Formal redox potentials of organic molecules in ionic liquids on the basis of quaternary nitrogen cations as adiabatic electron affinities

Journal of Physical Chemistry B

Volumn 117, Issue 37, 2013, Pages 10834-10845

  Seto, Kunimasa ^a   Nakayama, Tatsushi ^b   Uno, Bunji ^a,b  

^a GIFU UNIVERSITY   (Japan)

^b GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONTINUUM MECHANICS; ELECTROLYTES; MOLECULES; NAPHTHALENE; POLYCYCLIC AROMATIC HYDROCARBONS; POSITIVE IONS; REDOX REACTIONS;

ADIABATIC ELECTRON AFFINITY; CONCENTRATION RANGES; ELECTROCHEMICAL STABILITIES; LOGARITHMIC RELATIONSHIP; MEASUREMENT CONDITIONS; POLARIZED CONTINUUM MODELS; POLYNUCLEAR AROMATIC HYDROCARBONS; SUPPORTING ELECTROLYTE;

IONIC LIQUIDS;

9,10-ANTHRAQUINONE; ANTHRAQUINONE; ANTHRAQUINONE DERIVATIVE; AROMATIC HYDROCARBON; BENZOQUINONE; BENZOQUINONE DERIVATIVE; ELECTROLYTE; IONIC LIQUID; NITROGEN; QUINONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMISTRY; ELECTRON; OXIDATION REDUCTION REACTION;

ANTHRAQUINONES; BENZOQUINONES; ELECTROLYTES; ELECTRONS; HYDROCARBONS, AROMATIC; IONIC LIQUIDS; NITROGEN; OXIDATION-REDUCTION; QUINONES; SOLVENTS;

EID: 84884524557     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp402457k     Document Type: Article

References (105)

1. Halliwell, B.; Gutteridge, J. M. C. Free Radical in Medicine and Biology, 3 rd ed.; Oxford University Press: New York, 1999.
2. Evans, D. H. One-Electron and Two-Electron Transfers in Electrochemistry and Homogeneous Solution Reactions Chem. Rev. 2008, 108, 2113-2144
3. Rempala, P.; Sheridan, R. S. Matrix Isolation and Photochemistry of 1- and 2-Naphthylchlorocarbene J. Chem. Soc., Perkin Trans. 2 1999, 2257-2265
4. Greatbanks, S. P.; Gready, J. E.; Limaye, A. C.; Rendell, A. P. Enzyme Polarization of Substrates of Dihydrofolate Reductase by Different Theoretical Methods Proteins: Struct., Funct., Genet. 1999, 37, 157-165
5. Greatbanks, S. P.; Gready, J. E.; Limaye, A. C.; Rendell, A. P. Comparison of Enzyme Polarization of Ligands and Charge-Transfer Effects for Dihydrofolate Reductase Using Point-Charge Embedded ab initio Quantum Mechanical and Linear-Scaling Semiempirical Quantum Mechanical Methods J. Comput. Chem. 2000, 21, 788-811
6. Broadus, K. M.; Kass, S. R. The Electron as a Protecting Group. 2. Generation of Benzocyclobutadiene Radical Anion in the Gas Phase and an Experimental Determination of the Heat of Formation of Benzocyclobutadiene J. Am. Chem. Soc. 2000, 122, 10697-10703
7. Broadus, K. M.; Kass, S. R. The Electron as a Protecting Group. 3. Generation of Acenaphthyne Radical Anion and the Determination of the Heat of Formation of a Strained Cycloalkyne J. Am. Chem. Soc. 2001, 123, 4189-4196
8. Murad, E. The Shuttle Glow Phenomenon Annu. Rev. Phys. Chem. 1998, 49, 73-98
9. Wang, R. L.; Moshurchak, L. M.; Lamanna, W. M.; Bulinski, M.; Dahn, J. R. A Combined Computational/Experimental Study on Tertbutyl- and Methoxy-Substituted Benzene Derivatives as Redox Shuttles for Lithium-Ion Cells J. Electrochem. Soc. 2008, 155, A66-A73
10. Wallington, T. J.; Egsgaard, H.; Nielsen, O. J.; Platz, J.; Sehested, J.; Stein, T. UV-Visible Spectrum of the Phenyl Radical and Kinetics of Its Reaction with NO in the Gas Phase Chem. Phys. Lett. 1998, 290, 363-370
11. Hansch, C.; Fujita, T. p-σ-π Analysis. A Method for the Correlation of Biological Activity and Chemical Structure J. Am. Chem. Soc. 1964, 86, 1616-1626
12. Reynolds, C. A.; King, P. M.; Richards, W. G. Computed Redox Potentials and the Design of Bioreductive Agents Nature 1988, 334, 80-82
13. Reynolds, C. A. Theoretical Electrode Potentials and Conformational Energies of Benzoquinones and Naphthoquinones in Aqueous Solution J. Am. Chem. Soc. 1990, 112, 7545-7551
14. Peover, M. E. Electrochemistry of Aromatic Hydrocarbons and Related Substances. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker, Inc.: New York, 1967; Vol. 2, pp 1-51.
15. Rienstra-Kiracofe, J. C.; Tschumper, G. S.; Schaefer, H. F., III; Nandi, S.; Ellison, G. B. Atomic and Molecular Electron Affinities: Photoelectron Experiments and Theoretical Computations Chem. Rev. 2002, 102, 231-282
16. 1/2 Values by Medium Effects J. Am. Chem. Soc. 2006, 128, 3980-3989
17. Lehmann, M. W.; Evans, D. H. Toward Infinite-Dilution Voltammetry J. Phys. Chem. B 1998, 102, 9928-9933
18. Davis, A. P.; Fry, A. J. Experimental and Computed Absolute Redox Potentials of Polycyclic Aromatic Hydrocarbons are Highly Linearly Correlated over a Wide Range of Structures and Potentials J. Phys. Chem. A 2010, 114, 12299-12304
19. Hicks, L. D.; Fry, A. J.; Kurzweil, V. C. Ab Initio Computation of Electron Affinities of Substituted Benzalacetophenones (Chalcones): a New Approach to Substituent Effects in Organic Electrochemistry Electrochim. Acta 2004, 50, 1039-1047
20. Fry, A. J. A computational Study of Solution Effects on the Disproportionation of Electrochemically Generated Polycyclic Aromatic Hydrocarbon Radical Anions. Thermodynamics and Structure Tetrahedron 2006, 62, 6558-6565
21. Speelman, A. L.; Gillmore, J. G. Efficient Computational Methods for Accurately Predicting Reduction Potentials of Organic Molecules J. Phys. Chem. A 2008, 112, 5684-5690
22. Lynch, E. J.; Speelman, A. L.; Curry, B. A.; Murillo, C. S.; Gillmore, J. G. Expanding and Testing a Computational Method for Predicting the Ground State Reduction Potentials of Organic Molecules on the Basis of Empirical Correlation to Experiment J. Org. Chem. 2012, 77, 6423-6430
23. Méndez-Hernández, D. D.; Tarakeshwar, P.; Gust, D.; Moore, T. A.; Moore, A. L.; Mujica, V. Simple and Accurate Correlation of Experimental Redox Potentials and DFT-Calculated HOMO/LUMO Energies of Polycyclic Aromatic Hydrocarbons J. Mol. Model. 2012, 10.1007/s00894-012-1694-7
24. Fry, A. J. Computational Studies of Ion Pairing. 8. Ion Pairing of Tetraalkylammonium Ions to Nitrosobenzene and Benzaldehyde Redox Species. A General Binding Motif for the Interaction of Tetraalkylammonium Ions with Benzenoid Species J. Org. Chem. 2013, 78, 5476-5481
25. Fry, A. J. Computational Studies of Ion Pairing. 7. Ion-Pairing and Association Effects between Tetraalkylammonium Ions and Nitrobenzene Redox Species. Ion Pairing to Neutral Substances J. Org. Chem. 2013, 78, 2111-2117
26. Fry, A. J. The Effect of Tetramethylammonium Ion on the Voltammetric Behavior of Polycyclic Aromatic Hydrocarbons: Computations Explain a Long-standing Anomaly Phys. Chem. Chem. Phys. 2010, 12, 14775-14781
27. Fry, A. J.; Steffen, L. K. On the Nature of Tetraalkylammonium Ions in Common Electrochemical Solvents: General and Specific Solvation-Quantitative Aspects J. Electroanal. Chem. 2010, 638, 218-224
28. Wu, X.; Davis, A. P.; Lambert, P. C.; Steffen, L. K.; Toy, O.; Fry, A. J. Substituent Effects on the Redox Properties and Structure of Substituted Triphenylamines. An Experimental and Computational Study Tetrahedron 2009, 65, 2408-2414
29. Nayak, P. K.; Periasamy, N. Calculation of Electron Affinity, Ionization Potential, Transport Gap, Optical Band Gap and Exciton Binding Energy of Organic Solids Using 'Solvation' Model and DFT Org. Electron. 2009, 10, 1396-1400
30. Roy, L. E.; Jakubikova, E.; Guthrie, M. G.; Batista, E. R. Calculation of One-Electron Redox Potentials Revisited. Is It Possible to Calculate Accurate Potentials with Density Functional Methods? J. Phys. Chem. A 2009, 113, 6745-6750
31. Namazian, M.; Coote, M. L. Accurate Calculation of Absolute One-Electron Redox Potentials of Some para-Quinone Derivatives in Acetonitrile J. Phys. Chem. A 2007, 111, 7227-7232
32. Li, X.-L.; Fu, Y. Theoretical Study of Reduction Potentials of Substituted Flavins J. Mol. Struct.: THEOCHEM 2008, 856, 112-118
33. Gritzner, G.; KuÌŠta, J. Recommendations on Reporting Electrode Potentials in Nonaqueous Solvents Pure Appl. Chem. 1982, 54, 1527-1532
34. Gritzner, G.; KuÌŠta, J. Recommendations on Reporting Electrode Potentials in Nonaqueous Solvents: IUPC Commission on Electrochemistry Electrochim. Acta 1984, 29, 869-873
35. Electronic Aspects of Ionic Liquids, 2 nd ed.; Ohno, H., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2011.
36. Hapiot, P.; Lagrost, C. Electrochemical Reactivity in Room-Temperature Ionic Liquids Chem. Rev. 2008, 108, 2238-2264 and references therein
37. Barrosse-Antle, L. E.; Bond, A. M.; Compton, R. G.; O'Mahony, A. M.; Rogers, E. I.; Silvester, D. S. Voltammetry in Room Temperature Ionic Liquids: Comparisons and Contrasts with Conventional Electrochemical Solvents Chem. Asian J. 2010, 5, 202-230 and references therein
38. Paîrvulescu, V. I.; Hardacre, C. Catalysis in Ionic Liquids Chem. Rev. 2007, 107, 2615-2665
39. Belding, S. R.; Rees, N. V.; Aldous, L.; Hardacre, C.; Compton, R. G. Behavior of the Heterogeneous Electron-Transfer Rate Constants of Arenes and Substituted Anthracenes in Room-Temperature Ionic Liquids J. Phys. Chem. C 2008, 112, 1650-1657
40. Ji, X.; Silvester, D. S.; Aldous, L.; Hardacre, C.; Compton, R. G. Mechanistic Studies of the Electro-Oxidation Pathway of Ammonia in Several Room-Temperature Ionic Liquids J. Phys. Chem. C 2007, 111, 9562-9572
41. Allen, G. D.; Buzzeo, M. C.; Villagrán, C.; Hardacre, C.; Compton, R. G. A Mechanistic Study of the Electro-Oxidation of Bromide in Acetonitrile and the Room Temperature Ionic Liquid, 1-Butyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)imide at Platinum Electrodes J. Electroanal. Chem. 2005, 575, 311-320
42. Aldous, L.; Silvester, D. S.; Villagrán, C.; Pitner, W. R.; Compton, R. G.; Lagunas, M. C.; Hardacre, C. Electrochemical Studies of Gold and Chloride in Ionic Liquids New J. Chem. 2006, 30, 1576-1583
43. Lagrost, C.; Carrié, D.; Vaultier, M.; Hapiot, P. Reactivities of Some Electrogenerated Organic Cation Radicals in Room-Temperature Ionic Liquids: Toward an Alternative to Volatile Organic Solvents? J. Phys. Chem. A 2003, 107, 745-752
44. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Reactivity of Ionic Liquids Tetrahedron 2007, 63, 2363-2389
45. Sun, H.; Yu, L.; Jin, X.; Hu, X.; Wang, D.; Chen, G. Z. Unusual Anodic Behaviour of Chloride Ion in 1-Butyl-3-methylimidazolium Hexafluorophosphate Electrochem. Commun. 2005, 7, 685-691
46. Zhang, J.; Bond, A. M. Conditions Required to Achieve the Apparent Equivalence of Adhered Solid- and Solution-Phase Voltammetry for Ferrocene and Other Redox-Active Solids in Ionic Liquids Anal. Chem. 2003, 75, 2694-2702
47. Zhao, S.; Lu, J.; Bond, A. M.; Zhang, J. Voltammetric Studies in "Wet" 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethylsulfonyl)imide Ionic Liquid Using Electrodes with Adhered Microparticles Electrochem. Commun. 2012, 16, 14-18
48. Turner, M. B.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. Production of Bioactive Cellulose Films Reconstituted from Ionic Liquids Biomacromolecules 2004, 5, 1379-1384
49. Turner, M. B.; Spear, S. K.; Holbrey, J. D.; Daly, D. T.; Rogers, R. D. Ionic Liquid-Reconstituted Cellulose Composites as Solid Support Matrices for Biocatalyst Immobilization Biomacromolecules 2005, 6, 2497-2502
50. Lozano, P.; de Diego, T.; Carrié, D.; Vaultier, M.; Iborra, J. L. Continuous Green Biocatalytic Processes Using Ionic Liquids and Supercritical Carbon Dioxide Chem. Commun. 2002, 692-693
51. MacFarlane, D. R.; Forsyth, M.; Howlett, P. C.; Pringle, J. M.; Sun, J.; Annat, G.; Neil, W.; Izgorodina, E. I. Ionic Liquids in Electrochemical Devices and Processes: Managing Interfacial Electrochemistry Acc. Chem. Res. 2007, 40, 1165-1173
52. Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Metal-Free Organic Dyes for Dye-Sensitized Solar Cells: From Structure: Property Relationships to Design Rules Angew. Chem., Int. Ed. 2009, 48, 2474-2499
53. Wei, D.; Ng, T. W. Application of Novel Room Temperature Ionic Liquids in Flexible Supercapacitors Electrochem. Commun. 2009, 11, 1996-1999
54. Fernicola, A.; Navarra, M. A.; Panero, S. Aprotic Ionic Liquids as Electrolyte Components in Protonic Membranes J. Appl. Electrochem. 2008, 38, 993-996
55. Orita, A.; Kamijima, K.; Yoshida, M.; Dokko, K.; Watanabe, M. Favorable Combination of Positive and Negative Electrode Materials with Glyme-Li Salt Complex Electrolytes in Lithium Ion Batteries J. Power Sources 2011, 196, 3874-3880
56. Barhdadi, R.; Courtinard, C.; Nédélec, J. Y.; Troupel, M. Room-Temperature Ionic Liquids as New Solvents for Organic Electrosynthesis. The First Examples of Direct or Nickel-Catalysed Electroreductive Coupling Involving Organic Halides Chem. Commun. 2003, 1434-1435
57. Doherty, A. P.; Brooks, C. A. Electrosynthesis in Room-Temperature Ionic Liquids: Benzaldehyde Reduction Electrochim. Acta 2004, 49, 3821-3826
58. Torriero, A. A. J.; Howlett, P. C. Ionic Liquid Effects on the Redox Potential of Ferrocene Electrochem. Commun. 2012, 16, 84-87
59. Bizzarri, C.; Conte, V.; Floris, B.; Galloni, P. Solvent Effects of Ionic Liquids: Investigation of Ferrocenes as Electrochemical Probes J. Phys. Org. Chem. 2011, 24, 327-334
60. Nagy, L.; Gyetvai, G.; Kollár, L.; Nagy, G. Electrochemical Behavior of Ferrocene in Ionic Liquid Media J. Biochem. Biophys. Methods 2006, 69, 121-132
61. Cruz, H.; Gallardo, I.; Guirado, G. Understanding Specific Effects on the Standard Potential Shifts of Electrogenerated Species in 1-Butyl-3- methylimidazolium Ionic Liquids Electrochim. Acta 2008, 53, 5968-5976
62. Fry, A. J. Strong Ion-Pairing Effects in a Room Temperature Ionic Liquid J. Electroanal. Chem. 2003, 546, 35-39
63. Nikitina, V. A.; Nazmutdinov, R. R.; Tsirlina, G. A. Quinones Electrochemistry in Room-Temperature Ionic Liquids J. Phys. Chem. B 2011, 115, 668-677
64. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Molecular States of Water in Room Temperature Ionic Liquids Phys. Chem. Chem. Phys. 2001, 3, 5192-5200
65. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room Temperature Ionic Liquids as Novel Media for 'Clean' Liquid-Liquid Extraction Chem. Commun. 1998, 1765-1766
66. Uno, B.; Okumura, N.; Goto, M.; Kano, K. n-σ Charge-Transfer Interaction and Molecular and Electronic Structural Properties in the Hydrogen-Bonding Systems Consisting of p -Quinone Dianions and Methyl Alcohol J. Org. Chem. 2000, 65, 1448-1455
67. Uno, B.; Kano, K.; Konse, T.; Kubota, T.; Matsuzaki, S.; Kuboyama, A. Origin of the Negative Shift of Half-Wave Reduction Potentials of Aromatic Polynuclear π-Quinones with Increasing Conjugation Chem. Pharm. Bull. 1985, 33, 5155-5166
68. Kubota, T.; Kano, K.; Uno, B.; Konse, T. Energetics of the Sequential Electroreduction and Electrooxidation Steps of Benzenoid Hydrocarbons Bull. Chem. Soc. Jpn. 1987, 60, 3865-3877
69. Uno, B.; Okumura, N.; Seto, K. Bistable Charge-Transfer Complex Formation of Redox-Active Organic Molecules Based on Intermolecular HOMO-LUMO Interaction Controlled by the Redox Reactions J. Phys. Chem. A 2000, 104, 3064-3072
70. + Reference Electrode for Use in Room Temperature Ionic Liquids Electrochem. Commun. 2006, 8, 1405-1411
71. Kano, K.; Mori, K.; Konse, T.; Uno, B.; Kubota, T. In-Situ Electron Spin Resonance and Voltammetric Studies Using an Internal-Flow-Type Electrolysis Cell Anal. Sci. 1989, 5, 651-656
72. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
73. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. Solvent Effects. 5. Influence of Cavity Shape, Truncation of Electrostatics, and Electron Correlation on ab Initio Reaction Field Calculations J. Phys. Chem. 1996, 100, 16098-16104
74. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3093
75. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Ab Initio Study of Solvated Molecules: a New Implementation of the Polarizable Continuum Model Chem. Phys. Lett. 1996, 255, 327-335
76. Politzer, P.; Abu-Awwad, F. A Comparative Analysis of Hartree-Fock and Kohn-Sham Orbital Energies Theor. Chem. Acc. 1998, 99, 83-87
77. Stowasser, R.; Hoffmann, R. What Do the Kohn-Sham Orbitals and Eigenvalues Mean? J. Am. Chem. Soc. 1999, 121, 3414-3420
78. Zhang, G.; Musgrave, C. B. Comparison of DFT Methods for Molecular Orbital Eigenvalue Calculations J. Phys. Chem. A 2007, 111, 1554-1561
79. Kar, R.; Song, J.-W.; Hirao, K. Long-Range Corrected Functionals Satisfy Koopmans' Theorem: Calculation of Correlation and Relaxation Energies J. Comput. Chem. 2013, 34, 958-964
80. Tsuneda, T.; Song, J. W.; Suzuki, S.; Hirao, K. On Koopmans' Theorem in Density Functional Theory J. Chem. Phys. 2010, 133, No. 174101.
81. Belding, S. R.; Limon-Petersen, J. G.; Dickinson, E. J. F.; Compton, R. G. Cyclic Voltammetry in the Absence of Excess Supporting Electrolyte Offers Extra Kinetic and Mechanistic Insights: Comproportionation of Anthraquinone and the Anthraquinone Dianion in Acetonitrile Angew. Chem., Int. Ed. 2010, 49, 9242-9245
82. Chambers, J. Q. The Chemistry of Quinonoid Compounds; Wiley: New York, 1988; Vol. 2.
83. Parker, V. D. The Study of Reactive Intermediates by Electrochemical Methods Adv. Phys. Org. Chem. 1983, 19, 131-222
84. Jensen, B. S.; Parker, V. D. Reactions of Aromatic Anion Radicals and Dianions. II. Reversible Reduction of Anion Radicals to Dianions J. Am. Chem. Soc. 1975, 97, 5211-5217
85. Parker, V. D. Energetics of Electrode Reactions. II. The Relationship Between Redox Potentials, Ionization Potentials, Electron Affinities, and Solvation Energies of Aromatic Hydrocarbons J. Am. Chem. Soc. 1976, 98, 98-103
86. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-Aqueous Systems; Marcel Dekker: New York, 1970.
87. Wu, J.; Stark, J. P. W. Measurement of Low Frequency Relative Permittivity of Room Temperature Molten Salts by Triangular Waveform Voltage Meas. Sci. Technol. 2006, 17, 781-788
88. Wakai, C.; Oleinikova, A.; Ott, M.; Weingärtner, H. How Polar Are Ionic Liquids? Determination of the Static Dielectric Constant of an Imidazolium-Based Ionic Liquid by Microwave Dielectric Spectroscopy J. Phys. Chem. B 2005, 109, 17028-17030
89. Huang, M.; Jiang, Y.; Sasisanker, P.; Driver, G. W.; Weingärtner, H. Static Relative Dielectric Permittivities of Ionic Liquids at 25 C J. Chem. Eng. Data 2011, 56, 1494-1499
90. Izgorodina, E. I.; Forsyth, M.; MacFarlane, D. R. On the Components of the Dielectric Constants of Ionic Liquids: Ionic Polarization? Phys. Chem. Chem. Phys. 2009, 11, 2452-2458
91. Weingärtner, H. The Static Dielectric Constant of Ionic Liquids Z. Phys. Chem. 2006, 220, 1395-1405
92. Stoppa, A.; Hunger, J.; Buchner, R.; Hefter, G.; Thoman, A.; Helm, H. Interactions and Dynamics in Ionic Liquids J. Phys. Chem. B 2008, 112, 4854-4858
93. Weingärtner, H.; Sasisanker, P.; Daguenet, C.; Dyson, P. J.; Krossing, I.; Slattery, J. M.; Schubert, T. The Dielectric Response of Room-Temperature Ionic Liquids: Effect of Cation Variation J. Phys. Chem. B 2007, 111, 4775-4780
94. Kosmulski, M.; Marczewska-Boczkowska, K.; Zukowski, P.; Subocz, J.; Saneluta, C. Permittivities of 1-Alkyl-3-methylimidazolium Tetrafluoroborates and Hexafluorophosphates Croat. Chem. Acta 2007, 80, 461-466
95. Onsager, L. Electric Moments of Molecules in Liquids J. Am. Chem. Soc. 1936, 58, 1486-1493
96. Zumman, P. Substituent Effects in Organic Polarography; Plenum: New York, 1967.
97. Leventis, N.; Rawaswdeh, A. M.; Zhang, G.; Elder, I. A.; Sotiriou-Leventis, C. Tuning the Redox Chemistry of 4-Benzoyl-N-methylpyridinium Cations through Para Substitution. Hammett Linear Free Energy Relationships and the Relative Aptitude of the Two-Electron Reduced Forms for H-Bonding J. Org. Chem. 2002, 67, 7501-7510
98. Parsons, R. The Single Electrode Potential: Its Significance and Caluculation. In Standard Potentials in Aqueous Solution; Bard, A. J.; Parsons, R.; Jordan, J., Eds.; Marcel Dekker: New York, 1985; Chapter 2.
99. Trasatti, S. The Absolute Electrode Potential: an Explanatory Note Pure Appl. Chem. 1986, 58, 955-966
100. Ryan, M. F.; Richardson, D. E.; Lichtenberger, D. L.; Gruhn, N. E. Gas-Phase Ionization Energetics, Electron-Transfer Kinetics, and Ion Solvation Thermochemistry of Decamethylmetallocenes, Chromocene, and Cobaltocene Organometallics 1994, 13, 1190-1199
101. Nelsen, S. F.; Rumack, D. T.; Meot-Ner, M. Gas-Phase Electron-Transfer Equilibrium Studies on Tetraalkylhydrazines: Geometry Effects on Ionization Thermochemistry, Relaxation Energies, and Ion Solvation Energies J. Am. Chem. Soc. 1988, 110, 7945-7952
102. Shalev, H.; Evans, D. H. Solvation of Anion Radicals: Gas-Phase versus Solution J. Am. Chem. Soc. 1989, 111, 2667-2674
103. Heinis, T.; Chowdhury, S.; Scott, S. L.; Kebarle, P. Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements J. Am. Chem. Soc. 1988, 110, 400-407
104. Uno, B.; Matsuhisa, Y.; Kano, K.; Kubota, T. Relation between the First and the Second Nonaqueous Reduction Potentials of Substituted Stilbenes Chem. Pharm. Bull. 1984, 32, 1-10
105. Cape, J. L.; Bowman, M. K.; Kramer, D. M. Computation of the Redox and Protonation Properties of Quinones: Towards the Prediction of Redox Cycling Natural Products Phytochemistry 2006, 67, 1781-1788