On the Mechanism of Radical C-N Coupling in Type B Semiconductor Photocatalysis: A High-Pressure Study

Journal of Physical Chemistry B

Volumn 104, Issue 5, 2000, Pages 1014-1024

  Reinheimer, Arne ^a   Van Eldik, Rudi ^a   Kisch, Horst ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001616412     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp992702k     Document Type: Article

References (72)

1. Künneth, R.; Feldmer, C.; Knoch, F.; Kisch, H. Chem.-Eur. J. 1995, 1, 441.
2. (a) Schindler, W.; Knoch, F.; Kisch, H. Chem. Ber. 1996, 129, 925.
3. (b) Schindler, W.; Kisch, H. J. Photochem. Photobiol. A: Chem. 1997, 103, 257.
4. (c) Keck, H.; Schindler, W.; Knoch, F.; Kisch, H. Chem.-Eur. J. 1997, 3, 1638.
5. Schindler, W.; Kisch, H. Unpublished.
6. Jin, Z.; Li, Q.; Zheng, X.; Xi, C.; Wang, C.; Zhang, H.; Feng, L.; Wang, H.; Chen, Z.; Jiang, Z. J. Photochem. Photohiol. A: Chem. 1993, 71, 85.
7. Hiemenz, P. C. Principles of Colloidal and Surface Chemistry, 2nd ed.; M. Decker: New York, 1986.
8. The reaction rates of 1 and 2 decreased by 96% and 84%, respectively.
9. Weber, W. Rheol. Acta 1975, 14, 1012.
10. (a) Cunningham, J.; Srijaranai, S. J. Photochem. Photobiol. A: Chem. 1991, 58, 361.
11. (b) Cunningham, J.; Sedlák, P. J. Photochem. Photobiol. A: Chem. 1994, 77, 255.
12. (c) Cunningham, J.; Al-Sayyed, G. J. Chem. Soc., Faraday Trans. 1990, 86, 3935.
13. Hörner, G.; Johne, P.; Künneth, R.; Twardzik, G.; Kisch, H. Chem.-Eur. J. 1999, 5, 208.
14. Mills, A.; Williams, G. J. Chem. Soc., Faraday Trans. 1 1987, 83, 2647.
15. Al-Ekabi, H.; de Mayo, P. Tetrahedron 1986, 42, 6277.
16. Ali, I. T.; Gay, I. D. J. Phys. Chem. 1981, 85, 1251.
17. (a) Michels, J. J.; Dorsey, J. G. Langmuir 1990, 6, 414.
18. (b) Tavener, S. J.; Clark, J. H.; Gray, G. W.; Heath, P. A.; Macquarrie, D. J. Chem. Commun. 1997, 1147.
19. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 1st ed.; VCH: Weinheim, 1988; p 364.
20. Iler, R. K. The Chemistry of Silica; John Wiley: New York, 1979; p 648.
21. Ponec, V.; Knor, Z.; Cerný, S. Adsorption on Solids; Butterworths: London, 1974.
22. 13CNMR-Spektroskopie; Georg Thieme Verlag: Stuttgart, New York, 1984.
23. (b) Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York, London, 1972.
24. (c) Günther, H. NMR-Spektroskopie; Georg Thieme Verlag: Stuttgart, New York, 1984.
25. Calculation was carried out analogous to ref 21, assuming a hexagonal quartz structure.
26. Hiemstra, T.; van Riemsdijk, W. H. J. Colloid. Interface Sci. 1989, 136, 132.
27. -1 of the silica used in this work.
28. -1. Chan, D.; Perram, J. W.; White, L. R.; Healy, T. W. J. Chem. Soc., Faraday Trans. 1 1975, 1046.
29. (b) Data from ASTM-card-index.
30. N value of 2,5-DHF should be in the range of 0.164 to 0.270, corresponding to furan and THF, respectively,
31. (b) See: Lide, D. R.; Raton, H. P. R. Handbook of Chemistry and Physics, 75th ed.; CRC Press: Boca Raton, 1994.
32. Hörner, G.; Kisch, H. Unpublished.
33. Estimated from a molecular model as 0.24 nm × 0.38 nm.
34. Estimated from a molecular model as 0.46 nm × 0.45 nm.
35. Estimated from a molecular model as 1.08 nm × 0.48 nm.
36. Since in the dark adsorption experiments light could not be completely excluded, cis-azobenzene was present in about 1%.
37. Reinheimer, A.; Fernández, A.; Kisch, H. Z. Phys. Chem. 1999, 213 (II), 129.
38. Park, S. W.; Huang, C. P. J. Colloid. Interface Sci. 1987, 117, 431.
39. Bandosz, T. J.; Lin, C.; Ritter, J. A. J. Colloid. Interface Sci. 1998, 198, 347.
40. Reinheimer, A.; Kisch, H. Unpublished.
41. Zeug, N.; Bücheier, J.; Kisch, H. J. Am. Chem. Soc. 1985, 107, 1459.
42. •) = + 2.4 V) may occur according to eq 6.
43. Endres, U.; Kisch, H. Unpublished.
44. (a) Anpo, M.; Matsumoto, A.; Kodama, S. J. Chem. Soc., Chem. Commun. 1987, 1038.
45. (b) Nakaoka, Y.; Nosaka, Y. J. Phys. Chem. 1995, 99, 9893.
46. (c) Kamat, P. V.; Dimitrijevic, N. M.; Fessenden, R. W. J. Phys. Chem. 1987, 91, 396.
47. Lunazzi, L.; Placucci, G.; Grossi, L. Tetrahedron 1983, 39, 159.
48. Du, X.; Arnold, D. R.; Boyd, R. J.; Shi, Z. Can. J. Chem. 1991, 69, 1365.
49. Kojima, M.; Kakehi, A.; Ishida, A.; Takamuku, S. J. Am. Chem. Soc. 1996, 118, 2612.
50. Shono, T.; Ikeda, A. J. Am. Chem. Soc. 1972, 94, 7892.
51. Aylward, G. H.; Findlay, T. J. V. Datensammlung Chemie in SI-Einheiten, 2nd ed.; VCH: Weinheim, 1986.
52. Yoshida, K.; Kanbe, T.; Fueno, T. J. Org. Chem. 1977, 42, 2313.
53. Miles, H. H. J. Electroanal. Chem. Interfacial Electrochem. 1975, 60, 84.
54. The alternative, that the byproduct is the isomeric 2-methoxy-1-phenylcyclohexane is unlikely. Since its formation occurs by solvent attack on the radical cation, as demonstrated in the homogeneous reaction with cerium(IV), it already should have been formed in the photoreaction with unmodified CdS-A.
55. A value can be estimated following: Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1989, 111, 8646.
56. Schäfer, K. Landolt-Börnstein, Zahlenwerte und Funktionen; Springer: Berlin, 1969; Vol. 6, Board II/5a.
57. (a) Srinivasan, K. R.; Kay, R. L. J. Solution Chem. 1977, 6, 357.
58. (b) See ref 45.
59. (c) Brazier, D. W.; Freeman, G. R. Can. J. Chem. 1969, 47, 893.
60. (d) Gowikberg, M. G. Chemical Equilibria and Reaction Rates at High Pressure, 2nd ed.; Moskwa, 1960.
61. Miyahara, M.; Iwasaki, S.; Kotera, T.; Kawamura, T.; Okazaki, M. J. Colloid Interface Sci. 1995, 170, 335.
62. Williams, M. E.; Crooker, J. C.; Pyati, R.; Lyons, L. J.; Murray, R. W. J. Am. Chem. Soc. 1997, 119, 10249.
63. Anderson, O. S.; Feldberg, S. W. J. Phys. Chem. 1996, 100, 4622.
64. (a) Asano, T.; de Noble, W. J. Chem. Rev. 1978, 78, 407.
65. (b) van Eldik, R.; Asano, T.; le Noble, W. J. Chem. Rev. 1989, 89, 549.
66. (c) Drljaca, A.; Hubbard, C. D.; van Eldik, R.; Asano, T.; Basilevsky, M. V.; le Noble, W. J. Chem. Rev. 1998, 98, 2167.
67. Isaacs, N. S. Liquid-Phase High-Pressure Chemistry; John Wiley & Sons: Chichester, New York, Brisbane, Toronto, 1981.
68. (a) Nicholson, A. E.; Norrish, G. W. Discussions Faraday Soc. 1956, 22, 104.
69. (b) Yokawa, M.; Ogo, Y. Makromol. Chem. 1976, 177, 429.
70. Reference 51, p 106.
71. Spitzer, M.; Gärtig, F.; van Eldik, R. Rev. Sci. Instrum. 1988, 59, 2092.
72. le Noble, W. J.; Schlott, R. Rev. Sci. Instrum. 1976, 47, 770.