X-ray structural studies on weak, non-covalent interactions in supramolecular compounds
Abstract
22 novel crystal structures of organic, supramolecular compounds and their analysis are reported. The structures present examples of a few of the most typical classes of compounds in supramolecular chemistry, i.e. crown ethers, cyclophanes, calix[4]arenes and resorcin[4]arenes. Crown ether structures (original publications I-IV; 14 structures) present an example of host-guest complexes in which hydrogen bonding interactions play a major role but in which other weak interactions also contribute to the complexation. Cyclophane structures incorporating bisphenol A units (publications V and VI; four structures) demonstrate the importance of the preorganisation and the suitable size of the cavity for complexation. The third class of potential, supramolecular macrocyclic host compounds, calix[4]arenes (publications VII and VIII; two structures), showed no molecular or clathrate inclusion of the solvent thus confirming the unsuitability of this type of calix[4]arenes for complexation. However, the crystal structures provided valuable information for the designing of further synthetic steps. The crystal structure of ethyl resorcin[4]arene cocrystallised with melamine (publication IX; two structures) revealed an exceptional guest-induced conformational change of the resorcinarene from crown to boat conformation. Special attention in all these studies has also been paid to the investigation of crystal packing and the weak intermolecular forces affecting it in addition to the sterical effects. As an introduction to the subject a short review of the literature will present the most typical weak interactions and the classes of macrocyclic, supramolecular hosts discussed in the experimental part.
Main Author
Format
Theses
Doctoral thesis
Published
2001
Series
ISBN
978-951-39-9908-7
The permanent address of the publication
https://urn.fi/URN:ISBN:978-951-39-9908-7Use this for linking
ISSN
0357-346X
Language
English
Published in
Research report / Department of Chemistry, University of Jyväskylä
Contains publications
- Artikkeli I: Nissinen, M., Rissanen, K., Kiviniemi, S., Sillanpää, A., & Lämsä, M. T. (1999). Polar Crystals with One-Dimensional Arrays from Achiral Components: Crystal Structures of 2:2 Complexes of Dibenzo-18-crown-6-imidazolium and pyrazolium Perchlorates. Chemical Communications, 1999(10), 897-898. DOI: 10.1039/A902014D
- Artikkeli II: Kiviniemi, S., Nissinen, M., Lämsä, M., Jalonen, J., Rissanen, K., & Pursiainen, J. (2000). Complexation of Planar, Organic, Five-membered Cations with Crown Ethers. New Journal of Chemistry, 24, 47-52. DOI: 10.1039/A907608E
- Artikkeli III: Nissinen, M., Rissanen, K., Kiviniemi, S., Kolli, T., Jalonen, J., & Pursiainen, J. (2001). Crown ether complexes of six-membered N-heteroaromatic cations. Journal of Incusion Phenomena and Macrocyclic Chemistry, 40, 153-159. DOI: 10.1023/a:1011176602813
- Artikkeli IV: Nissinen, M., Kiviniemi, S., Rissanen, K., & Pursiainen, J. (2000). Guest-driven dimer formation of dibenzo-18-crown-6. CrystEngComm, 2(18), 102-105. DOI: 10.1039/B004292G
- Artikkeli V: Nissinen, M., Cort, A. D., Amabile, S., Luigi, M., Rissanen, K. (2001). Bis-Phenol A Cyclophanes: Synthesis, Crystal Structures and Binding Studies. Journal of Inclusion Phemomena and Macrocyclic Chemistry, 39, 229-234. DOI: 10.1023/A:1011174213426
- Artikkeli VI: Nissinen, M., Rissanen, K., Cort, A. D., Amabile, D., Nocoletti, E., Mancinetti, L., & Mandolini, L. (2001). Polyether-Bridged Cyclophanes incorporating Bisphenol A Units as neutral receptors for Quats: Synthesis, Molecular Structure and Binding Properties. Journal of Physical Organic Chemistry, 14(7), 425-431. DOI: 10.1002/poc.380
- Artikkeli VII: Nissinen, M., Rissanen, K., Mogck, O., Parzuchowski, P., Rokicki, G., & Böhmer, V. (1998). Covalently Linked Multiple-Calixarene Systems. Tetrahedron, 54(34), 10053-68. DOI: 10.1016/S0040-4020(98)00594-8
- Artikkeli VIII: Nissinen, M., Rissanen, K., Böhmer, V., Parzuchowski, P., & Rokicki, G. (1999). 25,27-Dihydroxyethoxy-26,28-dipropoxy-tert-butylcalix[4]arene. Acta Crystallographica, C55, 104-106. DOI: 10.1107/S0108270198010221
- Artikkeli IX: Nissinen, M., Falábu, D., Wegelius, E., & Rissanen, K. (2000). Melamine induced conformational change of ethyl resorcinarene in solid state. CrystEngComm, 2(28), 151-153. DOI: 10.1039/B006193J
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