European Journal of Organic Chemistry
10.1002/ejoc.201700106
COMMUNICATION
iodopryidine may induce a halogen bonding interaction between
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the guest and the host pyridine. Unfortunately, no indication
for such a behaviour or any encapsulation phenomena was
observed for 3-iodopryidine (entry 8). Interestingly, also 2-
hydroxypyridine does not seem to be a suitable guest for 13
[
[
[
3]
4]
5]
2
1
(
entry 9). For entries 5 to 9 in table 1 were no or only very minor
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signal shifts (0.03 ppm or less) in the presence of 13 compared
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guest functionalization and it’s functionalization pattern. This is
further supported by the fact that resorcinol (21) that offers
similar to 20 also a 1,3-difunctionalization is encapsulated by 13
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gives no clear indication for encapsulation. For comparison,
while the signals of 20 in the presence of 13 shift up to 0.87 ppm
compared to the free guest (signals c, d and e in Figure 1d and
e) the signals corresponding to catechol shift by less then 0.10
ppm. A full list of all encapsulation experiments and detailed
description can be found in the supporting information.
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Acknowledgements
M.O. thanks the sustainability scheme of Utrecht University for
funding. Johann Jastrezbski, Henk Kleijn and Arnoldus J. van
Schaik are acknowledged for technical support. The X-ray
diffractometer has been financed by the Netherlands
Organization for Scientific Research (NWO).
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Keywords: Hetero-Sequenced Cage • Dynamic Combinatorial
Chemistry • Cavity Design • Interior Functionalization • Arene
Encapsulation
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CCDC 1515608 contains the supplementary crystallographic data for this
paper. These data can be obtained free of charge from The Cambridge
Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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