Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water

Chakraborty S, Grego AS, Garai S, Baranov M, Müller A, Weinstock IA (2019)
Journal of the American Chemical Society 141(23): 9170-9174.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Alcohols, with hydroxyl groups compositionally identical to water itself, are consummate hydrophiles, whose high solubilities preclude spontaneous self-assembly in water. Nevertheless, the solute-solvent interactions associated with their highly favorable solvation enthalpies impose substantial entropic costs, similar in magnitude to those that drive the hydrophobic assembly of alkanes. We now show that under nanoconfined conditions this normally dormant "hydrophobicity" can emerge as the driving force for alcohol encapsulation. Using a porous molecular capsule, the displacement of endohedrally coordinated formate ligands (HCO2-) by 1,2-hydroxyl-functionalized L-glycerate (L-gly, L-HOCH2(HO)CHCO2-) was investigated by van't Hoff analysis of variable-temperature H-1 NMR in D2O. At pD 5.8, L-gly uptake is enthalpically inhibited. Upon attenuation of this unfavorable change in enthalpy by cosequestration of protons within the alcoholic environment provided by encapsulated diol-functionalized ligands, -T Delta S degrees dominates over Delta H degrees, spontaneously filling the capsule to its host capacity of 24 L-gly ligands via an entropically driven hydrophobic response.
Erscheinungsjahr
2019
Zeitschriftentitel
Journal of the American Chemical Society
Band
141
Ausgabe
23
Seite(n)
9170-9174
ISSN
0002-7863
Page URI
https://pub.uni-bielefeld.de/record/2936953

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Chakraborty S, Grego AS, Garai S, Baranov M, Müller A, Weinstock IA. Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water. Journal of the American Chemical Society. 2019;141(23):9170-9174.
Chakraborty, S., Grego, A. S., Garai, S., Baranov, M., Müller, A., & Weinstock, I. A. (2019). Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water. Journal of the American Chemical Society, 141(23), 9170-9174. doi:10.1021/jacs.9b03542
Chakraborty, S., Grego, A. S., Garai, S., Baranov, M., Müller, A., and Weinstock, I. A. (2019). Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water. Journal of the American Chemical Society 141, 9170-9174.
Chakraborty, S., et al., 2019. Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water. Journal of the American Chemical Society, 141(23), p 9170-9174.
S. Chakraborty, et al., “Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water”, Journal of the American Chemical Society, vol. 141, 2019, pp. 9170-9174.
Chakraborty, S., Grego, A.S., Garai, S., Baranov, M., Müller, A., Weinstock, I.A.: Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water. Journal of the American Chemical Society. 141, 9170-9174 (2019).
Chakraborty, Sourav, Grego, Alina Shnaiderman, Garai, Somenath, Baranov, Mark, Müller, Achim, and Weinstock, Ira A. “Alcohols as Latent Hydrophobes: Entropically Driven Uptake of 1,2-Diol Functionalized Ligands by a Porous Capsule in Water”. Journal of the American Chemical Society 141.23 (2019): 9170-9174.

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