| FIALA, Tomáš, Kristína SLEZIAKOVÁ, Kamil MARŠÁLEK, Karolina SALVADORI and Vladimír ŠINDELÁŘ. Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents. Journal of Organic Chemistry. WASHINGTON: AMER CHEMICAL SOC, 2018, vol. 83, No 4, p. 1903-1912. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.7b02846. |
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@article{1419371,
author = {Fiala, Tomáš and Sleziaková, Kristína and Maršálek, Kamil and Salvadori, Karolina and Šindelář, Vladimír},
article_location = {WASHINGTON},
article_number = {4},
doi = {http://dx.doi.org/10.1021/acs.joc.7b02846},
keywords = {SOLVATION ENERGY RELATIONSHIPS; ANION-BINDING; LIQUID CHLOROFORM; SUPRAMOLECULAR COMPLEXES; MOLECULAR-DYNAMICS; HIGH-AFFINITY; RECOGNITION; IONS; SUBSTITUTION; RECEPTOR},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.7b02846},
volume = {83},
year = {2018}
}
TY - JOUR
ID - 1419371
AU - Fiala, Tomáš - Sleziaková, Kristína - Maršálek, Kamil - Salvadori, Karolina - Šindelář, Vladimír
PY - 2018
TI - Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents
JF - Journal of Organic Chemistry
VL - 83
IS - 4
SP - 1903-1912
EP - 1903-1912
PB - AMER CHEMICAL SOC
SN - 00223263
KW - SOLVATION ENERGY RELATIONSHIPS
KW - ANION-BINDING
KW - LIQUID CHLOROFORM
KW - SUPRAMOLECULAR COMPLEXES
KW - MOLECULAR-DYNAMICS
KW - HIGH-AFFINITY
KW - RECOGNITION
KW - IONS
KW - SUBSTITUTION
KW - RECEPTOR
UR - https://pubs.acs.org/doi/10.1021/acs.joc.7b02846
L2 - https://pubs.acs.org/doi/10.1021/acs.joc.7b02846
N2 - Driving forces of anion binding in water in contrast to nonpolar environments are of high interest because of their relevance to biology and medicine. Here we report a neutral bambusuril macrocycle (1), soluble in both water and nonpolar solvents due to decoration with 12 polyethylene glycol-based substituents. The new bambusuril has the highest affinity for I- in pure water ever reported for a synthetic macrocycle relying on hydrogen bonding interactions rather than metal coordination or Coulombic forces. Isothermal titration calorimetry (ITC) experiments in nine different solvents, ranging from polar water to nonpolar carbon tetrachloride, provided insight into the forces responsible for halide binding by bambusurils. The different importance of anion solvation and solvent expulsion from the cavity of the macrocycle in various solvents is illustrated by the fact that halide binding in water and chloroform is exclusively driven by favorable enthalpy with an entropic penalty, while in alcohols and nonpolar solvents, both favorable enthalpy and entropy contribute to anion encapsulation. DFT calculations and correlation of thermodynamic data with the solvent Swain acity parameter further underscore the importance of solvent effects on anion binding by bambusurils.
ER -
FIALA, Tomáš, Kristína SLEZIAKOVÁ, Kamil MARŠÁLEK, Karolina SALVADORI and Vladimír ŠINDELÁŘ. Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents. \textit{Journal of Organic Chemistry}. WASHINGTON: AMER CHEMICAL SOC, 2018, vol.~83, No~4, p.~1903-1912. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.7b02846.
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