Premium
Water‐Soluble Calixarene Hosts that Specifically Recognize the Trimethylammonium Group or the Benzene Ring of Aromatic Ammonium Cations: A Combined 1 H NMR, Calorimetric, and Molecular Mechanics Investigation
Author(s) -
Arena Giuseppe,
Casnati Alessandro,
Contino Annalinda,
Lombardo Gaetano G.,
Sciotto Domenico,
Ungaro Rocco
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990201)5:2<738::aid-chem738>3.0.co;2-6
Subject(s) - calixarene , chemistry , ring (chemistry) , ammonium , molecular mechanics , benzene , sulfonate , ion , aromaticity , stereochemistry , crystallography , medicinal chemistry , polymer chemistry , molecule , organic chemistry , sodium
A selective dual binding mode towards aromatic ammonium ions is shown by two water‐soluble calix[4]arene tetracarboxylate hosts 1 and 2 , fixed in the cone conformation. The presence of sulfonate groups at the upper rim ( 2 ) induces inclusion of the aromatic ring of trimethylanilinium ion into the apolar calixarene cavity, whereas receptor 1 specifically recognizes the polar trimethylammonium group of this guest. Intermediate behavior is observed in other cases.