The template synthesis and X-ray characterization of pyrrole-derived hexadentate uranyl(VI) Schiff-base macrocyclic complexes

Inorganica Chimica Acta

Volumn 246, Issue 1-2 SPEC. ISSUE, 1996, Pages 23-30

  Sessler, Jonathan L ^a   Mody, Tarak D ^b   Dulay, Maria T ^c   Espinoza, Roberto ^a   Lynch, Vincent ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b PHARMACYCLICS INC   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

Pyrrole derived; Schiff base complexes; Template condensation; Uranyl(VI) complexes

Indexed keywords

AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; CONDENSATION; DIHEDRAL ANGLE; FLUORINE COMPOUNDS; OXIDE MINERALS; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL); URANIUM DIOXIDE;

IRREVERSIBLE OXIDATION; O- PHENYLENEDIAMINE; PYRROLE-DERIVED; REVERSIBLE OXIDATION; SCHIFF BASE COMPLEXES; TEMPLATE CONDENSATION; URANYL(VI) COMPLEXES; X-RAY CHARACTERIZATION;

BORON COMPOUNDS;

EID: 0002862201     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/0020-1693(96)05046-3     Document Type: Article

References (39)

1. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
2. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
3. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
4. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
5. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
6. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
7. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
8. Uranyl complexes of Schiff base macrocyclic ligands, see: A.R. van Doom, M. Bos, S. Harkema, J. van Eerden, W, Verboom and D.N. Reinhoudt, J. Org. Chem., 56 (1991) 2371 and references therein; W. Nijenhuis, A.R. van Doorn, A.M. Reichwein, F. de Jong and D.N. Reinhoudt, J. Am. Chem. Soc., 113 (1991) 3607; R. Chandra, Synth. React. Inorg. Met.-Org. Chem., 20 (1990) 645 and references therein; U. Casellato, P. Guerriero, S. Tamburini, P.A. Vigato and R. Graziani, J. Chem. Soc., Dalton Trans., (1990) 1533; F. Benetollo, G. Bombieri, L. De Cola, A. Polo, D.L. Smailes and L.M. Vallarino, Inorg. Chem., 28 (1989) 3447; F.A. El-Saied, Inorg. Chim. Acta., 165 (1989) 147; F. Bullita, P. Guerriero, S. Tamburini and P.A. Vigato, J. Less Common Met., 153 (1989) 211; C.J. van Staveren, D.E. Fenton, D.N. Reinhoudt, J. van Eerden and S. Harkema, J. Am. Chem. Soc., 109 (1987) 3456.
9. For overviews of macrocyclic Schiff base complexes of lanthanides and actinides, see: V. Alexander, Chem. Rev., 95 (1995) 273; D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17 (1988) 69; G. Bombieri, Inorg. Chim. Acta, 139 (1987) 21; L.M. Vallarino, in, K.A. Gschneider, Jr. and L. Eyring (eds.), Handbook on the Physics and Chemistry of Rare Earths, Vol. 15, Ch. 4, Elsevier, Amsterdam, 1991.
10. For overviews of macrocyclic Schiff base complexes of lanthanides and actinides, see: V. Alexander, Chem. Rev., 95 (1995) 273; D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17 (1988) 69; G. Bombieri, Inorg. Chim. Acta, 139 (1987) 21; L.M. Vallarino, in, K.A. Gschneider, Jr. and L. Eyring (eds.), Handbook on the Physics and Chemistry of Rare Earths, Vol. 15, Ch. 4, Elsevier, Amsterdam, 1991.
11. For overviews of macrocyclic Schiff base complexes of lanthanides and actinides, see: V. Alexander, Chem. Rev., 95 (1995) 273; D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17 (1988) 69; G. Bombieri, Inorg. Chim. Acta, 139 (1987) 21; L.M. Vallarino, in, K.A. Gschneider, Jr. and L. Eyring (eds.), Handbook on the Physics and Chemistry of Rare Earths, Vol. 15, Ch. 4, Elsevier, Amsterdam, 1991.
12. For overviews of macrocyclic Schiff base complexes of lanthanides and actinides, see: V. Alexander, Chem. Rev., 95 (1995) 273; D.E. Fenton and P.A. Vigato, Chem. Soc. Rev., 17 (1988) 69; G. Bombieri, Inorg. Chim. Acta, 139 (1987) 21; L.M. Vallarino, in, K.A. Gschneider, Jr. and L. Eyring (eds.), Handbook on the Physics and Chemistry of Rare Earths, Vol. 15, Ch. 4, Elsevier, Amsterdam, 1991.
13. Uranyl(VI) superpthalocyanine, see: V.W. Day, T.J. Marks and W.A. Wachter, J. Am. Chem. Soc., 97 (1975) 4519; T.J. Marks and D.R. Stojakovic, J. Am. Chem. Soc., 100 (1978) 1695; E.A. Cuellar, D.R. Stojakovic and T.J. Marks, Inorg. Synth., 20 (1980) 97; E.A. Cuellar and T.J. Marks, Inorg. Chem., 20 (1981) 3766 ; T.J. Marks and D.R. Stojakovic, J. Chem. Soc., Chem. Commun., (1975) 28.
14. Uranyl(VI) superpthalocyanine, see: V.W. Day, T.J. Marks and W.A. Wachter, J. Am. Chem. Soc., 97 (1975) 4519; T.J. Marks and D.R. Stojakovic, J. Am. Chem. Soc., 100 (1978) 1695; E.A. Cuellar, D.R. Stojakovic and T.J. Marks, Inorg. Synth., 20 (1980) 97; E.A. Cuellar and T.J. Marks, Inorg. Chem., 20 (1981) 3766 ; T.J. Marks and D.R. Stojakovic, J. Chem. Soc., Chem. Commun., (1975) 28.
15. Uranyl(VI) superpthalocyanine, see: V.W. Day, T.J. Marks and W.A. Wachter, J. Am. Chem. Soc., 97 (1975) 4519; T.J. Marks and D.R. Stojakovic, J. Am. Chem. Soc., 100 (1978) 1695; E.A. Cuellar, D.R. Stojakovic and T.J. Marks, Inorg. Synth., 20 (1980) 97; E.A. Cuellar and T.J. Marks, Inorg. Chem., 20 (1981) 3766 ; T.J. Marks and D.R. Stojakovic, J. Chem. Soc., Chem. Commun., (1975) 28.
16. Uranyl(VI) superpthalocyanine, see: V.W. Day, T.J. Marks and W.A. Wachter, J. Am. Chem. Soc., 97 (1975) 4519; T.J. Marks and D.R. Stojakovic, J. Am. Chem. Soc., 100 (1978) 1695; E.A. Cuellar, D.R. Stojakovic and T.J. Marks, Inorg. Synth., 20 (1980) 97; E.A. Cuellar and T.J. Marks, Inorg. Chem., 20 (1981) 3766 ; T.J. Marks and D.R. Stojakovic, J. Chem. Soc., Chem. Commun., (1975) 28.
17. Uranyl(VI) superpthalocyanine, see: V.W. Day, T.J. Marks and W.A. Wachter, J. Am. Chem. Soc., 97 (1975) 4519; T.J. Marks and D.R. Stojakovic, J. Am. Chem. Soc., 100 (1978) 1695; E.A. Cuellar, D.R. Stojakovic and T.J. Marks, Inorg. Synth., 20 (1980) 97; E.A. Cuellar and T.J. Marks, Inorg. Chem., 20 (1981) 3766 ; T.J. Marks and D.R. Stojakovic, J. Chem. Soc., Chem. Commun., (1975) 28.
18. A.K. Burrell, G. Hemmi, V. Lynch and J.L. Sessler, J. Am. Chem. Soc., 113 (1991) 4690.
19. A.K. Burrell, M.J. Cyr, V. Lynch and J.L. Sessler, J. Chem. Soc., Chem. Commun., (1991) 1710.
20. J.L. Sessler, T.D. Mody and V. Lynch, Inorg. Chem., 31 (1992) 531; T.D. Mody, Ph.D. Dissertation, University of Texas at Austin, 1993.
21. J.L. Sessler, T.D. Mody and V. Lynch, Inorg. Chem., 31 (1992) 531; T.D. Mody, Ph.D. Dissertation, University of Texas at Austin, 1993.
22. G. Marangoni, S. Degetto, R. Graziani, G. Bombieri and E. Forsellini, J. Inorg. Nucl. Chem., 36 (1974) 1787; G. Paolucci, G. Marangoni, G. Bandoli and D.A. Clemente, J. Chem. Soc., Dalton Trans., (1980) 459; R. Graziani, U. Casellato, P.A. Vigato, S. Tamburini and M. Vidali, J. Chem. Soc., Dalton Trans., (1983) 697; N.W. Alcock, D.J. Flanders and D. Brown J. Chem. Soc., Dalton Trans., (1985) 1001; A. Cousson, J. Proust and E.N. Rizkalla, Acta Crystallogr. C., 47 (1991) 2065.
23. G. Marangoni, S. Degetto, R. Graziani, G. Bombieri and E. Forsellini, J. Inorg. Nucl. Chem., 36 (1974) 1787; G. Paolucci, G. Marangoni, G. Bandoli and D.A. Clemente, J. Chem. Soc., Dalton Trans., (1980) 459; R. Graziani, U. Casellato, P.A. Vigato, S. Tamburini and M. Vidali, J. Chem. Soc., Dalton Trans., (1983) 697; N.W. Alcock, D.J. Flanders and D. Brown J. Chem. Soc., Dalton Trans., (1985) 1001; A. Cousson, J. Proust and E.N. Rizkalla, Acta Crystallogr. C., 47 (1991) 2065.
24. G. Marangoni, S. Degetto, R. Graziani, G. Bombieri and E. Forsellini, J. Inorg. Nucl. Chem., 36 (1974) 1787; G. Paolucci, G. Marangoni, G. Bandoli and D.A. Clemente, J. Chem. Soc., Dalton Trans., (1980) 459; R. Graziani, U. Casellato, P.A. Vigato, S. Tamburini and M. Vidali, J. Chem. Soc., Dalton Trans., (1983) 697; N.W. Alcock, D.J. Flanders and D. Brown J. Chem. Soc., Dalton Trans., (1985) 1001; A. Cousson, J. Proust and E.N. Rizkalla, Acta Crystallogr. C., 47 (1991) 2065.
25. G. Marangoni, S. Degetto, R. Graziani, G. Bombieri and E. Forsellini, J. Inorg. Nucl. Chem., 36 (1974) 1787; G. Paolucci, G. Marangoni, G. Bandoli and D.A. Clemente, J. Chem. Soc., Dalton Trans., (1980) 459; R. Graziani, U. Casellato, P.A. Vigato, S. Tamburini and M. Vidali, J. Chem. Soc., Dalton Trans., (1983) 697; N.W. Alcock, D.J. Flanders and D. Brown J. Chem. Soc., Dalton Trans., (1985) 1001; A. Cousson, J. Proust and E.N. Rizkalla, Acta Crystallogr. C., 47 (1991) 2065.
26. G. Marangoni, S. Degetto, R. Graziani, G. Bombieri and E. Forsellini, J. Inorg. Nucl. Chem., 36 (1974) 1787; G. Paolucci, G. Marangoni, G. Bandoli and D.A. Clemente, J. Chem. Soc., Dalton Trans., (1980) 459; R. Graziani, U. Casellato, P.A. Vigato, S. Tamburini and M. Vidali, J. Chem. Soc., Dalton Trans., (1983) 697; N.W. Alcock, D.J. Flanders and D. Brown J. Chem. Soc., Dalton Trans., (1985) 1001; A. Cousson, J. Proust and E.N. Rizkalla, Acta Crystallogr. C., 47 (1991) 2065.
27. G.M. Sheldrick, SHELXTL-Plus, Siemens Analytical X-Ray Instruments Inc., Madison, WI, USA, 1987.
28. D.T. Cromer and J.B. Mann, Acta Crystallogr., A24 (1968) 321.
29. D.T. Cromer and D. Liberman, J. Chem. Phys., 53 (1970) 1891.
30. R.F. Stewart, E.R. Davidson and W.T. Simpson, J. Phys. Chem., 42 (1965) 3175.
31. International Tables for X-Ray Crystallography, Vol. IV, Kynoch Press, Birmingham, UK, 1974, p 55.
32. S.M. Gadol and R.E. Davis, Organometallics, 1 (1982) 1607.
33. The preparation of 3,4-diethylpyrrole-2,5-dicarbaldehyde, 4, has also been reported by E. Vogel, N. Jux, E. Rodriguez-Val, J. Lex and H, Schmicker, Angew. Chem. Int. Ed. Engl., 29 (1990) 1387, see also Ref. [6].
34. Well prior to this work, Fenton et al. prepared a series of macrocycles derived from alkyl-free pyrrole-2,5-dicarbaldehyde, and used these to chelate Cu(II) and other cations of the transition series, see; D.E. Fenton and R. Moody, J. Chem. Soc., Dalton Trans., (1987) 219; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss, C.O. Rodriguez de Barbarin and G. Jones, J. Chem. Soc., Dalton Trans., (1986) 693; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss and G. Jones, Inorg. Chim. Acta, 83 (1984) L79.
35. Well prior to this work, Fenton et al. prepared a series of macrocycles derived from alkyl-free pyrrole-2,5-dicarbaldehyde, and used these to chelate Cu(II) and other cations of the transition series, see; D.E. Fenton and R. Moody, J. Chem. Soc., Dalton Trans., (1987) 219; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss, C.O. Rodriguez de Barbarin and G. Jones, J. Chem. Soc., Dalton Trans., (1986) 693; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss and G. Jones, Inorg. Chim. Acta, 83 (1984) L79.
36. Well prior to this work, Fenton et al. prepared a series of macrocycles derived from alkyl-free pyrrole-2,5-dicarbaldehyde, and used these to chelate Cu(II) and other cations of the transition series, see; D.E. Fenton and R. Moody, J. Chem. Soc., Dalton Trans., (1987) 219; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss, C.O. Rodriguez de Barbarin and G. Jones, J. Chem. Soc., Dalton Trans., (1986) 693; H. Adams, N.A. Bailey, D.E. Fenton, S. Moss and G. Jones, Inorg. Chim. Acta, 83 (1984) L79.
37. A.J. Bard (ed.), Encyclopedia of Electrochemistry of the Elements. Organic Section; Vol. XV, Marcel Dekker, New York, 1984.
38. Any imine reductions could not be observed because reduction potentials greater than ca. -1.6 V versus Ag/AgCl are well outside the electrochemical range of the solvent (i.e. +1.8 V to -1.6 V versus Ag/AgCl), see also Ref. [18].
39. A.J. Bard, Electrochemical Methods Fundamentals and Applications, Wiley, New York, 1980.