Cofacial phenylene donors as novel organic sensors for the reversible binding of nitric oxide

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8630-8631

  Rathore, Rajendra ^a   Kochi, Jay K ^a  

^a University of Houston ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; NITRIC OXIDE;

ARTICLE; CHEMICAL BINDING; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0031767228     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981589b     Document Type: Article

References (32)

1. Rathore, R.; Lindeman, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. Engl. 1998, 37, 1585. Compare: Kim, E. K.; Kochi, J. K. J. Am. Chem. Soc. 1991, 113, 4962.
2. Rathore, R.; Lindeman, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. Engl. 1998, 37, 1585. Compare: Kim, E. K.; Kochi, J. K. J. Am. Chem. Soc. 1991, 113, 4962.
3. + (2 mM) by cyclic voltammetry in dichloromethane (containing 0.2 M tetra-n-butylammonium hexafluorophosphate as supporting electrolyte).
4. (a) Suzuki, T.; Kondo, M.; Nakamura, T.; Fukushima, T.; Miyashi, T. J. Chem. Soc., Chem. Commun. 1997, 2325.
5. (b) Suzuki, T.; Takahashi, H.; Nishida, J.; Tsuji, T. J. Chem. Soc., Chem. Commun. 1998, 1331.
6. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154 and references therein.
7. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 198. Also see: Feringa, B. L.; Jager, W. F.; de Lange, B. Tetrahedron 1993, 49, 8267.
8. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 198. Also see: Feringa, B. L.; Jager, W. F.; de Lange, B. Tetrahedron 1993, 49, 8267.
9. (a) Feldman, P. L.; Griffith, O. W.; Stuehr, D. J. Chem. Eng. News 1993, Dec. 20, 26.
10. (b) Culotta, E.; Koshland, Jr., D. E. Science 1992, 258, 1862 and references therein.
11. (e) Keefer, L. K. CHEMTECH 1998, 28, 30.
12. (a) The molecular structures of the rigid triptycene donors in Chart 1 are presented with the aid of the QUANTA graphics (Molecular Simulation Inc., 16 New England Executive Park, Burlington, MA 01803).
13. 30: C, 90.51; H, 9.49. Found: C, 90.32; H, 9.21.
14. 30: C, 90.51; H, 9.49. Found: C, 90.32; H, 9.21.
15. •+ as the hexachloroantimonate salt, see: Rathore, R.; Kumar, A. S.; Lindeman, S. V.; Kochi, J. K. J. Org. Chem. 1998, 63, 5847.
16. -1. See: (a) Fateley, W. G.; Bent, H. A.; Crawford, B., Jr. J. Chem. Phys. 1959, 37, 204. (b) Laane, J.; Ohlsen, J. R. Prog. Inorg. Chem. 1980, 27, 465.
17. -1. See: (a) Fateley, W. G.; Bent, H. A.; Crawford, B., Jr. J. Chem. Phys. 1959, 37, 204. (b) Laane, J.; Ohlsen, J. R. Prog. Inorg. Chem. 1980, 27, 465.
18. +. An X-ray structural study in progress should establish this point.
19. max = 640 nm.
20. Bosch, E.; Rathore, R.; Kochi, J. K. J. Org Chem. 1994, 59, 2529.
21. As hexachloroantimonate salt.
22. +, as judged by the UV-vis absorption spectroscopy. However, prolonged heating of the purple solution (at >40 °C) led to the irreversible bleaching of the color.
23. 0 = 1.34 V vs SCE or by chemical oxidation with a mixture of chloranil and methanesulfonic acid in dichloromethane (Rathore, R.; Kochi, J. K. Acta Chem. Scand. 1998, 52, 114).
24. max = 365 and 560 (br) nm, did not release its bound NO at room temperature.
25. - was also determined at -30 °C, and details are on deposit and can be obtained from the Cambridge Crystallographic Data Center].
26. (a) Keck, D. B.; Hause, C. D. J. Mol. Spectrosc. 1968, 26, 163.
27. ar distance (1.414 Å).
28. eq) of 0.017) and O (0.030) relative to those of methyl carbons (0.039).
29. 22 merits further scrutiny.
30. Rathore, R.; Bosch, E.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1994, 1157.
31. Rathore, R. To be published.
32. 0 = 1.36, 0.98, 1.40, and 1.21 V vs SCE, respectively, show temperature-dependent binding of NO analogous to that described in eq 3 (except at lower temperatures of <-50 °C).