Synthesis, structure and conformational mobility of tetra-substituted cyanomethoxy: P-tert -butylcalix[4]arenes

D. D'Alessio, A.M. Krause-Heuer, Brian W. Skelton, B.H. Fraser, M. Massi, Mark I. Ogden

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


© The Royal Society of Chemistry 2016.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.
Original languageEnglish
Pages (from-to)37006-37011
Number of pages6
JournalRSC Advances
Issue number43
Publication statusPublished - 2016


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