Collect. Czech. Chem. Commun. 2002, 67, 1373-1382
https://doi.org/10.1135/cccc20021373

2,2':6',2''-Terpyridine as Monodentate Ligand: Halogen Bonding Driven Formation of Discrete 2 : 1 Aggregates with 1,2,4,5-Tetrafluoro-3,6-diiodobenzene

Rosalba Liantonioa, Thomas A. Logothetisa, Maria T. Messinaa, Pierangelo Metrangoloa,*, Alessandra De Santisa, Tullio Pilatib and Giuseppe Resnatia,*

a Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica "Giulio Natta", Via Mancinelli 7, I-20131 Milano, Italy
b C.N.R. - Istituto di Scienze e Tecnologie Molecolari, Università di Milano, Via Golgi 19, I-20133 Milano, Italy

References

1. Metrangolo P., Panzeri W., Recupero F., Resnati G.: J. Fluorine Chem. 2002, 114, 27. <https://doi.org/10.1016/S0022-1139(01)00558-9>
2a. Jeffrey G. A.: An Introduction to Hydrogen Bonding. Oxford University Press, Oxford 1997.
2b. Ermer O., Eling A.: J. Chem. Soc., Perkin Trans. 2 1994, 925. <https://doi.org/10.1039/p29940000925>
2c. Aakeröy C. B., Seddon K. R.: Chem. Soc. Rev. 1993, 22, 397. <https://doi.org/10.1039/cs9932200397>
3. Sauvage J.-P. (Ed.): Transition Metals in Supramolecular Chemistry. Wiley, Chichester 1999.
4. Lehn J.-M.: Supramolecular Chemistry: Concepts and Perspectives. VCH, Weinheim 1995.
5a. Desiraju G. R.: Angew. Chem., Int. Ed. Engl. 1995, 34, 2311. <https://doi.org/10.1002/anie.199523111>
5b. Desiraju G. R.: Chem. Commun. 1997, 1475. <https://doi.org/10.1039/a607149j>
6a. Simard M., Su D., Wuest J. D.: J. Am. Chem. Soc. 1991, 113, 4696. <https://doi.org/10.1021/ja00012a057>
6b. Su D., Wang X., Simard M., Wuest J. D.: Supramol. Chem. 1995, 6, 171. <https://doi.org/10.1080/10610279508032533>
7. Piguet C., Bernardinelli G., Hopfgarten G.: Chem. Rev. (Washington, D. C.) 1997, 97, 2005. <https://doi.org/10.1021/cr960053s>
8a. Deacon G. B., Patrick J. M., Skelton B. W., Thomas N. C., White A. H.: Aust. J. Chem. 1984, 37, 929. <https://doi.org/10.1071/CH9840929>
8b. Ferretti V., Gilli P., Bertolasi V., Marangoni G., Pitteri B., Chessa G.: Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1992, 48, 814. <https://doi.org/10.1107/S0108270191012830>
8c. Civitello E. R., Dragovich P. S., Karpishin T. B., Novick S. G., Bierach G., O’Connell J. F., Westmoreland T. D.: Inorg. Chem. 1993, 32, 237. <https://doi.org/10.1021/ic00054a022>
8d. Ramdeehul S., Barloy L., Osborn J. A., DeCian A., Fischer J.: Organometallics 1996, 15, 5442. <https://doi.org/10.1021/om9605894>
8e. Anderson P. A., Keene F. R., Horn E., Tiekink E. R. T.: Appl. Organomet. Chem. 1990, 4, 523. <https://doi.org/10.1002/aoc.590040514>
8f. Messina M. T., Metrangolo P., Resnati G., Quici S., Manfredi A., Pilati T.: Supramol. Chem. 2000, 12, 405. <https://doi.org/10.1080/10610270108027472>
9. Pruchnik F. P., Robert F., Jeannin Y., Jeannin S.: Inorg. Chem. 1996, 35, 4261. <https://doi.org/10.1021/ic950529a>
10a. Metrangolo P., Resnati G.: Chem. Eur. J. 2001, 7, 2511. <https://doi.org/10.1002/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T>
10b. Hassel O.: Science 1970, 170, 497. <https://doi.org/10.1126/science.170.3957.497>
10c. Dumas J. M., Gomel L., Guerin M.: The Chemistry of Functional Groups, Suppl. D (S. Patai and Z. Rappoport, Eds), p. 985. John Wiley and Sons, New York 1983.
10d. Bent H. A.: Chem. Rev. (Washington, D. C.) 1968, 68, 587. <https://doi.org/10.1021/cr60255a003>
10f. Legon A. C.: Angew. Chem., Int. Ed. 1999, 38, 2687. <https://doi.org/10.1002/(SICI)1521-3773(19990917)38:18<2686::AID-ANIE2686>3.0.CO;2-6>
11a. Farina A., Meille S. V., Messina M. T., Metrangolo P., Resnati G., Vecchio G.: Angew. Chem., Int. Ed. 1999, 38, 2433. <https://doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2433::AID-ANIE2433>3.0.CO;2-D>
11b. Weiss R., Rechinger M., Hampel F., Wolski A.: Angew. Chem., Int. Ed. 1995, 34, 441. <https://doi.org/10.1002/anie.199504411>
12a. Bloemink H. I., Legon A. C.: Chem. Eur. J. 1996, 2, 265. <https://doi.org/10.1002/chem.19960020306>
12b. Soled S., Carpenter G. B.: Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1974, 30, 910. <https://doi.org/10.1107/S0567740874004031>
12c. Okishi Y., Imai Y., Aida K.: J. Inorg. Nucl. Chem. 1973, 35, 101. <https://doi.org/10.1016/0022-1902(73)80615-3>
12d. Yarwood J., Person W. B.: J. Am. Chem. Soc. 1968, 90, 3930. <https://doi.org/10.1021/ja01017a005>
12e. Yagi Y., Popov A. I.: J. Am. Chem. Soc. 1965, 87, 3577. <https://doi.org/10.1021/ja01094a009>
12f. Whitaker R. D., Ambrose J. R., Hickam C. W.: J. Inorg. Nucl. Chem. 1961, 17, 254. <https://doi.org/10.1016/0022-1902(61)80148-6>
12g. Wynter C. I., Hill J., Bledsoe W.: J. Chem. Phys. 1969, 50, 3872. <https://doi.org/10.1063/1.1671642>
12h. Yagi Y., Popov A. I.: J. Phys. Chem. 1967, 71, 2439. <https://doi.org/10.1021/j100867a008>
12i. Popov A. I., Marshall J. C., Stute F. B., Person W. B.: J. Am. Chem. Soc. 1961, 83, 3586. <https://doi.org/10.1021/ja01478a011>
12j. Jander J., Maurer A.: Z. Naturforsch. B 1978, 33, 1446. <https://doi.org/10.1515/znb-1978-1215>
13. Tebbe K. F., Graefe-Kavoosian A.: Z. Naturforsch. B 1996, 51, 1007. <https://doi.org/10.1515/znb-1996-0716>
14a. Ranganathan A., Pedireddi V. R.: Tetrahedron Lett. 1998, 39, 1803. <https://doi.org/10.1016/S0040-4039(98)00092-6>
14b. Masciocchi N., Bergamo M., Sironi A.: Chem. Commun. 1998, 1347. <https://doi.org/10.1039/a803486i>
14c. Sarma J. A. R. P., Allen F. H., Hoy V. J., Howard J. A. K., Thaimattam R., Biradha K., Desiraju G. R.: Chem. Commun. 1997, 101. <https://doi.org/10.1039/a605044a>
14d. Weiss R., Schwab O., Hampel F.: Chem. Eur. J. 1999, 5, 968. <https://doi.org/10.1002/(SICI)1521-3765(19990301)5:3<968::AID-CHEM968>3.0.CO;2-L>
15. Ghassemzadeh M., Harms K., Dehnicke K.: Z. Naturforsch. B 1997, 52, 772. <https://doi.org/10.1515/znb-1997-0618>
16. Takakura T. in: Modern Fluoropolymers (J. Scheirs, Ed.), Chap. 29, p. 557. Wiley, New York 1997.
17a. Cardillo P., Corradi E., Lunghi A., Meille S. V., Messina M. T., Metrangolo P., Resnati G.: Tetrahedron 2000, 56, 5535. <https://doi.org/10.1016/S0040-4020(00)00476-2>
17b. Grebe J., Geiseler G., Harms K., Neumüller B., Dehnicke K.: Angew. Chem., Int. Ed. 1999, 38, 222. <https://doi.org/10.1002/(SICI)1521-3773(19990115)38:1/2<222::AID-ANIE222>3.0.CO;2-5>
18a. Smart B. E. in: Organofluorine Chemistry: Principles and Commercial Applications (R. E. Banks, B. E. Smart and J. C. Tatlow, Eds). Plenum Press, New York 1994.
18b. Hildebrand J. H., Cochran D. R. F.: J. Am. Chem. Soc. 1949, 71, 22. <https://doi.org/10.1021/ja01169a008>
18c. Dorset D. L.: Macromolecules 1990, 23, 894. <https://doi.org/10.1021/ma00205a034>
19. Améduri B., Boutevin B.: J. Fluorine Chem. 1999, 100, 97. <https://doi.org/10.1016/S0022-1139(99)00220-1>
20a. Valerio G., Raos G., Meille S. V., Metrangolo P., Resnati G.: J. Phys. Chem. A 2000, 104, 1617. <https://doi.org/10.1021/jp993415j>
20b. Walsh R. B., Padgett C. W., Metrangolo P., Resnati G., Hanks T. W., Pennington W. T.: Cryst. Growth Des. 2001, 1, 165. <https://doi.org/10.1021/cg005540m>
21. Messina M. T., Metrangolo P., Panzeri W., Ragg E., Resnati G.: Tetrahedron Lett. 1998, 39, 9069. <https://doi.org/10.1016/S0040-4039(98)01996-0>
22. Messina M. T., Metrangolo P., Navarrini W., Radice S., Resnati G., Zerbi G.: J. Mol. Struct. 2000, 524, 87. <https://doi.org/10.1016/S0022-2860(99)00445-7>
23. Foster R.: Organic Charge-Transfer Complexes, p. 100. Academic Press, London 1969.
24a. Bondi A.: J. Phys. Chem. 1964, 68, 441. <https://doi.org/10.1021/j100785a001>
24b. Pauling L.: The Nature of the Chemical Bond, 3rd ed. Cornell University Press, Ithaca 1960.
25. Padmanabhan K., Paul I. C., Curtin D. Y.: Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1990, 46, 88. <https://doi.org/10.1107/S0108270189005007>
26a. Messina M. T., Metrangolo P., Panzeri W., Pilati T., Resnati G.: Tetrahedron 2001, 57, 8543. <https://doi.org/10.1016/S0040-4020(01)00794-3>
26b. Corradi E., Meille S. V., Messina M. T., Metrangolo P., Resnati G.: Tetrahedron Lett. 1999, 40, 7519. <https://doi.org/10.1016/S0040-4039(99)01479-3>
26c. Amico V., Meille S. V., Corradi E., Messina M. T., Resnati G.: J. Am. Chem. Soc. 1998, 120, 8261. <https://doi.org/10.1021/ja9810686>
26d. Navarrini W., Metrangolo P., Pilati T., Resnati G.: New J. Chem. 2000, 24, 777. <https://doi.org/10.1039/b002247k>
27. Fontana F., Forni A., Metrangolo P., Panzeri W., Pilati T., Resnati G.: Supramol. Chem. 2002, 14, 47. <https://doi.org/10.1080/10610270290006565>
28a. Thummel R. P., Jahng Y.: J. Org. Chem. 1985, 50, 2407. <https://doi.org/10.1021/jo00214a001>
28b. Elsbernd H., Beattie J. K.: J. Inorg. Nucl. Chem. 1972, 34, 771. <https://doi.org/10.1016/0022-1902(72)80463-9>
28c. Elytle F., Petrosky L. M., Carlson L. R.: Anal. Chim. Acta 1971, 57, 239. <https://doi.org/10.1016/S0003-2670(01)95109-8>
28d. Fielding P. E., Le Fevre R. J. W.: J. Chem. Soc. 1951, 1811. <https://doi.org/10.1039/jr9510001811>
29. Bessel C. A., See R. F., Jameson D. L., Churchill M. R., Takeuchi K. J.: J. Chem. Soc., Dalton Trans. 1992, 3223. <https://doi.org/10.1039/dt9920003223>
30a. Armspach D., Constable E. C., Housecroft C. E., Neuburger M., Zehnder M.: New J. Chem. 1996, 20, 331.
30b. Constable E. C., Thompson A. M. W. C., Tocher D. A., Daniels M. A. M.: New J. Chem. 1992, 16, 855.
30c. Constable E. C., Khan F. K., Marquez V. E., Raithby P. R.: Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1992, 48, 932. <https://doi.org/10.1107/S0108270191012015>
31. Thalladi V. R., Weiss H. C., Bläser D., Boese R., Nangia A., Desiraju G. R.: J. Am. Chem. Soc. 1998, 120, 8702. <https://doi.org/10.1021/ja981198e>
32. CAUTION: Bis(2,2,2-trifluoroethyl) ether is a highly toxic and volatile substance. It is known to act as a CNS stimulant (Merck Index, 11th ed., p. 657).
33. SADABS. Bruker AXS Inc., Madison (WI) 1999.
34. Altomare A., Cascarano G., Giacovazzo G., Guagliardi A.: J. Appl. Crystallogr. 1994, 27, 43535.
35. Sheldrick G. M.: SHELX97. Program for the Refinement of Crystal Structures. University of Göttingen, Göttingen 1997.