Perfluorocarbon-hydrocarbon self-assembly. Part 6:1 α,ω-diiodoperfluoroalkanes as pseudohalogens in supramolecular synthesis

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7519-7523

  Corradi, Eleonora ^a   Meille, Stefano Valdo ^a   Messina, Maria Teresa ^a   Metrangolo, Pierangelo ^a   Resnati, Giuseppe ^a  

^a Dipartimento di Chimica   (Italy)

Author keywords

Donors; Fluorine; Halogens; Supramolecular chemistry

Indexed keywords

ALKANE DERIVATIVE; BIPYRIDINE DERIVATIVE; FLUORINE; FLUOROCARBON; HALOGEN; HYDROCARBON;

ARTICLE; CHEMICAL MODIFICATION; CRYSTAL; MOLECULAR INTERACTION; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033569871     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01479-3     Document Type: Article

References (39)

1. Part 5: Farina, A.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 2433.
2. Hassel, O. Science 1970, 170, 497. Bent, H. A. Chem. Rev. 1968, 68, 587. Foster, R. Organic Charge-Transfer Complexes; Academic Press: London, 1969.
3. Hassel, O. Science 1970, 170, 497. Bent, H. A. Chem. Rev. 1968, 68, 587. Foster, R. Organic Charge-Transfer Complexes; Academic Press: London, 1969.
4. Hassel, O. Science 1970, 170, 497. Bent, H. A. Chem. Rev. 1968, 68, 587. Foster, R. Organic Charge-Transfer Complexes; Academic Press: London, 1969.
5. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
6. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
7. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
8. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
9. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
10. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
11. Muravlyanskii, D. V.; Gur'yanova, E. N.; Romm, I. P.; Sviridov, B. D.; Shcherbakova, E. S. Zh. Obshch. Khim. 1986, 56, 1299 (Chem. Abstr. 1987, 106, 66680k). Soled, S.; Carpenter, G. B. Acta Crystallogr., Sect. B 1974, 30, 910. Okishi, Y.; Imai, Y.; Aida, K. J. Inorg. Nucl. Chem. 1973, 35, 101. Yarwood, J.; Person, W. B. J. Am. Chem. Soc. 1968, 90, 3930. Yagi, Y.; Popov, A. I. J. Am. Chem. Soc. 1965, 87, 3577. Whitaker, R. D.; Ambrose, J. R.; Hickam, C. W. J. Inorg. Nucl. Chem. 1961, 17, 254.
12. Tebbe, K. F.; Graefe-Kavoosian, A. Z. Naturforsch., Teil B 1996, 51, 1007.
13. Jander, J.; Maurer, A. Z. Naturforsch., Teil B 1978, 33, 1446.
14. (a) Bailey, R. D.; Drake, G. W.; Grabarczyk, M.; Hanks, T. W.; Hook, L. L.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 2 1997, 2773. (b) Wynter, C. I.; Hill, J.; Bledsoe, W. J. Chem. Phys. 1969, 50, 3872. (c) Yagi, Y.; Popov, A. I. J. Phys. Chem. 1967, 71, 2439. (d) Popov, A. I.; Marshall, J. C.; Stute, F. B.; Person, W. B. J. Am. Chem. Soc. 1961, 83, 3586. (e) Person, W. B.; Humphrey, R. E.; Popov, A. I. J. Am. Chem. Soc. 1959, 81, 273.
15. (a) Bailey, R. D.; Drake, G. W.; Grabarczyk, M.; Hanks, T. W.; Hook, L. L.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 2 1997, 2773. (b) Wynter, C. I.; Hill, J.; Bledsoe, W. J. Chem. Phys. 1969, 50, 3872. (c) Yagi, Y.; Popov, A. I. J. Phys. Chem. 1967, 71, 2439. (d) Popov, A. I.; Marshall, J. C.; Stute, F. B.; Person, W. B. J. Am. Chem. Soc. 1961, 83, 3586. (e) Person, W. B.; Humphrey, R. E.; Popov, A. I. J. Am. Chem. Soc. 1959, 81, 273.
16. (a) Bailey, R. D.; Drake, G. W.; Grabarczyk, M.; Hanks, T. W.; Hook, L. L.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 2 1997, 2773. (b) Wynter, C. I.; Hill, J.; Bledsoe, W. J. Chem. Phys. 1969, 50, 3872. (c) Yagi, Y.; Popov, A. I. J. Phys. Chem. 1967, 71, 2439. (d) Popov, A. I.; Marshall, J. C.; Stute, F. B.; Person, W. B. J. Am. Chem. Soc. 1961, 83, 3586. (e) Person, W. B.; Humphrey, R. E.; Popov, A. I. J. Am. Chem. Soc. 1959, 81, 273.
17. (a) Bailey, R. D.; Drake, G. W.; Grabarczyk, M.; Hanks, T. W.; Hook, L. L.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 2 1997, 2773. (b) Wynter, C. I.; Hill, J.; Bledsoe, W. J. Chem. Phys. 1969, 50, 3872. (c) Yagi, Y.; Popov, A. I. J. Phys. Chem. 1967, 71, 2439. (d) Popov, A. I.; Marshall, J. C.; Stute, F. B.; Person, W. B. J. Am. Chem. Soc. 1961, 83, 3586. (e) Person, W. B.; Humphrey, R. E.; Popov, A. I. J. Am. Chem. Soc. 1959, 81, 273.
18. (a) Bailey, R. D.; Drake, G. W.; Grabarczyk, M.; Hanks, T. W.; Hook, L. L.; Pennington, W. T. J. Chem. Soc., Perkin Trans. 2 1997, 2773. (b) Wynter, C. I.; Hill, J.; Bledsoe, W. J. Chem. Phys. 1969, 50, 3872. (c) Yagi, Y.; Popov, A. I. J. Phys. Chem. 1967, 71, 2439. (d) Popov, A. I.; Marshall, J. C.; Stute, F. B.; Person, W. B. J. Am. Chem. Soc. 1961, 83, 3586. (e) Person, W. B.; Humphrey, R. E.; Popov, A. I. J. Am. Chem. Soc. 1959, 81, 273.
19. 19F NMR) and in the solid (IR, Raman, DSC, X-ray), spectral and physical properties quite similar to those of analogous co-crystals 3a-d. This proves that hydrocarbon diheteroaromatic compounds are a motif of general effectiveness in the construction of perfluorocarbon-hydrocarbon architectures with a pre-established topology.
20. Amico, V.; Meille, S. V.; Corradi, E.; Messina, M. T.; Resnati, G. J. Am. Chem. Soc. 1998, 120, 8261. Lunghi, A.; Cardillo, P.; Messina, M. T.; Metrangolo, P.; Panzeri, W.; Resnati, G. J. Fluorine Chem. 1998, 91, 191. Messina, M. T.; Metrangolo, P.; Resnati, G. In Asymmetric Fluoro-Organic Chemistry: Synthesis, Applications, and Future Directions; ACS Symposium Series n. 603, American Chemical Society: Washington, DC, 1999.
21. Amico, V.; Meille, S. V.; Corradi, E.; Messina, M. T.; Resnati, G. J. Am. Chem. Soc. 1998, 120, 8261. Lunghi, A.; Cardillo, P.; Messina, M. T.; Metrangolo, P.; Panzeri, W.; Resnati, G. J. Fluorine Chem. 1998, 91, 191. Messina, M. T.; Metrangolo, P.; Resnati, G. In Asymmetric Fluoro-Organic Chemistry: Synthesis, Applications, and Future Directions; ACS Symposium Series n. 603, American Chemical Society: Washington, DC, 1999.
22. Amico, V.; Meille, S. V.; Corradi, E.; Messina, M. T.; Resnati, G. J. Am. Chem. Soc. 1998, 120, 8261. Lunghi, A.; Cardillo, P.; Messina, M. T.; Metrangolo, P.; Panzeri, W.; Resnati, G. J. Fluorine Chem. 1998, 91, 191. Messina, M. T.; Metrangolo, P.; Resnati, G. In Asymmetric Fluoro-Organic Chemistry: Synthesis, Applications, and Future Directions; ACS Symposium Series n. 603, American Chemical Society: Washington, DC, 1999.
23. ICF2CF2CF2CF2-=0.03.
24. Messina, M. T.; Metrangolo, P.; Panzeri, W.; Ragg, E.; Resnati, G. Tetrahedron Lett. 1998, 39, 9069.
25. -1 when 2a is halogen bonded with bipyridine 1 in co-crystal 3a.
26. Larsen, D. W.; Allred, A. L. J. Phys. Chem. 1965, 69, 2400.
27. -3. X-Ray diffraction data were collected from colourless crystal platelets with graphite monochromated Cu-Kα radiation (1.54178 Å). The structure was solved by direct methods using SIR92 (Ref. 13) and refined by full-matrix least squares on F2, using SHELXL97 (Ref. 14). Non hydrogen atoms were refined anisotropically; hydrogen atoms were located at calculated positions and refined in the riding mode. Relatively high values of the residual factors may reflect poor crystal quality or disorder.
28. Altomare, A.; Cascarano, G.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
29. Sheldrick, G. SHELXL97, Program for Crystal Structure Refinement; University of Göttingen, Germany, 1997.
30. Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press: New York, 1994.
31. Bondi, A. J. Phys. Chem. 1964, 68, 441.
32. Padmanabhan, K.; Paul, I. E.; Curtin, D. Y. Acta Crystallogr., Sect. C 1990, 46, 88.
33. Bailey, R. D.; Buchanan, M. L.; Pennington, W. D. Acta Crystallogr., Sect. C. 1992, 48, 2259.
34. Uchida, T.; Kimura, K. Acta Crystallogr., Sect. C. 1984, 40, 139.
35. Bunn, C. W.; Howells, E. S. Nature 1954, 174, 549.
36. Dixon, D. A. J. Phys. Chem. 1992, 96, 3968.
37. Caronna, T.; Corradi, E.; Meille, S. V.; Novo, B.; Resnati, G.; Sidoti, G. J. Fluorine Chem. 1999, 97, 183.
38. Haszeldine, R. N. J. Chem. Soc. 1953, 2622.
39. Prakash, G. K. S.; Krishnamurty, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393.