Guest-controlled formation of a hydrogen-bonded molecular capsule

Angewandte Chemie - International Edition

Volumn 38, Issue 19, 1999, Pages 2906-2909

  Shivanyuk, Alexander ^a   Paulus, Erich F ^b   Böhmer, Volker ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b SANOFI   (France)

Author keywords

Charge transfer; Host guest chemistry; Hydrogen bonds; Inclusion compounds; Supramolecular chemistry

Indexed keywords

HYDROXYL GROUP; PHENOL DERIVATIVE;

ARTICLE; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0033523609     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991004)38:19<2906::AID-ANIE2906>3.0.CO;2-F     Document Type: Article

References (16)

1. M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668.
2. R. G. Chapman, J. C. Sherman, Tetrahedron 1997, 53, 15911-15945.
3. A. Shivanyuk, E. F. Paulus, V. Böhmer, W. Vogt, J. Org. Chem. 1998, 63, 6448-6449.
4. 2v-symmetrical boat conformations).
5. See for example : M. Lämsä, J. Pursiainen, K. Rissanen, J. Huuskonen, Acta. Chem. Scand. 1998, 52, 563-570.
6. 1H NMR spectroscopy shows that complexation with tropylium rigidifies the conformation of 1a.
7. [5]
8. - was carried out for 6-8 h assisted by mechanical stirring.
9. a) R. Meuisner, X. Garcias, S. Mecozzi, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 77-85;
10. b) N. Branda, R. M. Grotzfeld, C. Valdes, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85-88;
11. c) O. Mogck, M. Pons, V. Böhmer, W. Vogt, J. Am. Chem. Soc. 1997, 119, 5706-5712.
12. The degree of dimerization of tetrahydroxy cavitands could be controlled by the amount of base used for the deprotonation of the hydroxy groups to form the dianion, while an appropriate space-filling guest (pyrazine) was available in excess: R. G. Chapman, G. Olovsson, J. Trotter, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 6252-6260.
13. A signal for the free tropylium cation is not observed.
14. -.
15. c c = 0.006 Å. Crystallographic data of this structure (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-119100. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
16. The reference plane of 1 is defined by the four bridging methin carbon atoms.