Deprotonation of Large Calixarenes – Cation Binding and Conformations*
Jack M. Harrowfield A C , George A. Koutsantonis A , Mark I. Ogden A B D , Alexandre N. Sobolev A and Allan H. White A
+ Author Affiliations
- Author Affiliations
A School of Chemistry and Biochemistry M310, The University of Western Australia, 35 Stirling Highway, Perth, WA 6009, Australia.
B Department of Chemistry and Nanochemistry Research Institute, Curtin University, GPO Box U1987, Perth, WA 6845, Australia.
C Current address: Institut de Science et d'Ingénierie Supramoléculaires, Université de Strasbourg, 8 allée Gaspard Monge, 67083 Strasbourg, France.
D Corresponding author. Email: m.ogden@curtin.edu.au
Australian Journal of Chemistry 69(5) 546-554 https://doi.org/10.1071/CH15761
Submitted: 7 December 2015 Accepted: 19 January 2016 Published: 2 March 2016
Abstract
Single crystal X-ray studies of p-t-butylcalix[10]arene·2dmso·7H2O (1) and [NMe4][p-t-butylcalix[9]arene-H]·2dmso·H2O (2), provide new data on these large macrocycles and their conformations, that of 2 being the first where an encapsulated [NMe4]+ cation is present, while 1 contains the neutral ligand. Both were obtained as crystalline products of the reactions of the calixarenes with tetramethylammonium hydroxide after prolonged standing. The structure of [NEt4][calix[4]arene-H], in which the cation approaches inclusion in the shallow cone of the anion, is also defined and compared with various other alkylammonium derivatives of calixarenes as well as that of p-t-butylcalix[9]arene.
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