Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.
The straightforward syntheses of C3v symmetrical calix[6]trisureas and -thiourea have been achieved. NMR studies have shown that these flexible compounds possess a major cone conformation. While these neutral hosts can strongly bind anions such as AcO(-) or HSO4(-) through induced fit processes, they can also behave as unique heteroditopic receptors for organic ion pairs with a remarkable positive cooperativity in the complexation process, the anion acting as an allosteric effector.
Hamon
Mélanie
M
URCOM, Université du Havre, FST, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France.
Ménand
Mickaël
M
Le Gac
Stéphane
S
Luhmer
Michel
M
Dalla
Vincent
V
Jabin
Ivan
I
D001665:Binding Sites; D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D007477:Ions; D010636:Phenols; C476540:calix(6)arene; D047250:Calixarenes; D014508:Urea; D013890:Thiourea