Author ORCID Identifier
https://orcid.org/0000-0002-3091-6795 : Fangfang Pan
https://orcid.org/0000-0001-8200-1602 : Mohadeseh Dashti
https://orcid.org/0000-0002-8723-930X : Michael R. Reynolds
https://orcid.org/0000-0002-7282-8419 : Kari Rissanen
https://orcid.org/0000-0002-4780-4968 : John F. Trant
https://orcid.org/0000-0003-3935-1812 : Ngong Kodiah Beyeh
Document Type
Article
Publication Date
4-18-2019
Publication Title
Beilstein Journal of Organic Chemistry
Volume
15
First Page
947
Keywords
capsule, dimeric assemblies, halogen bonding, host–guest chemistry, resorcinarene salts, X-ray crystallography
Last Page
954
Abstract
Single crystal X-ray structures of halogen-bonded assemblies formed between host N-hexylammonium resorcinarene bromide (1) or N-cyclohexylammonium resorcinarene chloride (2), and 1,4-diiodooctafluorobutane and accompanying small solvent guests (meth- anol, acetonitrile and water) are presented. The guests’ inclusion affects the geometry of the cavity of the receptors 1 and 2, while the divalent halogen bond donor 1,4-diiodooctafluorobutane determines the overall nature of the halogen bond assembly. The crystal lattice of 1 contains two structurally different dimeric assemblies A and B, formally resulting in the mixture of a capsular dimer and a dimeric pseudo-capsule. 1H and 19F NMR analyses supports the existence of these halogen-bonded complexes and en- hanced guest inclusion in solution.
DOI
doi:10.3762/bjoc.15.91
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recommended Citation
Pan, Fangfang; Dashti, Mohadeseh; Reynolds, Michael R.; Rissanen, Kari; Trant, John F.; and Beyeh, Ngong Kodiah. (2019). Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests. Beilstein Journal of Organic Chemistry, 15, 947-954.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/139