Synthesis and structural properties of 5,17-bis (N-methyl-N-arylaminocarbonyl)calix[4]arenes. Directing the substituents toward the cavity by use of the cis-generating property of the N-methylaminocarbonyl linker

Frederik C Krebs, Mogens Larsen, Mikkel Jørgensen, Pernille Rose Jensen, Mia Bielecki, Kjeld Schaumburg

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A series of cone 5,17-bis(N-arylaminocarbonyl)calix[4]arenes were synthesized and N-methylated using an easy and high-yielding methylation procedure. The structures of the cone 5,17-bis(Nmethyl-N-arylaminocarbonyl)calix[4]arenes
were studied in solution by NMR spectroscopy and in the solid state by X-ray structural resolution. The use of the N-methylaminocarbonyl linker between
the calix[4]arene and the aromatic substituent was found to have a dominant influence on the molecular structure, forcing the substituent toward the cavity of the calix[4]arene regardless of the size of the substituent. The linker may be a very useful structure generator when considering the design of molecular receptors.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume63
Pages (from-to)9872-9879
ISSN0022-3263
DOIs
Publication statusPublished - 1998

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