Shape-complementarity in the recognition of tricarboxylic acids by a [3+3] polyazacyclophane receptor.
[structure: see text] The interaction of a macrocycle containing three trans-(1R,2R)-diaminocyclohexane units connected by p-xylene spacers with the isomers 1,3,5-benzenetricarboxylic (1,3,5-BTC), 1,2,4-benzenetricarboxylic (1,2,4-BTC), and 1,2,3-benzenetricarboxylic (1,2,3-BTC) acids and their relevant anions is studied by means of potentiometric and NMR analysis. The interaction is highest for the isomer 1,3,5-BTC, which perfectly fits within the macrocyclic cavity of the host species. The studies have been extended to the triacid 1,3,5-benzenetriacetic observing in this case the effect of a size mismatch between host and guest species.
Hodacová
Jana
J
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 166 10 Prague 6, Czech Republic.
Chadim
Martin
M
Závada
Jirí
J
Aguilar
Juan
J
García-España
Enrique
E
Luis
Santiago V
SV
Miravet
Juan F
JF
D001667:Binding, Competitive; D003514:Cyclohexylamines / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D014233:Tricarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*
D003514:Cyclohexylamines; D014233:Tricarboxylic Acids; C030435:1,2-cyclohexanediamine