Supramolecular steric effects as the means of making reactive carbon radicals persistent. Quantitative characterization of the external surface of MFI zeolites through a persistent radical probe and a langmuir adsorption isotherm

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1319-1330

  Hirano, Takashi ^a,d   Li, Wei ^a   Abrams, Lloyd ^b   Krusic, Paul J ^b   Ottaviani, M Francesca ^c   Turro, Nicholas J ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b DUPONT COMPANY   (United States)

^c UNIVERSITY OF URBINO   (Italy)

^d UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; CARBON; ETHANE; METHYL GROUP; RADICAL; TRITYL DERIVATIVE; ZEOLITE;

ADSORPTION; ARTICLE; CHEMICAL REACTION; DIMERIZATION; ELECTRON SPIN RESONANCE; MOLECULAR MODEL; PHOTOCHEMISTRY; PHOTOLYSIS; STEREOSPECIFICITY; SURFACE PROPERTY;

EID: 0034629386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991298i     Document Type: Article

References (43)

1. Gomberg, M. Ber. 1900, 33, 3150-3163; J. Am. Chem. Soc. 1900, 22, 757-771.
2. Gomberg, M. Ber. 1900, 33, 3150-3163; J. Am. Chem. Soc. 1900, 22, 757-771.
3. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1976, 9, 13-19.
4. McBride, J. M. Tetrahedron 1974, 30, 2009-2022.
5. Lehn, J. M. Supramolecular Chemistry; VCH: New York, 1995.
6. Davis, M. E.; Lobo, R. F. Chem. Mater. 1992, 4, 756-768.
7. Meier, W. M.; Olson, D. H. Atlas of Zeolite Structure Types; Butterworth-Heinemann: London, 1992.
8. Breck, D. W. Zeolite Molecular Sieves: Structure, Chemistry, and Use; Wiley and Sons: London, 1974.
9. Szostak, R. Molecular Sieves: Principle of Synthesis and Identification; Van Nostrand Reinhold: New York, 1989.
10. (a) Kokotailo, G. T.; Lawton, S. L.; Olson, D. H.; Meier, W. M. Nature (London) 1978, 272, 437-438.
11. (b) Olson, D. H.; Kokotailo, G. T.; Lawton, S. L.; Meier, W. M. J. Phys. Chem. 1981, 85, 2238-2243.
12. Flanigen, E. M.; Bennet, J. M.; Grose, R. W.; Cohen, J. P.; Patton, R. L.; Kirchner, R. M.; Smith, J. V. Nature (London) 1978, 272, 512-516.
13. (a) Turro, N. J.; Cheng, C.-C.; Mahler, W. J. Am. Chem. Soc. 1984, 106, 5022-5023.
14. (b) Turro, N. J.; Cheng, C.-C.; Abrams, L.; Corbin, D. R. J. Am. Chem. Soc. 1987, 109, 2449-2456.
15. Reviews: (a) Turro, N. J. Pure Appl. Chem. 1986, 58, 1219-1228.
16. (b) Ramamurthy, V.; Turro, N. J. J. Incl. Phenom. Mol. Recognit. Chem. 1995, 21, 239-282.
17. Photochemistry of dibenzyl ketone: (a) Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074-6076. (b) Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6076-6077. Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6077-6079. Photochemistry of tetraphenyl acetone: (a) Quinkert, G.; Opitz, K.; Weirdorff, W. W.; Weinlich, J. Tetrahedron Lett. 1963, 1863-1868.
18. Photochemistry of dibenzyl ketone: (a) Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074-6076. (b) Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6076-6077. Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6077-6079. Photochemistry of tetraphenyl acetone: (a) Quinkert, G.; Opitz, K.; Weirdorff, W. W.; Weinlich, J. Tetrahedron Lett. 1963, 1863-1868.
19. Photochemistry of dibenzyl ketone: (a) Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074-6076. (b) Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6076-6077. Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6077-6079. Photochemistry of tetraphenyl acetone: (a) Quinkert, G.; Opitz, K.; Weirdorff, W. W.; Weinlich, J. Tetrahedron Lett. 1963, 1863-1868.
20. Photochemistry of dibenzyl ketone: (a) Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074-6076. (b) Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6076-6077. Robbins, W. K.; Eastman, R. H.J. Am. Chem. Soc. 1970, 92, 6077-6079. Photochemistry of tetraphenyl acetone: (a) Quinkert, G.; Opitz, K.; Weirdorff, W. W.; Weinlich, J. Tetrahedron Lett. 1963, 1863-1868.
21. (b) Quinkert, G. Pure Appl. Chem. 1964, 9, 607-621.
22. (a) Turro, N. J.; Gould, I. R.; Baretz, B. H. J. Phys. Chem. 1983, 87, 531-532.
23. (b) Gould, I. R.; Baretz, B. H.; Turro, N. J. J. Phys. Chem. 1987, 91, 925-929.
24. Lunazzi, L.; Ingold, K. U.; Scaiano, J. C. J. Phys. Chem. 1983, 87, 529-530.
25. (a) Turro, N. J.; Lei, X.; Li, W.; McDermott, A.; Abrams, L.; Ottaviani, M. F.; Beard, H. S. Chem. Commun. 1998, 695-696.
26. (b) Turro, N. J.; McDermott, A.; Lei, X.; Li, W.; Abrams, L.; Ottaviani, M. F.; Beard, H. S.; Houk, K. N.; Beno, B. R.; Lee, P. S. Chem. Commun. 1998, 697-698.
27. (a) Kelly, G.; Willsher, C. J.; Wilkinson, F.; Netto-Ferreira, J. C.; Weir, A. O. D.; Johnston, L. J.; Scaiano, J. C. Can. J. Chem. 1990, 68, 812-819.
28. (b) Johnston, L. J.; Scaiano, J. C.; Shi, J.-L.; Siebrand, W.; Zerbetto, F. J. Phys. Chem. 1991, 95, 10018-10024.
29. Bassindale, A. R.; Bowles, A. J.; Hudson, A.; Jackson, R. A.; Schreiner, K.; Berndt, A. Tetrahedron Lett. 1973, 3185-3186.
30. Livingston, R.; Zeldes, H.; Conradi, M. S. J. Am. Chem. Soc. 1979, 101, 4312-4319.
31. Schlick, S.; Kevan, K. J. Phys. Chem. 1979, 83, 3424-3429.
32. Dixon, W. T.; Norman, R. O. C. J. Chem Soc. 1964, 4857-4860.
33. Fischer, H. Z. Naturforsch. A 1965, 20, 488-489.
34. Neta, P.; Schuler, R. H. J. Phys. Chem. 1973, 77, 1368-1370.
35. Oscik, J.; Cooper, I. L. Adsorption; Ellis Horwood Ltd, Chichester, 1982.
36. van Koningsveld, H.; Tuinstra, F.; van Bekkum, H.; Jansen, J. C. Acta Crystallogr., Sect. B 1989, B45, 423-431.
37. Fyfe, C. A.; Strobl, H.; Kokotailo, G. T.; Kennedy, G. J.; Barlow, G. E. J. Am. Chem. Soc. 1988, 110, 3373-3380.
38. Reischman, P. T.; Schmitt, K. D.; Olson, D. H. J. Phys. Chem. 1988, 92, 5165-5169.
39. (a) Wright, B. B.; Platz, M. S. J. Am. Chem. Soc. 1984, 106, 4175-4180.
40. (b) Zieger, H. E.; Angres, I.; Mathisen, D. J. Am. Chem. Soc. 1976, 98, 2580-2585.
41. Dean, D. O.; Dickinson, W. B.; Quayle, O. R.; Lester, C. T. J. Am. Chem. Soc. 1950, 72, 1740-1745.
42. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem. 1988, 53, 6077-6084.
43. Olah, G. A.; Surya Prakash, G. K. Synthesis 1978, 397-398.