Bis(m-phenylene)-32-crown-10-based cryptands, powerful hosts for paraquat derivatives

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3231-3241

  Huang, Feihe ^a   Switek, Karen A ^a,b   Zakharov, Lev N ^c,d   Fronczek, Frank R ^e   Slebodnick, Carla ^a   Lam, Matthew ^c   Golen, James A ^f   Bryant, William S ^a,g   Mason, Philip E ^a,h   Rheingold, Arnold L ^c,d   Ashraf Khorassani, Mehdi ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b University of Minnesota   (United States)

^c UNIVERSITY OF DELAWARE   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e LOUISIANA STATE UNIVERSITY   (United States)

^f UNIVERSITY OF MASSACHUSETTS DARTMOUTH   (United States)

^g IMERYS MINERALS LTD   (United Kingdom)

^h Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; BINDING ENERGY; COMPLEXATION; DERIVATIVES; HYDROGEN; MASS SPECTROMETERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY ANALYSIS;

CRPTANDS; DIESTERS; GUEST-HOSTS REACTIONS; PARAQUATS;

CROWN ETHERS;

BIS(1,3,5 PHENYLENE)DI(1',4',7',10',13' PENTAOXATRIDECYL) 1'4' DI(METHYLENEOXY)BENZENE; BIS(1,3,5 PHENYLENE)DI(1',4',7',10',13' PENTAOXATRIDECYL) 2'6' DI(METHYLENEOXYCARBONYL)PYRIDINE; BIS(1,3,5 PHENYLENE)DI(1',4',7',10',13' PENTAOXATRIDECYL) 2'6' DIOXYMETHYLENEPYRIDINE; BIS(1,3,5 PHENYLENE)DI(1',4',7',10',13' PENTAOXATRIDECYL) 3'6' DI(METHYLENEOXY)BENZYL ALCOHOL; PARAQUAT; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL STRUCTURE; COMPLEX FORMATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; THERMODYNAMICS; X RAY ANALYSIS;

CRYSTALLOGRAPHY, X-RAY; ETHERS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PARAQUAT; SCHIFF BASES;

EID: 20244384562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050187i     Document Type: Article

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19. (f) Reviews: Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Harada, A. Acta Polym. 1998, 49, 3-17. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1664. Molecular Catenanes and Knots; Sauvage, J.-P., Dietrich-Bucheker, C., Eds.; Wiley: New York, 1999. Mahan, E.; Gibson, H. W. In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Kluwer Publishers: Dordrecht, 2000; pp 415-560. Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200-202, 5-52. Panova, I. G.; Topchieva, I. N. Russ. Chem. Rev. 2001, 70, 23-44.
20. (f) Reviews: Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Harada, A. Acta Polym. 1998, 49, 3-17. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1664. Molecular Catenanes and Knots; Sauvage, J.-P., Dietrich-Bucheker, C., Eds.; Wiley: New York, 1999. Mahan, E.; Gibson, H. W. In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Kluwer Publishers: Dordrecht, 2000; pp 415-560. Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200-202, 5-52. Panova, I. G.; Topchieva, I. N. Russ. Chem. Rev. 2001, 70, 23-44.
21. (f) Reviews: Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Harada, A. Acta Polym. 1998, 49, 3-17. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1664. Molecular Catenanes and Knots; Sauvage, J.-P., Dietrich-Bucheker, C., Eds.; Wiley: New York, 1999. Mahan, E.; Gibson, H. W. In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Kluwer Publishers: Dordrecht, 2000; pp 415-560. Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200-202, 5-52. Panova, I. G.; Topchieva, I. N. Russ. Chem. Rev. 2001, 70, 23-44.
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29. The only other bicyclic hosts that have been used for pseudorotaxane/rotaxane syntheses are the glycouril-crown etherporphyrin systems: (b) Rowan, A. E.; M. P. P.; K. W. Aarts,; Koutstaal, M. Chem. Commun. 1998, 611-612. (c) Gunter, M. J.; Jeynes, T. P.; Johnston, M. R.; Turner, P.; Chen, Z. J. Chem. Soc., Perkin Trans. 1 1998, 1945-1957. (d) Elemans, J. A. A. W.; Claase, M. B.; Aarts, P. P. M.; Rowan, A. E.; Schenning, A. P. H. J.; Nolte, R. J. M. J. Org. Chem. 1999, 64, 7009-7016.
30. The only other bicyclic hosts that have been used for pseudorotaxane/rotaxane syntheses are the glycouril-crown etherporphyrin systems: (b) Rowan, A. E.; M. P. P.; K. W. Aarts,; Koutstaal, M. Chem. Commun. 1998, 611-612. (c) Gunter, M. J.; Jeynes, T. P.; Johnston, M. R.; Turner, P.; Chen, Z. J. Chem. Soc., Perkin Trans. 1 1998, 1945-1957. (d) Elemans, J. A. A. W.; Claase, M. B.; Aarts, P. P. M.; Rowan, A. E.; Schenning, A. P. H. J.; Nolte, R. J. M. J. Org. Chem. 1999, 64, 7009-7016.
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48. 6 counterions, one as the anion and the other as neutral, is commonly observed in the positive ion mass spectra of low molar mass paraquat-based complexes. For relevant references, see: Amabilino, D. B.; Anelli, P.-L.; Ashton, P. R.; Brown, G. R.; Cordova, E.; Godinez, L. A.; Hayes, W.; Kaifer, A. E.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Am. Chem, Soc. 1995, 117, 11142-11170. Lukyanenko, N. G.; Kirichenko, T. I.; Lyapunov, A. Y.; Mazepa, A. V.; Simonov, Y. A.; Fonari, M. S.; Botoshansky, M. M. Chem. Eur. J. 2005, 11, 262-270.
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