Speciation of 1-alkyl-4-cyanopyridinium iodide

Journal of Physical Chemistry A

Volumn 101, Issue 9, 1997, Pages 1774-1781

  Binder, David A ^a,b   Kreevoy, Maurice M ^a  

^a University of Minnesota   (United States)

^b Lever Brothers Co   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ELECTRIC CONDUCTIVITY MEASUREMENT; MOLECULAR STRUCTURE;

CONTACT ION PAIRS; SOLVENT-SEPARATED ION PAIRS;

CHARGE TRANSFER;

EID: 0031071082     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp963886v     Document Type: Article

References (76)

1. Bjerrum, N. K. Dan. Vidensk. Selsk. 1926, 7, No. 9.
2. Winstein, J.; Robinson, G. C. J. Am. Chem. Soc. 1958, 80, 169.
3. Sadek, H.; Fuoss, R. M. J. Am. Chem. Soc. 1954, 76, 5905.
4. Bentley, T. W.; Schleyer, P. V. R. Adv. Phys. Org. Chem. 1977, 14, 1.
5. Raber, D. J.; Harris, J. M.; Schleyer, P. V. R. Ions and Ion Pairs in Organic Reactions; Wiley: New York, 1974; Vol. 2, Chapter 3.
6. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
7. Richard, J. P. Advances in Carbocation Chemistry; JAI Press, Inc.: Greenwich, CT, 1989; Vol. 1.
8. Bagchi, S.; Pal, M. J. Chem. Soc., Perkin Trans. 1 1985, 81, 2323.
9. Smid, J. Ions and Ion pairs in Organic Reactions; Wiley: New York, 1972; Vol. 1, Chapter 2.
10. Fuoss, R. M.; Accascina, F. Electrolytic Conductance; Interscience: New York, 1959.
11. Grunwald, E.; Kohinoor Begum, M. J. Am. Chem. Soc. 1990, 112, 5104.
12. Nicolas, M.; Reich, R. J. Phys. Chem. 1981, 85, 2843.
13. O'Brian, D. H.; Russell, C. R.; Hart, A. J. J. Am. Chem. Soc. 1979, 101, 633.
14. Hogen-Esch, T. E. J. Am. Chem. Soc. 1966, 88, 307.
15. Szwarc, M. Acc. Chem. Res 1969, 2, 82.
16. Grunwald, E. Anal. Chem. 1954, 26, 1696.
17. Hemmes, P.; Costanzo, J. N.; Jordan, F. J. Phys. Chem. 1978, 82, 387.
18. Smid, J. J. Am. Chem. Soc. 1966, 88, 307.
19. Peters, K. S.; Simon, J. D. J. Am. Chem. Soc. 1982, 104, 6542.
20. Hilininski, E. F.; Masnovi, J. M.; Kochi, J. K.; Rentzepic, P. M. J. Am. Chem. Soc. 1984, 106, 8071.
21. Ciccotti, G.; Ferrario, M.; Hynes, J. T.; Kapral, R. J. Chim. Phys. 1988, 85, 925.
22. Ciccotti, G.; Ferrario, M.; Hynes, J. T.; Kapral, R. Chem. Phys. 1989, 129, 241.
23. Ciccotti, G.; Ferrario, M.; Hynes, J. T.; Kapral, R. J. Chem. Phys. 1990, 93, 7137.
24. Ciccotti, G.; Ferrario, M.; Hynes, J. T.; Kapral, R. J. Chem. Phys. 1990, 93, 7137.
25. Madhusoodanan, M.; Tembe, B. L. J. Phys. Chem. 1994, 98, 7090.
26. Reichardt, C. Solvents and Solvent Effects in Organic Chemisty, 2nd ed.; VCH Publishers: New York, 1994.
27. Horng, M. L.; Gardecki, J. A.; Papazan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311, and refs 98 and 99 cited within.
28. Bockman, T. M.; Chang, H. R.; Drickamer, H. G.; Kochi, J. J. Phys. Chem. 1990, 94, 8483.
29. Bockman, T. M.; Kochi, J. J. Am. Chem. Soc. 1989, 111, 4669.
30. Arnold, B. R.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1996, 118, 5482.
31. Peters, K. S.; Li, B. J. Phys. Chem. 1994, 98, 401.
32. Binder, D. A.; Mead, C. A.; Kreevoy, M. M. Croat. Chem. Acta 1992, 65, 763.
33. Morgan, C. R.; Ketley, A. D. J. Rad. Curing 1980, 7, 10.
34. Binder, D. A. Ionic Interactions in Solvents of Weak and Intermediate Polarity. Ph.D. Thesis, University of Minnesota, 1994.
35. Binder, D. A.; Kreevoy, M. M. J. Phys. Chem. 1994, 98, 10008.
36. Siano, D. B.; Metzler, D. E. J. Chem. Phys. 1969, 51, 1856.
37. Reefer, R. M.; Andrews, L. J. J. Am. Chem. Soc. 1952, 74, 69.
38. Ross, S. D.; Bassin, M.; Finkelstein, M.; Leach, W. A. J. Am. Chem. Soc. 1954, 76, 69.
39. Kosower, E. M.; Burbach, J. C. J. Am. Chem. Soc. 1956, 78, 5838.
40. Lee, W. H.; Wheaton, R. J. J. Chem. Soc., Faraday Trans. 2 1978, 74, 743.
41. Lee, W. H.; Wheaton, R. J. J. Chem. Soc., Faraday Trans. 2 1978, 74, 1456.
42. Lee, W. H.; Wheaton, R. J. J. Chem. Soc., Faraday Trans. 2 1979, 75, 1128.
43. Gilkerson, W. R.; Kendrick, K. L. J. Phys. Chem. 1984, 88, 5352.
44. Kendrick, K. L.; Gilkerson, W. R. J. Solut. Chem. 1986, 15, 253.
45. Davis, K. M. C. Molecular Association; Academic Press: New York, 1975; Vol. 1, Chapter 3.
46. Jaffé, H. H.; Orchin, M. Theory and Applications of Ultraviolet Spectroscopy; John Wiley and Sons: New York, 1962.
47. Mulliken, R. S. J. Chem. Phys. 1939, 7, 14.
48. Demtröder, W. Laser Spectroscopy: Basic Concepts and Instrumentation; Springer-Verlag: New York, 1982.
49. Ritchie, C. D. Physical Organic Chemistry: The Fundamental Concepts, 2nd ed.; Marcel Dekker, Inc: New York, 1990.
50. 17 and the coefficients were determined by fitting the data from Table 5.
51. Kjaer, A. M.; Ulstrup, J. J. Am. Chem. Soc. 1987, 109, 1934.
52. Ooshika, Y. J. Phys. Soc. Jpn. 1954, 9, 594.
53. Lippert, E. Z. Naturforsch. 1955, A10, 541.
54. McRae, E. G. J. Phys. Chem. 1957, 61, 562.
55. Mataga, N.; Kubota, T. In Molecular Interactions & Electronic Spectra; Mercel Dekker: New York, 1970; p 371.
56. Amos, A. T.; Burrows, B. Adv. Quantum Chem. 1973, 7, 289.
57. Liptay, W. In Excited States; Lim, E. C., Ed.; Academic Press: New York, 1974; Vol. 1, p 129.
58. Horng, M. L.; Gardecki, J. A.; Papazan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311.
59. Mackay, R. A.; Poziomek, E. J. J. Am. Chem. Soc. 1970, 92, 2432.
60. Acevedo, V. H.; deMoran, J. A.; Sales, L. A. Can. J. Chem. 1983, 61, 267.
61. Matheson, R. A. J. Phys. Chem. 1965, 69, 1537.
62. Milne, J. B.; Parker, T. J. J. Solut. Chem. 1981, 10, 479.
63. Davies, W. G.; Otter, R. J.; Prue, J. E. Discuss. Faraday Soc 1957, 24, 103.
64. Feng-Chun, H.; Gilkerson, W. R. J. Solut. Chem. 1983, 12, 161.
65. Covington, A. K.; Freeman, J. G.; Lilley, T. H. J. Phys. Chem. 1970, 74, 3773.
66. Delsigore, M.; Maaser, H. E.; Petrucci, S. J. Phys. Chem. 1984, 88, 2405.
67. Khalzaeli, S.; Popov, A. I.; Dye, J. L. J. Phys. Chem. 1982, 86, 4238.
68. Fuoss, R. M. J. Am. Chem. Soc. 1935, 57, 388.
69. Kamlet, M. J.; Abboud, J. L.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877.
70. Weller, A. Z. Phys. Chem. (Wiesbaden) 1982, 133, 93.
71. Fuoss, R. M. J. Phys. Chem. 1978, 82, 2427.
72. Maryott, A. A.; Smith, E. R. Table of Dielectric Constants of Pure Liquids; U.S. Government Printing Office: Washington, DC, 1951.
73. Gibson, J. Sovent Extraction and Liquid Membrane. Properties of Trioctyl Phosphate. M.A. Thesis, University of Minnesota, 1982.
74. Bollinger, J. C.; Yvernauli, G.; Ynernault, T. J. Solut. Chem. 1978, 7, 317.
75. Flick, E. W. Industrial Solvents Handbook; Noyes Data Corp.: Park Ridge, NJ, 1991.
76. Laurence, C.; Nicolet, P.; Dalati, M. T.; Abboud, J.-L. M.; Notario, R. J. Phys. Chem. 1994, 98, 5807.