Lower rim-upper rim hydrogen-bonded adducts of calix[4]arenes

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Abstract

An upper-rim-substituted calix[4]arene tetracarboxylic acid forms hydrogen-bonded duplexes with lower-rim-substituted tetra(4-pyridyl)- and tetra(3-pyridyl)calix[4]arenes in chloroform. The formation of these adducts was studied by extraction experiments. The association constants determined via1H NMR dilution experiments in CDCl3 are 7.6 × 103 and 1.3 × 103 M-1 for the 4-pyridyl and the 3-pyridyl derivative, respectively. IR studies in the solid state and in solution indicate that the interaction is based on hydrogen bonding and that the degree of proton transfer is negligible. VPO measurements support the formation of 1:1 adducts.
Original languageEnglish
Pages (from-to)4282-4288
JournalJournal of organic chemistry
Volume61
Issue number13
DOIs
Publication statusPublished - 1996

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