An efficient venus flytrap for the reversible binding of nitric oxide

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1585-1587

  Rathore, Rajendra ^a   Lindeman, Sergey V ^a   Kochi, Jay K ^a  

^a NONE

Author keywords

Host guest chemistry; Molecular tweezers; Nitric oxide; Noncovalent interactions

Indexed keywords

EID: 0032546763     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1585::AID-ANIE1585>3.0.CO;2-W     Document Type: Article

References (31)

1. a) D. J. Cram, Nature 1992, 356, 29;
2. b) Angew. Chem. 1988, 100, 1041; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009, and references therein;
3. b) Angew. Chem. 1988, 100, 1041; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009, and references therein;
4. c) J.-M. Lehn, ibid. 1988, 100, 91 and 1988, 27, 90, and references therein;
5. c) J.-M. Lehn, ibid. 1988, 100, 91 and 1988, 27, 90, and references therein;
6. d) C. A. Hunter, ibid. 1995, 107, 1687; 1995, 34, 1679;
7. d) C. A. Hunter, ibid. 1995, 107, 1687; 1995, 34, 1679;
8. e) R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485;
9. f) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487, and references therein.
10. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 2495; 7017.
11. D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154, and references therein.
12. D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154, and references therein.
13. a) E. Culotta, D. E. Koshland, Jr. Science 1992, 258, 1862;
14. b) P. L. Feldman, O. W. Griffith, D. J. Stuehr, Chem. Eng. News 1993, 71(52), 26.
15. The term "Venus flytrap" has also been used to describe the calix[4]arene-based host of ethyl acetate (J. R. Atwood, G. W. Orr, G. G. Bott, K. D. Robinson, Angew. Chem. 1993, 105, 1114; Angew. Chem. Int. Ed. Engl. 1993, 32, 1093) and the porphyrin-based trap for pyridine (M. Mazzanti, J.-C. Marchon, J. Am. Chem. Soc. 1997, 119, 12400).
16. The term "Venus flytrap" has also been used to describe the calix[4]arene-based host of ethyl acetate (J. R. Atwood, G. W. Orr, G. G. Bott, K. D. Robinson, Angew. Chem. 1993, 105, 1114; Angew. Chem. Int. Ed. Engl. 1993, 32, 1093) and the porphyrin-based trap for pyridine (M. Mazzanti, J.-C. Marchon, J. Am. Chem. Soc. 1997, 119, 12400).
17. The term "Venus flytrap" has also been used to describe the calix[4]arene-based host of ethyl acetate (J. R. Atwood, G. W. Orr, G. G. Bott, K. D. Robinson, Angew. Chem. 1993, 105, 1114; Angew. Chem. Int. Ed. Engl. 1993, 32, 1093) and the porphyrin-based trap for pyridine (M. Mazzanti, J.-C. Marchon, J. Am. Chem. Soc. 1997, 119, 12400).
18. See also J. E. Gano, G. Subramaniam, R. Birnbaum, J. Org. Chem. 1990, 55, 4760. Also note that the double bond in VFT is completely entombed by the bicyclooctene framework and the vicinal phenyl groups (containing four ortho methyl groups), which render it completely inert toward a variety of electrophiles.
19. ox = 1.27 V versus the standard calomel electrode (SCE) and as well as chemically with either the stable cation radical of 9,10-dimethoxy-1,4:5,8-diethano-1,2,3,4,5,6,7,8-octahydroanthracene (R. Rathore, J. K. Kochi, J. Org. Chem. 1995, 60, 4399) or with a mixture of chloranil and methane-sulfonic acid in dichloromethane (R. Rathore, J. K. Kochi, Acta. Chem. Scand. 1998, 52, 114).
20. ox = 1.27 V versus the standard calomel electrode (SCE) and as well as chemically with either the stable cation radical of 9,10-dimethoxy-1,4:5,8-diethano-1,2,3,4,5,6,7,8-octahydroanthracene (R. Rathore, J. K. Kochi, J. Org. Chem. 1995, 60, 4399) or with a mixture of chloranil and methane-sulfonic acid in dichloromethane (R. Rathore, J. K. Kochi, Acta. Chem. Scand. 1998, 52, 114).
21. -1. See a) W. G. Fateley, H. A. Bent, B. Crawford, Jr., J. Chem. Phys. 1959, 31, 204; b) J. Laane, J. R. Ohlsen, Prog. Inorg. Chem. 1980, 27, 465.
22. -1. See a) W. G. Fateley, H. A. Bent, B. Crawford, Jr., J. Chem. Phys. 1959, 31, 204; b) J. Laane, J. R. Ohlsen, Prog. Inorg. Chem. 1980, 27, 465.
23. D. B. Keck, C. D. Hause, J. Mol. Spectrosc. 1968, 26, 163.
24. arene-NO bond distance in various nitrosoarenes is about 1.39 Å (Cambridge Crystallographic Database, Release Fall 1997).
25. +.
26. + they are bent towards each other.
27. + complex; see K. Y. Lee, D. J. Kuchynka, J. K. Kochi, Inorg. Chem. 1990, 29, 4196.
28. See, for comparison, E. K. Kim, J. K. Kochi, J. Am. Chem. Soc. 1991, 113, 4962.
29. The neutral hydrocarbon ligand VFT and NO do not interact, as shown by the absence of any color change upon saturation of a solution of VFT in dichloromethane with gaseous nitric oxide.
30. max = 349, 581 nm). To our knowledge, there are no other nonbiological systems for the reversible binding of nitric oxide.
31. R. Rathore, U. Weigand, J. K. Kochi, J. Org. Chem. 1996, 61, 5246.