Anion dependent molecular recognition of cations

Tetrahedron

Volumn 59, Issue 35, 2003, Pages 7067-7070

  Shivanyuk, Alexander ^a   Friese, Jan C ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Anion effects; Cavitands; Inclusion of cations; Supramolecular chemistry

Indexed keywords

ACETIC ACID; ANION; BENZIMIDAZOLE DERIVATIVE; CATION; CHLORIDE ION; PHOSPHONIUM DERIVATIVE; TETRYLAMMONIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; HYDROGEN BOND; ISOMER; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TIME;

EID: 0043160193     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00917-7     Document Type: Article

References (15)

1. For reviews and recent examples: (a) Rudkevich D.M., Rebek J. Jr. Eur. J. Org Chem. 1999;1991-2005 (b) Asfari Z., Böhmer V., Harrowfield J., Vicens J., Saadioui M. Calixarenes 2001. 2001;Kluwer Academic, Dordrecht, (c) Falabu D., Shivanyuk A., Nissinen M., Rissanen K. Org. Lett. 4:2002;3019-3022 (d) Gibb C.L., Stevens E.D., Gibb G.B. J. Am. Chem. Soc. 123:2001;5849-5850 (e) Atwood J.L., Szuma A. J. Am. Chem. Soc. 124:2002;10646-10647.
2. For reviews and recent examples: (a) Rudkevich D.M., Rebek J. Jr. Eur. J. Org Chem. 1999;1991-2005 (b) Asfari Z., Böhmer V., Harrowfield J., Vicens J., Saadioui M. Calixarenes 2001. 2001;Kluwer Academic, Dordrecht, (c) Falabu D., Shivanyuk A., Nissinen M., Rissanen K. Org. Lett. 4:2002;3019-3022 (d) Gibb C.L., Stevens E.D., Gibb G.B. J. Am. Chem. Soc. 123:2001;5849-5850 (e) Atwood J.L., Szuma A. J. Am. Chem. Soc. 124:2002;10646-10647.
3. For reviews and recent examples: (a) Rudkevich D.M., Rebek J. Jr. Eur. J. Org Chem. 1999;1991-2005 (b) Asfari Z., Böhmer V., Harrowfield J., Vicens J., Saadioui M. Calixarenes 2001. 2001;Kluwer Academic, Dordrecht, (c) Falabu D., Shivanyuk A., Nissinen M., Rissanen K. Org. Lett. 4:2002;3019-3022 (d) Gibb C.L., Stevens E.D., Gibb G.B. J. Am. Chem. Soc. 123:2001;5849-5850 (e) Atwood J.L., Szuma A. J. Am. Chem. Soc. 124:2002;10646-10647.
4. For reviews and recent examples: (a) Rudkevich D.M., Rebek J. Jr. Eur. J. Org Chem. 1999;1991-2005 (b) Asfari Z., Böhmer V., Harrowfield J., Vicens J., Saadioui M. Calixarenes 2001. 2001;Kluwer Academic, Dordrecht, (c) Falabu D., Shivanyuk A., Nissinen M., Rissanen K. Org. Lett. 4:2002;3019-3022 (d) Gibb C.L., Stevens E.D., Gibb G.B. J. Am. Chem. Soc. 123:2001;5849-5850 (e) Atwood J.L., Szuma A. J. Am. Chem. Soc. 124:2002;10646-10647.
5. For reviews and recent examples: (a) Rudkevich D.M., Rebek J. Jr. Eur. J. Org Chem. 1999;1991-2005 (b) Asfari Z., Böhmer V., Harrowfield J., Vicens J., Saadioui M. Calixarenes 2001. 2001;Kluwer Academic, Dordrecht, (c) Falabu D., Shivanyuk A., Nissinen M., Rissanen K. Org. Lett. 4:2002;3019-3022 (d) Gibb C.L., Stevens E.D., Gibb G.B. J. Am. Chem. Soc. 123:2001;5849-5850 (e) Atwood J.L., Szuma A. J. Am. Chem. Soc. 124:2002;10646-10647.
6. (a) Rudkevich D.M., Hilmersson G., Rebek J. Jr. J. Am. Chem. Soc. 120:1998;12216-12225.
7. (b) Ma S., Rudkevich D.M., Rebek J. Jr. Angew. Chem. Int. Ed. 38:1999;2600-2602.
8. (a) Haino T., Rudkevich D.M., Rebek J. Jr. J. Am. Chem. Soc. 121:1999;11253-11254.
9. (b) Haino T., Rudkevich D.M., Shivanyuk A., Rissanen K., Rebek J. Jr. Chem. Eur. J. 6:2000;3797-3805.
10. (c) Amrhein P., Shivanyuk A., Johnson D., Rebek J. Jr. J. Am. Chem. Soc. 124:2002;10349-10358.
11. Rafai Far A., Shivanyuk A., Rebek J. Jr. J. Am. Chem. Soc. 124:2002;2854-2855.
12. In apolar solvents cavitand 4 is vase shaped and forms hydrogen bonded dimeric capsules. See: (a) Heinz T., Rudkevich D.M., Rebek J. Jr. Angew. Chem. Int. Ed. Engl. 38:1999;1136-1139 (b) Heinz T., Rudkevich D.M., Rebek J. Jr. Nature. 394:1998;764-766.
13. In apolar solvents cavitand 4 is vase shaped and forms hydrogen bonded dimeric capsules. See: (a) Heinz T., Rudkevich D.M., Rebek J. Jr. Angew. Chem. Int. Ed. Engl. 38:1999;1136-1139 (b) Heinz T., Rudkevich D.M., Rebek J. Jr. Nature. 394:1998;764-766.
14. Compare to: Ballester P., Shivanyuk A., Rafai Far A., Rebek J. Jr. Am. Chem. Soc. 24:2002;14014-14016.
15. Hydrogen bonding between four halide anions and four secondary ammonium residues on the wider rim of resorcinarene enlarged the intramolecular cavity and resulted in anion dependent inclusion of alcohols: Shivanyuk A., Spaniol T.P., Rissanen K., Kolehmainen E., Böhmer V. Angew. Chem. Int. Ed. Engl. 39:2000;3497-3500.