Pt dsk/CVEp = –2.00
DMF, 0.5 M TBABF4/Hg/CVE1/2 = –1.93
MeCN, 0.1 M TEAP/Hg/CVE1/2 = –2.07
DMF, 0.1 M TBAI/Hg/polE1/2 = –1.92
9,10-DimethylanthraceneDMF, 0.1 M TBAP/Pt/CVEp = –2.08
MeCN, 0.1 M TBAP/Pt/CVEp = –2.10
1-PhenylanthraceneDMF, 0.5 M TBABF2/Hg/CVE1/2 = –1.91
DMF, 0.1 M TBAI/Hg/polE1/2 = –1.878
2-PhenylanthraceneDMF, 0.1 M TBAI/Hg/polE1/2 = –1.875

  • avs. 0.01 M Ag/AgClO4
  • bvs. Hg/Hg2SO4, 17 M H2SO4
  • cvs. Hg pool
  • dvs. Ag/0.01 M Ag+


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