Synthesis and Characterization of a Brønsted Pair Functionalized Shape-Persistent Macrocycle
Publication date
2015-09-04
Authors
Vliegenthart, Annette B.
Welling, Frank A L
Roemelt, Michael
Klein Gebbink, R.J.M.
Otte, Matthias
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Article
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taverne
Abstract
The first shape-persistent macrocycle 1 offering a Brønsted pair functionalized interior is described. Via postcyclization transformation, this heterosequenced compound can be obtained from its corresponding ester 2. The macrocycles differ dramatically in their characteristics such as solubility and appearance. Theoretical investigations suggest that those contrasts might originate from conformational changes due to the formation of a strong O-H-N hydrogen bond in 1.
Keywords
Taverne, Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Citation
Vliegenthart, A B, Welling, F A L, Roemelt, M, Klein Gebbink, R J M & Otte, M 2015, 'Synthesis and Characterization of a Brønsted Pair Functionalized Shape-Persistent Macrocycle', Organic Letters, vol. 17, no. 17, pp. 4172-4175. https://doi.org/10.1021/acs.orglett.5b01931