Organic Letters 2007-Aug
Macrotricycles featuring a pi-basic tetrahedral cavity: preference for NH4+ detected by electrospray ionization mass spectrometry.
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Abstract
Cation-pi interactions play an important role in biology. The title compounds are C3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.