Thermodynamics of Halide Binding to a Neutral Bambusuril in
Water and Organic Solvents

J 2018

Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents

FIALA, Tomáš; Kristína SLEZIAKOVÁ; Kamil MARŠÁLEK; Karolina SALVADORI; Vladimír ŠINDELÁŘ et al.

Základní údaje

Originální název

Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents

Autoři

FIALA, Tomáš ; Kristína SLEZIAKOVÁ; Kamil MARŠÁLEK; Karolina SALVADORI a Vladimír ŠINDELÁŘ

Vydání

Journal of Organic Chemistry, WASHINGTON, AMER CHEMICAL SOC, 2018, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.745

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/18:00100978

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

SOLVATION ENERGY RELATIONSHIPS; ANION-BINDING; LIQUID CHLOROFORM; SUPRAMOLECULAR COMPLEXES; MOLECULAR-DYNAMICS; HIGH-AFFINITY; RECOGNITION; IONS; SUBSTITUTION; RECEPTOR

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 2. 6. 2018 12:25, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

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.

Návaznosti

CZ.02.1.01/0.0/0.0/16_013/0001761, interní kód MU

Název: RECETOX RI - OP VVV (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI - OP VVV, PO 1 Posilování kapacit pro kvalitní výzkum

GA13-15576S, projekt VaV

Název: Syntéza a supramolekulární vlastnosti bambusurilů

Investor: Grantová agentura ČR, Syntéza a supramolekulární vlastnosti bambusurilů

LM2015043, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

LM2015051, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Výzkumná infrastruktura RECETOX

Citovat

FIALA, Tomáš; Kristína SLEZIAKOVÁ; Kamil MARŠÁLEK; Karolina SALVADORI a Vladimír ŠINDELÁŘ. Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents. Journal of Organic Chemistry. WASHINGTON: AMER CHEMICAL SOC, 2018, roč. 83, č. 4, s. 1903-1912. ISSN 0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.7b02846.

@article{1419371,
   author = {Fiala, Tomáš and Sleziaková, Kristína and Maršálek, Kamil and Salvadori, Karolina and Šindelář, Vladimír},
   article_location = {WASHINGTON},
   article_number = {4},
   doi = {https://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 a 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, roč.~83, č.~4, s.~1903-1912. ISSN~0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.7b02846.

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