The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Pyridinepropionic acid( cas:3724-19-4 ) is researched.Name: 3-Pyridinepropionic acid.Hunter, Christopher A.; Misuraca, Maria Cristina; Turega, Simon M. published the article 《Dissection of Complex Molecular Recognition Interfaces》 about this compound( cas:3724-19-4 ) in Journal of the American Chemical Society. Keywords: zinc porphyrin association constant pyridylcarboxylate pyridylphosphonate hydrogen bond. Let’s learn more about this compound (cas:3724-19-4).
The synthesis of a family of zinc porphyrins and pyridine ligands equipped with peripheral H-bonding functionality provided access to a wide range of closely related supramol. complexes featuring between zero and four intramol. H-bonds. An automated UV/visible titration system was used to characterize 120 different complexes, and these data were used to construct a large of number of different chem. double mutant cycles to quantify the intramol. H-bonding interactions. The results probe the quant. structure-activity relation that governs cooperativity in the assembly of complex mol. recognition interfaces. Specifically, variations in the chem. structures of the complexes have allowed the authors to change the supramol. architecture, conformational flexibility, geometric complementarity, the number and nature of the H-bond interactions, and the overall stability of the complex. The free energy contributions from individual H-bonds are additive, and there is remarkably little variation with architecture in the effective molarity for the formation of intramol. interactions. Intramol. H-bonds are not observed in complexes where they are geometrically impossible, but there are no cases where excellent geometric complementarity leads to very high affinities. Similarly, changes in conformational flexibility seem to have limited impact on the values of effective molarity (EM). The major variation that was found for all of the 48 intramol. interactions that were examined using double mutant cycles is that the values of EM for intramol. carboxylate ester-phenol H-bonds (200 mM) are an order of magnitude larger than those found for phosphonate diester-phenol H-bonds (30 mM). The corresponding intermol. phosphonate diester-phenol H-bonds are 2 orders of magnitude more stable than carboxylate ester-phenol H-bonds, and the large differences in EM may be due to some kind of compensation effect, where the stronger H-bond is harder to make, because it imposes tighter constraints on the geometry of the complex.
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Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem