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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2016

Polar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules

Résumé

Aromatic oligoamide sequences able to fold into single helical capsules were functionalized with two types of side chains to make them be soluble in various solvents such as chloroform, methanol or water and their propensity to recognize tartaric acid was evaluated. Binding affinities to tartaric acid and binding thermodynamics in the different media were investigated by variable temperature 1 H NMR and ITC experiments, the two methods giving consistent results. We show that tartaric acid binding mainly rests on enthalpically favourable polar interactions that were found to be sufficiently strong to be effective in presence of a polar aprotic solvent (DMSO) and even in pure methanol. Binding in water was very low. The stronger binding interactions were found to be more susceptible to the effect of competitive solvents and to be compensated by unfavourable entropic effects. Thus, the best host in less polar medium eventually was found to be the worst host in protic solvents. An interesting case of entropically driven binding was evidenced in methanol.

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Chimie
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Dates et versions

hal-01509472 , version 1 (19-04-2017)

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Citer

Nagula Chandramouli, Mohammed Farrag El-Behairy, Guillaume Lautrette, Yann Ferrand, Ivan Huc. Polar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules. Organic & Biomolecular Chemistry, 2016, 14 (8), pp.2466-2472. ⟨10.1039/c5ob02641e⟩. ⟨hal-01509472⟩

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