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