The coordination chemistry of fluorine in fluorocarbons

ChemBioChem

Volumn 5, Issue 5, 2004, Pages 650-655

  Plenio, Herbert ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Alkali metals; Alkaline earth metals; Coordination chemistry; Flourine containing drugs

Indexed keywords

AMODIAQUINE; ANALGESIC AGENT; ANTIMALARIAL AGENT; ANXIOLYTIC AGENT; COORDINATION COMPOUND; DIAZEPAM; FLUORINE; FLUOROCARBON; FLUOROURACIL; HERBICIDE; LIGAND; METAL ION; PARACETAMOL;

CRYSTAL STRUCTURE; DATA BASE; FLUORINATION; HYDROGEN BOND; MATHEMATICAL GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SHORT SURVEY; STRUCTURE ANALYSIS;

CROWN ETHERS; CRYSTALLOGRAPHY, X-RAY; FLUORINE; FLUOROCARBONS; HYDROCARBONS, FLUORINATED; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; METALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 4544345504     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300752     Document Type: Short Survey

References (50)

1. T. Hiyama, Organofluorine Compounds: Chemistry Applications, Springer, Berlin, 2000.
2. B. K. Park, N. R. Kitteringham, P. M. O'Neill, Ann. Rev. Pharmacol. Toxicol. 2001, 41, 443.
3. a) R. Filler in Organofluorine Compounds in Medicinal Chemistry (Ed.: R. Filler), Elsevier, Amsterdam, 1993, p. 1;
4. b) "Biomedical Frontiers of Fluorine Chemistry" K. L. Kirk, R. Filler, ACS Symp. Ser. 1996, 232, 1;
5. c) B. K. Park, N. R. Kitteringham, Drug Metab. Rev. 1994, 26, 605.
6. H. L. Carrell, J. P. Glusker, J. J. Villafranca, A. S. Mildvan, R. J. Dummel, E. Kun, Science 1970, 170, 1412.
7. A. Karipides, C. Miller, J. Am. Chem. Soc. 1984, 106, 1494.
8. P. Murray-Rust, I. P. William, C. Stallings, C. T. Monti, R. K. Preston, J. P. Glusker, J. Am. Chem. Soc. 1983, 105, 3206.
9. H. Plenio, Chem. Rev. 1997, 97, 3363.
10. Chemical Hardness, Structure and Bonding, Vol. 80 (Ed.: K. D. Sen), Springer, Berlin, 1993.
11. B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, VCH, Weinheim, 1993.
12. H. Plenio, R. Diodone, Angew. Chemie. 1994, 106, 2267; Angew. Chem. Int. Ed. 1994, 33, 2175.
13. H. Plenio, R. Diodone, Angew. Chemie. 1994, 106, 2267; Angew. Chem. Int. Ed. 1994, 33, 2175.
14. H. Plenio, R. Diodone, J. Am. Chem. Soc. 1996, 118, 356.
15. H. Plenio, R. Diodone, Chem. Ber. 1997, 130, 963.
16. a) H. Plenio, D. Burth, J. Chem. Soc. Chem. Commun. 1994, 2297;
17. b) H. Plenio, R. Diodone, Z. Naturforsch. 1995, 50b, 1075;
18. c) H. Plenio, Inorg. Chem. 1994, 33, 6123.
19. J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89.
20. J. D. Dunitz, ChemBioChem 2004, 5, ■■.
21. H. Plenio, R. Diodone, Chem. Ber. 1997, 130, 633.
22. 19F NMR shift.
23. 19F NMR-Spektroskopie Thieme, Stuttgart, 1994
24. H. Plenio, R. Diodone, Chem. Ber. 1996, 129, 1211.
25. H. Takemura, N. Kon, M. Kotoku, S. Nakashima, K. Otsuka, M. Yasutake, T. Shinmyozu, T. Inazu, J. Org. Chem. 2001, 66, 2778.
26. W. A. W. A. Bakar, J. L. Davidson, W. E. Lindsell, K. J. McCullough, K. W. Muir, J. Chem. Soc. Dalton Trans. 1989, 991.
27. Structural drawings were produced by using ORTEP-3, L. J. Farugia, University of Glasgow and POVRAY V3.5.
28. H. Plenio, J. Hermann, R. Diodone, Inorg. Chem. 1997, 36, 5722.
29. H. Plenio, R. Diodone, D. Badura, Angew. Chem. 1997, 109, 130; Angew. Chem. Int. Ed. 1997,36, 156.
30. H. Plenio, R. Diodone, D. Badura, Angew. Chem. 1997, 109, 130; Angew. Chem. Int. Ed. 1997,36, 156.
31. a) H. Takemura, S. Nakashima, N. Kon, M. Yasutake, T. Shinmyozu, T. Inazu, J. Am. Chem. Soc. 2001, 123, 9293;
32. b) H. Takemura, N. Kon, M. Yasutake, H. Kariyazono, T. Shinmyozou, T. Inazu, Angew. Chem. 1999, 111, 1012; Angew. Chem. Int. Ed. 1999, 38, 959.
33. b) H. Takemura, N. Kon, M. Yasutake, H. Kariyazono, T. Shinmyozou, T. Inazu, Angew. Chem. 1999, 111, 1012; Angew. Chem. Int. Ed. 1999, 38, 959.
34. H. Takemura, J. Syn. Org. Chem. Jpn. 2002, 60, 963.
35. Y. Habata, T. Saeki, S. Akabori, X. X. Zhang, J. S. Bradshaw, Chem. Commun. 2000, 1469.
36. B. P. Hay, J. R. Rustad, J. Am. Chem. Soc. 1994, 116, 6316.
37. Cambridge Structural Database, Version November 22, 2002. F. H. Alien, W. D. S. Motherwell, Acta Crystallogr. 2002, 858, 407.
38. + contacts (total number 79) is by far the largest among the group I and II metal ions.
39. The CSD reference codes of the structures are as follows: BUXTAP, CUBYED, DENZAX, DOLJUJ; FPYRVH, HAGYAP, HAGYIX, HAGYOD, JIWVIU, NAWAH, NEHCEI, NIQJAY, RAWXOC, REJBAJ, REJBEN, REZGEI, RUVFET, VOVDOZ, YOXTUA01, ZAQZII, ZAWMEP, ZOHYAW, ZOHYEA, ZUVQIQ, ZUVQOW.
40. H. J. Buschmann, J. Hermann, M. Kaupp, H. Plenio, Chem. Eur. J. 1999, 5, 2S66.
41. R. Amunugama, M. T. Rodgers, J. Phys. Chem. A 2002, 106, 9092.
42. E. S. Meadows, S. L. de Wall, L. J. Barbour, G. W. Gokel, J. Am. Chem. Soc. 2001, 123, 3092.
43. J. A. Samuels, E. B. Lobkovsky, W. Streib, K. Foiling, J. C. Huffman, J. W. Zwanziger, K. G. Caulton, J. Am. Chem. Soc. 1993, 115, 5093.
44. a) J. Burdeniuc, B. Jedlicka, R. H. Crabtree, Chem. Ber. 1997, 130, 145;
45. b) T. G. Richmond, Angew. Chem. 2000, 112, 3378; Angew. Chem. Int. Ed. 2000, 39, 3241.
46. b) T. G. Richmond, Angew. Chem. 2000, 112, 3378; Angew. Chem. Int. Ed. 2000, 39, 3241.
47. a) N. Kleigrewe, T. Brackemeyer, G. Kehr, R. Fröhlich, G. Erker, Organometallics 2001, 20, 1952;
48. b) X. Yang, C. L. Stern, T. J. Marks, Organometallics 1991, 10, 840.
49. J. J. R. Frausto da Suva, R. J. P. Williams, The Biological Chemistry of the Elements, Clarendon, Oxford, 2001.
50. H. Weychardt, H. Plenio, unpublished results.