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

Last Page

954

DOI

doi:10.3762/bjoc.15.91

Keywords

capsule, dimeric assemblies, halogen bonding, host–guest chemistry, resorcinarene salts, X-ray crystallography

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.

Creative Commons License

Creative Commons Attribution 4.0 License
This work is licensed under a Creative Commons Attribution 4.0 License.

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