Strongly underestimated dispersion energy in cryptophanes and their complexes

Gebhard Haberhauer (), Sascha Woitschetzki and Heinz Bandmann
Additional contact information
Gebhard Haberhauer: Institut für Organische Chemie, Fakultät für Chemie, Universität Duisburg-Essen, Universitätsstrasse 7
Sascha Woitschetzki: Institut für Organische Chemie, Fakultät für Chemie, Universität Duisburg-Essen, Universitätsstrasse 7
Heinz Bandmann: Institut für Organische Chemie, Fakultät für Chemie, Universität Duisburg-Essen, Universitätsstrasse 7

Nature Communications, 2014, vol. 5, issue 1, 1-7

Abstract: Abstract Cryptophanes, composed of two bowl-shaped cyclotriveratrylene subunits linked by three aliphatic linker groups, are prototypal organic host molecules which bind reversibly neutral small guest compounds via London forces. The binding constants for these complexes are usually measured in tetrachloroethane and are in the range of 102–103 M−1. Here we show that tetrachloroethane is—in contrast to the scientific consensus—enclosed by the cryptophane-E cavity. By means of NMR spectroscopy we show that the binding constant for CHCl3@cryptophane-E is in larger solvents two orders of magnitudes higher than the one measured before. Ab initio calculations reveal that attractive dispersion energy is responsible for high binding constants and for the formation of imploded cryptophanes which seem to be more stable than cryptophanes with empty cavities.

Date: 2014
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms4542 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms4542

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/ncomms4542

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().