Bis-thiourea macrocycles incorporating fused [n]polynorbornanes: binding of flexible versus rigid dicarboxylates

Johnstone, Mark D. and Pfeffer, Frederick M. 2014, Bis-thiourea macrocycles incorporating fused [n]polynorbornanes: binding of flexible versus rigid dicarboxylates, Supramolecular chemistry, vol. 26, no. 3-4, pp. 202-206.

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Title Bis-thiourea macrocycles incorporating fused [n]polynorbornanes: binding of flexible versus rigid dicarboxylates
Author(s) Johnstone, Mark D.
Pfeffer, Frederick M.
Journal name Supramolecular chemistry
Volume number 26
Issue number 3-4
Start page 202
End page 206
Total pages 5
Publisher Taylor & Francis
Place of publication London, England
Publication date 2014
ISSN 1061-0278
1029-0478
Keyword(s) Anion recognition
Macrocycle
Preorganisation
Thiourea
Summary Two macrocyclic bis-thiourea hosts 5 and 6 were constructed and their interactions with two dicarboxylates of similar size (pimelate = flexible and terephthalate = rigid) were evaluated using 1H NMR titration techniques. In contrast to previous work with thiourea functionalised [n]polynorbornanes (where a notable increase in H:G affinity was noted for the rigid guest), the new macrocyclic hosts, in particular host 6, bind pimelate more strongly than terephthalate (for 6 binding pimelate log Ka = 4.7, terephthalate log Ka = 3.7). A binding arrangement in which the flexible dicarboxylate is ‘perched’ above the macrocycle is proposed to justify these results.
Language eng
Field of Research 059999 Environmental Sciences not elsewhere classified
Socio Economic Objective 970105 Expanding Knowledge in the Environmental Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2013, Taylor & Francis
Persistent URL http://hdl.handle.net/10536/DRO/DU:30060879

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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