Eight new macrocyclic polyether ligands containing the proton-ionizable triazole subcyclic unit have been prepared. Most of these compounds contain octyl, benzo or cyclohexano lipophilic groups. The unsubstituted triazolo-18-crown-6 (5) formed an unusual complex with silver ion. The crystal structure of this silver complex showed one crown complexed with one silver cation and two associated silver nitrate molecules. The new lipophilic triazolo-crowns are being tested as cation carriers for alkali and other metal cations in a bulk liquid membrane system.

References and Notes

2 J. S. Bradshaw, D. A. Chamberlin, P. E. Harrison, B. E. Wilson, G. Arena, N. K. Dalley, J. D. Lamb, R. M. Izatt, F. G. Morin and D. M. Grant, J. Org. Chem., 50, 3065 (1985).
10.1021/jo00217a010
CAS Google Scholar
3 J. S. Bradshaw, M. L. Colter, Y. Nakatsuji, N. O. Spencer, M. F. Brown, R. M. Izatt, G. Arena, P. K. Tse, B. E. Wilson, J. D. Lamb, N. K. Dalley, F. G. Morin and D. M. Grant, J. Org. Chem., 50, 4865 (1985).
10.1021/jo00217a010
CAS Google Scholar
4 J. S. Bradshaw, Y. Nakatsuji, P. Huszthy, B. E. Wilson, N. K. Dalley and R. M. Izatt, J. Heterocyclic Chem., 23, 353 (1986).
10.1002/jhet.5570230210
CAS Web of Science® Google Scholar
5 J. S. Bradshaw, R. B. Nielson, P. K. Tse, G. Arena, B. E. Wilson, N. K. Dalley, J. D. Lamb, J. J. Christensen and R. M. Izatt, J. Heterocyclic Chem., 23, 361 (1986).
10.1002/jhet.5570230211
CAS Web of Science® Google Scholar
6 R. M. Izatt, G. C. LindH, G. A. Clark, Y. Nakatsuji, J. S. Bradshaw, J. D. Lamb and J. J. Christensen, J. Membr. Sci., 31, 1 (1987).
10.1016/S0376-7388(00)81338-1
CAS Web of Science® Google Scholar
7 R. A. Bartsch, B. P. Czech, S. I. Kang, L. E. Stewart, W. Walkowiak, G. S. Heo and B. Son, J. Am. Chem. Soc., 107, 4997 (1985).
10.1021/ja00303a030
CAS Web of Science® Google Scholar
8 L. M. Dulyea, T. M. Fyles and D. M. Whitfield, Can. J. Chem., 62, 498 (1984).
10.1139/v84-083
CAS Web of Science® Google Scholar
9 C. Thomas, C. Sauterey, M. Castaing, C. M. Gary-Bobo, J. M. Lehn and P. Plumere, Biophys. Res. Commun., 116, 981 (1983).
10.1016/S0006-291X(83)80238-1
CAS PubMed Web of Science® Google Scholar
10 C. M. Browne, G. Fergeson, M. A. McKervey, D. L. Mulholland, T. O'Connor and M. Parvez, J. Am. Chem. Soc., 107, 2703 (1985).
10.1021/ja00295a024
CAS Web of Science® Google Scholar
11 See also R. M. Izatt, G. A. Clark, J. S. Bradshaw, J. D. Lamb and J. J. Christensen, Sep. Purif. Methods, 15, 21 (1986), for a review of protonionizable transport studies.
10.1080/03602548608068424
CAS Web of Science® Google Scholar
12 J. D. Lamb, R. M. Izatt, D. G. Garrick, J. S. Bradshaw and J. J. Christensen, J. Membr. Sci., 9, 33 (1981).
10.1016/S0376-7388(00)85119-4
CAS Web of Science® Google Scholar
13 J. S. Bradshaw, P. Huszthy, H. Koyama, S. G. Wood, S. A. Strobel, R. B. Davidson, R. M. Izatt, N. K. Dalley, J. D. Lamb and J. J. Christensen, J. Heterocyclic Chem., 23, 1837 (1986).
10.1002/jhet.5570230646
CAS Web of Science® Google Scholar
14 S. T. Jolley and J. S. Bradshaw, J. Org. Chem., 45, 3554 (1980).
10.1021/jo01306a003
CAS Web of Science® Google Scholar
15 G. E. Maas, J. S. Bradshaw, R. M. Izatt and J. J. Christensen, J. Org. Chem., 42, 3937 (1977).
10.1021/jo00444a032
CAS Web of Science® Google Scholar
16 G. M. Sheldrick, “ SHELXTL. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data”, University of Gottingen, Federal Republic of Germany, 4th revision, 1983.
Google Scholar
17 “ International Tables for X-ray Crystallography”, Vol 4, J. A. Ibers and W. C. Hamilton, Kynock Press, Birmingham, England, 1974, p 99.
Google Scholar

Citing Literature

Volume24, Issue4

July/August 1987

Pages 1085-1092

Proton-ionizable crown compounds. 13. Synthesis and structural studies of crown compounds containing the triazole subcyclic unit and lipophilic substituents^†

Abstract

References and Notes

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Proton-ionizable crown compounds. 13. Synthesis and structural studies of crown compounds containing the triazole subcyclic unit and lipophilic substituents†

Abstract

References and Notes

Citing Literature

References

Related

Information

Proton-ionizable crown compounds. 13. Synthesis and structural studies of crown compounds containing the triazole subcyclic unit and lipophilic substituents^†