Appendix B
Tables of Physical Data
Table B.1 Potential window of organic solution for electrochemical reactions
(Pt working electrode)
Solvent
Supporting electrolyte
Potential (V vs. SCE)
Cathodic side
AcOH
Acetone
MeCN
MeCN
DMF
DMSO
MeOH
MeOH
CH2Cl2
THF
Sulfolane
MeNO2
Propylene carbonate
AcONa
n-Bu4NClO4
LiClO4
Et4NBF4
n-BuN4ClO4
LiClO4
LiClO4
KOH
n-BuN4ClO4
LiClO4
NaClO4
Mg(ClO4)2
Et4ClO4
1.0
1.0
3.0
1.8
2.8
3.8
1.0
1.0
1.7
3.2
4.0
2.6
1.9
Anodic side
+2.0
+1.6
+2.5
+3.2
+1.6
+1.3
+1.3
+0.6
+1.8
+1.6
+2.3
+2.2
+1.7
Fundamentals and Applications of Organic Electrochemistry: Synthesis, Materials, Devices,
First Edition. Toshio Fuchigami, Mahito Atobe and Shinsuke Inagi.
© 2015 John Wiley & Sons, Ltd. Published 2015 by John Wiley & Sons, Ltd.
218
Appendix B: Tables of Physical Data
Table B.2 Oxidation potentials of typical organic compounds
Compound
Aromatic compounds
Benzene
Toluene
Anisole
Biphenyl
Fluorene
Naphthalene
Pyridine
Thiophene
Pyrrole
Olefins
Ethylene
Cyclohexene
Styrene
Nitrogen and sulfur
compounds
Acetamide
Aniline
N-Methylaniline
Nitrobenzene
Thiophenol
Dimethyl sulfide
Diphenyl disulfide
Alcohols
Methanol
Ethanol
Isopropyl alcohol
t-Butyl alconol
Ally alcohol
Benzyl alcohol
Phenol
Electrolyte/solvent
Potential (V)
Reference
electrode
NaClO4/MeCN
NaClO4/MeCN
Pr4NClO4/MeCN
NaClO4/MeCN
NaClO4/MeCN
NaClO4/MeCN
NaClO4/MeCN
NaClO4/MeCN
NaClO4/MeCN
2.00
1.93
1.76
1.48
1.25
1.31
2.2
2.10
0.46
Ag/Ag+
Ag/Ag+
SCE
Ag/Ag+
Ag/Ag+
SCE
SCE
SCE
SCE
Bu4NBF4/MeCN
NaClO4/MeCN
NaClO4/MeCN
2.90
1.95
1.90
Ag/Ag+
Ag/Ag+
SCE
Et4NClO4/MeCN
Buffer/H2O
Na2SO4/H2O
0.1 M HCl/50%
acetone/H2O
CF3CO2H/CH2Cl2
0.1 M HCl/MeOH
LiClO4/MeCN/CH2Cl2
2.00
1.04
0.70
0.58
SCE
SCE
SCE
NHE
1.65
0.86
1.75
Ag/Ag+
Ag/Ag+
Ag/Ag+
2.73
2.61
2.50
2.60
2.65
>2.00
1.04
Fc/Fc+
Fc/Fc+
Fc/Fc+
Fc/Fc+
Fc/Fc+
Ag/Ag+
Ag/Ag+
Bu4NBF4/MeCN
Bu4NBF4/MeCN
Bu4NBF4/MeCN
Bu4NBF4/MeCN
Bu4NBF4/MeCN
NaClO4/MeCN
NaClO4/MeCN
Appendix B: Tables of Physical Data
219
Table B.3 Reduction potentials of typical organic compounds
Compound
Halogen compounds
Chloromethane
t-Butyl chloride
t-Butyl bromide
t-Butyl iodide
Carbonyl compounds
Acetone
Acetophenone
Formaldehyde
Acetaldehyde
Benzaldehyde
Quinones
1,4-Benzoquinone
1,4-Naphtoquinone
9,10-Anthraquinone
Olefins
Styrene
trans-Stilbene
cis-Stilbene
Aromatic compounds
Benzene
Naphthalene
Anthracene
Pyrene
Biphenyl
Furfural
2,6-Dimethylpyridine
Nicotinamide
Nitrogen and sulfur
compounds
Nitromethane
Nitrobenzene
Diphenyl disulfide
Methyl phenyl sulfone
Benzenesulfonic acid
Electrolyte/solvent
Potential (V)
Reference
electrode
Et4NClO4/DMF
Et4NClO4/DMF
Et4NBr/DMF
Bu4NBF4/DMF
2.76
2.60
2.19
1.91
SCE
SCE
SCE
SCE
Et4NBr/DMF
LiOH/75% Dioxane
pH = 8
pH = 9.1
NH4Cl/40% EtOH
2.84
1.26
1.22
1.51
1.32
SCE
SCE
NHE
NHE
SCE
50% EtOH
50% EtOH
95% EtOH
0.71
0.49
0.16
NHE
NHE
NHE
Bu4NI/DMF
Bu4NI/DMF
Bu4NI/DMF
2.45
2.30
2.07
SCE
SCE
SCE
Bu4NBr/Me2NH
Bu4NBr/Me2NH
Bu4NBr/Me2NH
Bu4NBr/Me2NH
NaBPh4/THF
Britton and Robinson/
H2 O
Bu4NI/DMF
Britton and Robinson/
MeOH
3.42
2.53
2.04
2.29
2.68
1.04
Ag/Ag+
Ag/Ag+
Ag/Ag+
Ag/Ag+
Ag/Ag+
SCE
2.85
1.34
Ag/Ag+
Ag/Ag+
pH = 7/H2O
pH = 7/80% dioxane
Bu4NI/DMF
Bu4NBr/DMF
Me4NCl/dioxane
0.88
0.62
2.75
2.41
1.50
SCE
SCE
Ag/Ag+
SCE
SCE
Appendix B: Tables of Physical Data
Figure B.1 Electrode potential regions for reduction of functional groups
Figure B.2 Electrode potential regions for oxidation of functional groups
221