Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes
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Date
2016-04-04
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract
The syntheses and single crystal X-ray structure determinations of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(cyanomethoxy)calix[4]arene (partial-cone conformer), 5,11,17,23-tetra-tert-butyl-25,27-bis(diethylcarbamoylmethoxy)-26,28-bis(cyanomethoxy)calix[4]arene (cone and partial-cone conformers), 5,11,17,23-tetra-tert-butyl-25,26,27-tris(cyanomethoxy)-28-hydroxycalix[4]arene, and 5,11,17,23-tetra-tert-butyl-25-diethylcarbamoylmethoxy-26,27,28-tris(cyanomethoxy)calix[4]arene (cone conformer) are reported. The calixarenes are found to be conformationally mobile when heated in DMSO, favouring the partial-cone conformer at equilibrium. The tris-substituted cyanomethoxy derivative was found to assume the partial-cone conformation in the solid state. Attempts to convert nitrile groups to tetrazole moieties in derivatives containing both amide and nitrile groups were unsuccessful. © The Authors - CC-BY licence
Description
Keywords
Synthesis, Calixarenes, Heat, Nitroles, Tetrazoles, Solid state physics
Citation
D'Alessio, D., Krause-Heuer, A. M., Skelton, B. W., Fraser, B. H., Massi, M., & Ogden, M. I. (2016). Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy p-tert-butylcalix[4]arenes. RSC Advances, 6(43), 37006-37011. doi:10.1039/C6RA05865E