Design, synthesis, and conformational dynamics of a gated molecular basket

Journal of the American Chemical Society
Veselin MaslakJovica D Badjić

Abstract

We have developed a synthesis and examined the conformational behavior and recognition properties of dynamic molecular containers 1-3. As follows from the 1H NMR dilution, diffusion NMR, and vapor pressure osmometry measurements, compound 1 has a low affinity for intermolecular aggregation and is mostly present in monomeric form in dilute chloroform solutions. Inspecting the O-H chemical shift resonances of 1, 3, and model compound 4 as a function of temperature afforded the deltadelta/deltaT coefficients of 17.0, 17.3, and 4.7 ppb K(-1), respectively. In combination with the results from variable temperature 1H NMR and IR measurements, the existence of conformers of 1 and 3 in equilibrium, each having a different extent of hydrogen bonding, was confirmed. Molecular mechanics calculations suggested 1a as the most favorable conformation, with three additional conformers, 1b, 1c, and 1d, populating local energy minima. Further optimization of each of the four conformers using semiempirical PM3 and ab initio (HF/6-31G) methods allowed a determination of their relative free energies and the corresponding Boltzmann population distributions which were heavily weighted toward 1a. A computed composite IR spectrum of a fraction-weighted...Continue Reading

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Citations

Apr 12, 2011·Accounts of Chemical Research·Fabrizio FabrisOttorino De Lucchi
Jun 10, 2010·Physical Chemistry Chemical Physics : PCCP·Yin-Feng WangChia-Chung Sun
Sep 13, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaoyong LuJovica D Badjić
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