American Chemical Society
ol070498a_si_004.pdf (5.66 MB)

Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH4+ Detected by Electrospray Ionization Mass Spectrometry

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journal contribution
posted on 2007-08-02, 00:00 authored by Anne Lélias-Vanderperre, Jean-Claude Chambron, Enrique Espinosa, Peran Terrier, Emmanuelle Leize-Wagner
Cation-π interactions play an important role in biology. The title compounds are C3-symmetric macrotricycles built from resorcinol, a π 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-π interactions.