Abstract
Amidine-substituted allosteric receptors 2a and 2b for benzenediols were synthesized. Receptor 2a with five-membered amidines exhibited greater allostericity than the amide-substituted receptor 1, while 2b with six-membered amidines exhibited less allostericity. NMR titration experiments revealed that a significant enthalpic factor was involved in the allostericity of these receptors. X-ray and DFT optimized structures of 2a and 2b revealed that 2a adopted a coplanar conformation with π-conjugation between the amidines and the phenylene ring of the hydrindacene framework, resulting in high allostericity due to inactivation of the initial binding.
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