Organobismuth(V) complexes containing bifunctional ligands: hydrogen-bonded extended structures and stereoselectivity

Abstract

New bismuth(V) complexes with the general formula of Bi^VR₃(O₂CR′)₂ have been synthesized by the reaction of BiR₃Cl₂ with Ag(O₂CR′), where R is an aromatic ligand and R′ a substituent containing a hydroxyl group. The role of these new bismuth(V) complexes as building blocks to form hydrogen-bonded extended structures in the solid has been examined by single-crystal X-ray diffraction analyses. The bismuth atoms in these compounds adopt distorted trigonal-bipyramidal geometries. The hydrogen-bonding pattern and the extended structure displayed have been found to be highly dependent on the R and the R′ groups. Unusual hydrogen-bonded extended structures such as double strands and double layers have been observed. In an attempt to obtain chiral helical extended structures, the reactions of BiR₃Cl₂ with several silver salts, Ag(O₂CR*), where R* contains one chiral centre and a hydroxyl group, were examined. The bismuth(V) centre shows an unusual stereoselectivity towards the chiral ligand R*CO₂^-. When a racemic mixture of Ag(O₂CR*) was used only the enantiomers (R,R)- and (S,S)-BiR₃(O₂CR*)₂ were obtained.

References

1. J.-M. Lehn, Angew. Chem., Int,. Ed. Engl., 1990, 29, 1304; D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95, 2229; C. M. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 1995, 34, 1696; G. D. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, New York, 1989; Transition Metals in Supramolecular Chemistry, eds. L. Fabbrizzi and A. Poggi, Kluwer, Dordrecht, 1994; C. B. Aakeröy and K. R. Seddon, Chem. Soc. Rev., 1993, 397; C. Fouquey, J. M. Lehn and A. M. Levelut, Adv. Mater., 1990, 2, 254; Topics in Current Chemistry, Supermolecular Chemistry II: Host Design and Molecular Recognition, ed. E. Weber, Springer, Berlin, 1995.
2. J. P. Mathias, E. E. Simanek, J. A. Zerkowski, C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 1994, 116, 4316; J. P. Mathias, E. E. Simanek and G. M. Whitesides, J. Am. Chem. Soc., 1994, 116, 4326; K. E. Schwiebert, D. N. Chin, J. C. MacDonald and G. M. Whitesides, J. Am. Chem. Soc., 1996, 118, 4018; D. S. Reddy, Y. E. Ovchinnikov, O. V. Shishkin, Y. T. Struchkov and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4085; D. S. Reddy, D. C. Craig and G. R. Desiraju, J. Am. Chem. Soc., 1996, 118, 4090.
3. J. E. Huheey, E. A. Keiter and R. L. Keiter, Inorganic Chemistry, Principles of Structure and Reactivity, Harper Collins College Publisher, 4th edn., New York, 1993.
4. S. Wang, K. D. L. Smith, Z. Pang and M. Wagner, J. Chem. Soc., Chem. Commun., 1992, 1594; S. Wang, S. J. Trepanier, J. C. Zheng, Z. Pang and M. J. Wagner, Inorg. Chem., 1992, 31, 2118.
5. M. Zaworotko, Chem. Soc. Rev., 1994, 283; S. B. Copp, S. Subramanian and M. J. Zaworotko, Angew. Chem., Int. Ed. Engl., 1993, 32, 706; S. R. Breeze and S. Wang, Inorg. Chem., 1993, 32, 5981.
6. C. J. Brinker, D. E. Clark and D. R. Ulrich, Mater. Res. Soc. Symp. Proc., 1988, 121; W. A. Hermann, E. Herdtweck and L. Pajdla, Inorg. Chem., 1991, 30, 2579; Metal-based Anti-tumour Drugs, ed. M. F. Gielen, Freund Publishing House, London, 1988; D. H. R. Barton, B. Charpiot, E. T. H. Dau, W. B. Motherwell and C. Pascard, Helv. Chim. Acta, 1984, 67, 586; E. Asato, K. Katsura, M. Mikuriya, T. Fujii and J. Reedijk, Inorg. Chem., 1993, 32, 5322.
7. (a) L. D. Freedman and G. O. Doak, Chem. Rev., 1982, 82, 15; (b) J. L. Wardell, in Comprehensive Organometallic Chemistry, eds. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, p. 681; (c) A. Hassan, S. R. Breeze, S. Courtenay, C. Deslippe and S. Wang, Organometallics, 1996, 15, 5613.
8. H. Gilman and H. L. Yablunky, J. Am. Chem. Soc., 1941, 63, 207; J.-M. Keck and G. Klar, Z. Naturforsch., Teil B, 1972, 27, 591.
9. (a) TEXSAN, Crystal Structure Analysis Package, Molecular Structure Corporation, Houston, TX, 1985 and 1992; (b) SHELX-TL, Version 5, Siemens Industrial Automation, Inc., Madison, WI.
10. D. T. Cromer and J. T. Waber, International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1974, vol. 4, table 2-2A.
11. (a) G. Ferguson, B. Kaitner, C. Glidewell and S. Smith, J. Organomet. Chem., 1991, 419, 283; (b) A. Schmuck, J. Buschman, J. Fuchs and K. Seppelt, Angew. Chem., Int. Ed. Engl., 1987, 26, 1180; (c) M. Domagala, H. Preut and F. Huber, Acta Crystallogr., Sect. C, 1988, 44, 830; (d) S. Wallenhauer and K. Seppelt, Inorg. Chem., 1995, 34, 116; (e) J. Bordner and L. D. Freedman, Phosphorus, 1973, 3, 33; (f) S. Wallenhauer and K. Seppelt, Angew. Chem., Int. Ed. Engl., 1994, 33, 976; (g) T. B. Brill and G. G. Long, Inorg. Chem., 1970, 9, 1980; (h) F. C. March and G. Ferguson, J. Chem. Soc., Dalton Trans., 1975, 1291.
12. C. K. Johnson, ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
13. S. R. Breeze and S. Wang, Angew. Chem., Int. Ed. Engl., 1993, 32, 589; S. R. Breeze, L. Chen and S. Wang, J. Chem. Soc., Dalton Trans., 1994, 2545.
14. W. C. Hamilton and J. A. Ibers, Hydrogen Bonding in Solids, W. A. Benjamin, New York, 1968; S. N. Vinpgradov and R. H. Linnell, Hydrogen Bonding, Van Nostrand-Reinhold, New York, 1971.
15. A. L. Lehninger, Principles of Biochemistry, Worth Publishers, New York, 1982; G. A. Jeffery and W. Saenger, Hydrogen Bonding in Biological Structures, Springer, New York, 1991.
16. (a) T. Suzuki, H. Kotsuki, K. Isobe, N. Moriya, Y. Nakagawa and M. Ochi, Inorg. Chem., 1995, 34, 530; (b) T. Kawamoto, O. Prakash, R. Ostrander, A. L. Rheingold and A. S. Borovik, Inorg. Chem., 1995, 34, 4294; (c) A. M. Gilbert, T. J. Katz, W. E. Geiger, M. P. Robben and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 3199; (d) T. Kawamoto, B. S. Hammes, B. Haggerty, G. P. A. Yap, A. L. Rheingold and A. S. Borovik, J. Am. Chem. Soc., 1996, 118, 285.
17. Liquid Crystals, The Fourth State of Matter, ed. F. D. Saeva, Marcel Dekker, New York, 1979; S. Chandrasekhar, Liquid Crystals, Cambridge University Press, Cambridge, 1977.
18. J. March, Advanced Organic Chemistry, Wiley, 3rd edn., New York, 1985, pp. 107–109 and refs. Therein; H. Hiemstra and H. Wynberg, Tetrahedron Lett., 1977, 2183.