Selective binding of cis-1,3,5-cyclohexane tricarboxylic acid vs its epimeric trans isomer by a tripodal amidopyridine receptor; crystal structures of the 1:1 complexes.
[figure: see text] A tripodal tris-amidopyridine receptor forms a 1:1 complex with trans-1,3,5-cyclohexane tricarboxylic acid that is 1 order of magnitude less stable than the one formed with the corresponding cis-triacid epimer. The X-ray crystal structures of the complexes have been determined, confirming the binding geometry derived from NMR data in solution and force-field calculations, and its geometrical features are used to explain the observed selectivity.
Ballester
P
P
Departament de Química, Universitat de les Illes Balears, 07071 Palma de Mallorca, Spain. pablo.ballester@uib.es
Capó
M
M
Costa
A
A
Deyà
P M
PM
Gomila
R
R
Decken
A
A
Deslongchamps
G
G
D018360:Crystallography, X-Ray; D003510:Cyclohexanes; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D014233:Tricarboxylic Acids / Q000737:chemistry*
D003510:Cyclohexanes; D011725:Pyridines; D014233:Tricarboxylic Acids