Molecular tweezers as synthetic receptors: Molecular recognition of neutral and cationic aromatic substrates. A comparison between the supramolecular structures in crystal and in solution

Journal of Physical Organic Chemistry

Volumn 13, Issue 10, 2000, Pages 604-611

  Klärner, Frank Gerrit ^a   Burkert, Ulrich ^a   Kamieth, Markus ^a   Boese, Roland ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

1H NMR spectroscopy; Molecular tweezers; Single crystal structure analysis; Supramolecular chemistry; Synthesis

Indexed keywords

EID: 0042286495     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-1395(200010)13:10<604::AID-POC271>3.0.CO;2-7     Document Type: Article

References (24)

1. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
2. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
3. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
4. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
5. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
6. Hunter CA. Chem. Soc: Rev. 1994; 23: 101-109; Adams H, Carver FJ, Hunter CA, Morales JC, Seward EM. Angew. Chem. 1996; 108: 1628-1631; Angew. Chem., Int. Ed. Engl. 1996; 35: 1542-1544; Kim E, Paliwal S, Wilcox CS. J. Am. Chem. Soc. 1998; 120: 11192-11193; Jorgensen WL, Severance DL. J. Am. Chem. Soc. 1990; 112: 4768-4774; Chipot C, Jaffe R, Maigret B. Pearlman DA, Kollman PA. J. Am. Chem. Soc. 1996; 118: 11217-11224.
7. Dougherty DA. Science 1996; 271: 163-168; Ma JC. Dougherty DA. Chem. Rev. 1997; 97: 1303-1324. and references cited therein.
8. Dougherty DA. Science 1996; 271: 163-168; Ma JC. Dougherty DA. Chem. Rev. 1997; 97: 1303-1324. and references cited therein.
9. Lehn J-M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim, 1995;; Diederich F. Cyclophanes. Royal Society of Chemistry: Cambridge, 1991;; Cram DJ. Container Molecules and Their Guests. Royal Society of Chemistry: Cambridge, 1994;; Vögtle F. Supramolekulare Chemie (2nd edn). Teubner: Stuttgart, 1992; Schneider H-J, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley-VCH: Weinheim, 1999.
10. Lehn J-M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim, 1995;; Diederich F. Cyclophanes. Royal Society of Chemistry: Cambridge, 1991;; Cram DJ. Container Molecules and Their Guests. Royal Society of Chemistry: Cambridge, 1994;; Vögtle F. Supramolekulare Chemie (2nd edn). Teubner: Stuttgart, 1992; Schneider H-J, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley-VCH: Weinheim, 1999.
11. Lehn J-M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim, 1995;; Diederich F. Cyclophanes. Royal Society of Chemistry: Cambridge, 1991;; Cram DJ. Container Molecules and Their Guests. Royal Society of Chemistry: Cambridge, 1994;; Vögtle F. Supramolekulare Chemie (2nd edn). Teubner: Stuttgart, 1992; Schneider H-J, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley-VCH: Weinheim, 1999.
12. Lehn J-M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim, 1995;; Diederich F. Cyclophanes. Royal Society of Chemistry: Cambridge, 1991;; Cram DJ. Container Molecules and Their Guests. Royal Society of Chemistry: Cambridge, 1994;; Vögtle F. Supramolekulare Chemie (2nd edn). Teubner: Stuttgart, 1992; Schneider H-J, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley-VCH: Weinheim, 1999.
13. Lehn J-M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim, 1995;; Diederich F. Cyclophanes. Royal Society of Chemistry: Cambridge, 1991;; Cram DJ. Container Molecules and Their Guests. Royal Society of Chemistry: Cambridge, 1994;; Vögtle F. Supramolekulare Chemie (2nd edn). Teubner: Stuttgart, 1992; Schneider H-J, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley-VCH: Weinheim, 1999.
14. Klärner F-G, Burkert U, Kamieth M, Boese R, Benet-Buchholz J. Chem. Eur. J. 1999; 5: 1700-1707.
15. Benkhoff J, Boese R, Klärner F-G. Liebigs Ann./Recl. 1997; 501-515.
16. Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U. Angew. Chem. 1996; 108: 1195-1198; Angew. Chem., Int. Ed. Engl. 1996; 35: 1130-1133.
17. Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U. Angew. Chem. 1996; 108: 1195-1198; Angew. Chem., Int. Ed. Engl. 1996; 35: 1130-1133.
18. Kamieth M, Burkert U, Corbin PS, Dell SJ, Zimmerman SC, Klärner F-G. Eur. J. Org. Chem. 1999; 2741-2749.
19. Hunter CA, Packer MJ. Chem. Eur. J. 1999; 5: 1891-1897.
20. Reichardt C. Solvents and Solvent Effects in Organic Chemistry (2nd edn). VCH: Weinheim, 1990.
21. Kamieth M, Klärner F-G, Diederich F. Angew. Chem. 1998; 110: 3497-3500; Angew. Chem., Int. Ed. Engl. 1998; 37: 3303-3306.
22. Kamieth M, Klärner F-G, Diederich F. Angew. Chem. 1998; 110: 3497-3500; Angew. Chem., Int. Ed. Engl. 1998; 37: 3303-3306.
23. Kamieth M, Klärner F-G. J. Prakt. Chem. 1999; 341: 245-251.
24. CRC Handbook of Chemistry and Physics (72nd edr), Lide DR, (ed). CRC Press: Boca Raton, FL, 1991.