Quantum-chemical predictions of absolute standard redox potentials of diverse organic molecules and free radicals in acetonitrile

Journal of the American Chemical Society

Volumn 127, Issue 19, 2005, Pages 7227-7234

  Fu, Yao ^a   Liu, Lei ^a   Yu, Hai Zhu ^a   Wang, Yi Min ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENCHMARKING; CHARGE TRANSFER; CONTINUUM MECHANICS; ELECTROCHEMISTRY; FREE RADICALS; IONIZATION; ORGANIC COMPOUNDS; REDOX REACTIONS;

ADIABATIC IONIZATION POTENTIALS; COMPUTATIONAL ELECTROCHEMISTRY; QUANTUM CHEMISTRY; REDOX POTENTIALS;

QUANTUM THEORY;

ACETONITRILE; FREE RADICAL;

ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; PREDICTION; QUANTUM CHEMISTRY; SOLVATION;

EID: 18744394619     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0421856     Document Type: Article

References (68)

1. The standard redox potential refers to standard conditions (i.e., all reactants are 1.0 M or 1 atm pressure, 298 K). Also, in the present study we only considered the single-electron transfer redox potentials. Furthermore, people have defined both the oxidation potentials and reduction potentials by using different orders of half reactions. In the present study, we only considered the redox potential that corresponded to the oxidation of a species. For the reduction of a species, one just needs to consider the oxidation of the corresponding reduced form.
2. (a) Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; Wiley; New York, 2001.
3. (b) Hamann, C. H.; Hamnett, A.; Vielstich, W. Electrochemistry; Wiley-VCH; New York, 1998.
4. (c) Photochemistry and Radiation Chemistry: Complementary Methods for the Study of Electron Transfer; Wishart, J. F., Nocera, D. G., Eds.; Advances in Chemistry Series 254; American Chemical Society: Washington, DC, 1998.
5. Rychnovsky, S. D.; Vaidyanathan, R.; Beauchamp, T.; Lin, R.; Farmer, P. J. J. Org. Chem. 1999, 64, 6745.
6. Charles-Nicolas, O.; Lacroix, J. C.; Lacaze, P. C. J. Chim. Phys. 1998, 95, 1457.
7. Raymond, K. S.; Grafton, A. K.; Wheeler, R. A. J. Phys. Chem. B 1997, 101, 623.
8. (a) Baik, M.-H.; Silverman, J. S.; Yang, I. V.; Ropp, P. A.; Szalai, V. A.; Yang, W. T.; Thorp, H. H. J. Phys. Chem. B 2001, 105, 6437.
9. (b) Baik, M.-H.; Friesner, R. A. J. Phys. Chem. A 2002, 106, 7407.
10. Uudsemaa, M.; Tamm, T. J. Phys. Chem. A 2003, 107, 9997.
11. (a) Namazian, M.; Norouzi, P.; Ranjbar, R. J. Mol Struct. (THEOCHEM) 2003, 625, 235.
12. (b) Namazian, M. J. Mol. Struct. (THEOCHEM) 2003, 664-665, 273.
13. (a) Winget, P.; Weber, E. J.; Cramer, C. J.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2000, 2, 1231.
14. (b) Patterson, E. V.; Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 2001, 123, 2025.
15. (c) Arnold, W. A.; Winget, P.; Cramer, C. J. Environ. Sci. Technol. 2002, 36, 3536.
16. Fu, Y.; Liu, L.; Li, R.-Q.; Liu, R.; Guo, Q.-X. J. Am. Chem. Soc. 2004, 126, 814.
17. Due to the limitation of the computer resources, we only selected the compounds that contain no more than 12 non-hydrogen atoms. Moreover, we only selected the redox potentials corresponding to the one-electron transfer process.
18. Rao, P. S.; Hayon, E. J. Am. Chem. Soc. 1974, 96, 1287.
19. Papaconstantinou, E. Anal. Chem. 1975, 47, 1592.
20. (a) Wayner, D. D. M.; Griller, D. J. Am. Chem. Soc. 1985, 107, 7764.
21. (b) Wayner, D. D. M.; Dannenberg, J. J.; Griller, D. Chem. Phys. Lett. 1986, 131, 189.
22. (c) Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132.
23. (d) Sim, B. A.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1989, 111, 754.
24. (e) Sim, B. A.; Milne, P. H.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1990, 112, 6635.
25. (f) Wayner, D. D. M.; Sim, B. A.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 4853.
26. (g) Wayner, D. D. M.; Houmam, A. Acta Chem. Scand. 1998, 52, 377.
27. (a) Occhialini, D.; Federsen, S. U.; Lund, H. Acta Chem. Scand. 1990, 44, 715.
28. (b) Occhialini, D.; Kristensen, J. S.; Daasbjerg, K.; Lund, H. Acta Chem. Scand. 1992, 46, 474.
29. (c) Occhialini, D.; Daasbjerg, K.; Lund, H. Acta Chem. Scand. 1993, 47, 1100.
30. Abe, T. Bull. Chem. Soc. Jpn. 1994, 67, 699.
31. Hapiot, P.; Konovalov, V. V.; Saveant, J.-M. J. Am. Chem. Soc. 1995, 117, 1428.
32. (a) Jonsson, M.; Wayner, D. D. M.; Lusztyk, J. J. Phys. Chem. 1996, 100, 17539.
33. (b) Jonsson, M.; Kraatz, H. B. J. Chem. Soc., Perkin Trans. 2 1997, 2673.
34. (a) Larsen, A. G.; Holm, A. H.; Roberson, M.; Daasbjerg, K. J. Am. Chem. Soc. 2001, 123, 1723.
35. (b) Lund, T.; Wayner, D. D. M.; Jonsson, M.; Larsen, A. G.; Daasbjerg, K. J. Am. Chem. Soc. 2001, 123, 12590.
36. Cardinale, A.; Isse, A. A.; Gennaro, A. Electrochem. Commun. 2002, 4, 767.
37. Andrieux, C. P.; Pinson, J. J. Am. Chem. Soc. 2003, 125, 14801.
38. Grampp, G.; Landgraf, S.; Muresanu, C. Electrochim. Acta 2004, 49, 537.
39. Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 452, 145 and references therein.
40. Thomas, F.; Kollman, P. A. J. Phys. Chem. 1996, 100, 2950.
41. (a) Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
42. (b) Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 1998, 102, 870.
43. (c) Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 4690.
44. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
45. (a) Cramer, C. J.; Truhlar, D. G. Rev. Comput. Chem. 1995, 6, 1.
46. (b) Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
47. Pliego, J. R., Jr.; Riveros, J. M. Chem. Phys. Lett. 2002, 355, 543.
48. There are five solvation free energy data for acetonitrile that range from -3.57 to -5.33 kcal/mol (see: Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 1998, 102, 3257). It is not sensible to optimize the f value or to evaluate the solvation model using these five similar data.
49. (a) Stanczyk-Dunaj, M.; Galezowski, W.; Jarczewski, A. Can. J. Chem. 2002, 80, 1259.
50. (b) Chantooni, M. K., Jr.; Kolthoff, I. M. J. Phys. Chem. 1976, 80, 1306.
51. (c) Leito, I.; Kaljurand, I.; Koppel, I. A.; Yagupolskii, L. M.; Vlasov, V. M. J. Org. Chem. 1998, 63, 7863.
52. (d) Kolthoff, I. M.; Chantooni, M. K., Jr.; Bhowmik, S. J. Am. Chem. Soc. 1968, 90, 23.
53. (e) Chantooni, M. C., Jr.; Kolthoff, I. M. J. Phys. Chem. 1975, 79, 1176.
54. (f) Ludwig, M.; Pytela, O.; Vecera, M. Collect. Czech. Chem. Commun. 1984, 49, 2593.
55. Bondi, A. J. Phys. Chem. 1964, 68, 441.
56. Kolthoff, I. M.; Chantooni, M. K. J. Phys. Chem. 1968, 72, 2270.
57. In calculating the entropy change, one needs to include an extra term (-RT In 4 = -0.04 eV) in addition to the standard thermal entropy terms. This term corresponds to the entropic contribution from the electronic spin degeneracy.
58. Trasatti, S. Pure Appl. Chem. 1986, 58, 955.
59. + (0.1 M) versus NHE = +0.57 V.
60. (a) Fleischmann, M.; Pletcher, D. Tetrahedron Lett. 1968, 60, 6255.
61. (b) Clark, D. B.; Fleischmann, M.; Pletcher, D. J. Electroanal. Chem. Interfacial Electrochem. 1973, 42, 133.
62. Loveland. J. W.; Dimeler, G. R. Anal. Chem. 1961, 33, 1196.
63. Miller, L. L.; Nordblom, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916.
64. Recent examples: (a) Dhiman, A.; Becker, J. Y.; Minge, O.; Schmidbaur, H.; Muller, T. Organometallics 2004, 23, 1636.
65. (b) Ue, M.; Murakami, A.; Nakamura, S. J. Am. Chem. Soc. 2002, 149, 1572.
66. Only the carbon-centered free radicals are considered in the present study.
67. Frisch, M. J. et al. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
68. Frisch, M. J. et al. Gaussian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.