Macrotricycles featuring a pi-basic tetrahedral cavity: preference for NH4+ detected by electrospray ionization mass spectrometry.
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.
Lélias-Vanderperre
Anne
A
Université de Bourgogne, Laboratoire d'Ingénierie Moléculaire pour la Reconnaissance et la Séparation des Métaux et des Molécules (ICMUB, UMR CNRS n 5260), 9 avenue Alain Savary, BP 47870, 21078 Dijon, France.
Chambron
Jean-Claude
JC
Espinosa
Enrique
E
Terrier
Peran
P
Leize-Wagner
Emmanuelle
E
D018360:Crystallography, X-Ray; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011188:Potassium / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D047028:Macrocyclic Compounds; D000644:Quaternary Ammonium Compounds; D012118:Resorcinols; D011188:Potassium; C031389:resorcinol