The hydration of hydrophobic substances

Mikheev, Yu. A.; Guseva, L. N.; Davydov, E. Ya.; Ershov, Yu. A.

doi:10.1134/s0036024407120011

Cited by 24 publications

(12 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This result suggests that, under on‐water conditions, the reactants form endo complexes through their inclusion into the resorcinarene cavities driven by the hydrophobic aggregation. In accord with the hydrophobic‐hydration model, the bridging water molecules establish minimal van‐der‐Waals contacts with the reactants. Finally, attenuated total reflection infrared (ATR‐IR) studies corroborated by DFT calculations clearly evidenced the presence of H‐bonding interactions between the resorcinarene OH groups and the chlorine atom of benzyl chloride.…”

Section: Resultssupporting

confidence: 86%

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

et al. 2019

View full text Add to dashboard Cite

Metal‐free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on‐water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H‐bonding interactions with catalyst 1 a. In fact, under on‐water conditions the hydrophobic amplification of the strength of the H‐bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C−Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on‐water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on‐water procedure was extended to the gram‐scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

show abstract

Section: Resultssupporting

confidence: 86%

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

et al. 2019

View full text Add to dashboard Cite

show abstract

“…While the hydrophilic amides form strong hydrogen bonds (HB) with the water molecules, the more hydrophobic amides lead to the spontaneous formation of empty water molecule cavities capable of accommodating hydrophobic functional groups. 2 One main objective of this work is to find out how the change in hydrophilicity influences the thermodiffusive behavior.…”

Section: Introductionmentioning

confidence: 99%

Peptide model systems: Correlation between thermophilicity and hydrophilicity

Niether

Kriegs

Dhont

et al. 2018

The Journal of Chemical Physics

View full text Add to dashboard Cite

In recent years, the response of biomolecules to a temperature gradient has been utilized to monitor reactions of biomolecules, but the underlying mechanism is not well understood due to the complexity of the multicomponent system. To identify some underlying principles, we investigate the thermal diffusion of small amide molecules in water systematically. We re-analyze previous measurements of urea and formamide and compare the results with acetamide, N-methylformamide, and N,N-dimethylformamide, amides with a lower hydrophilicity. It turns out that less hydrophilic substances do not show the typical temperature dependence of water soluble macromolecules. Analyzing temperature and concentration dependent measurements using an empirical expression originally derived for nonpolar mixtures, we find that the so-called isotope contribution depends strongly on the hydrophilicity of the solute. This can be qualitatively understood by comparing with molecular dynamic simulations of Lennard-Jones fluids. The hydrophobic/hydrophilic balance also influences the structure in the fluid and with that the thermal expansion coefficient, which correlates with the thermal diffusion coefficient. Furthermore, we observe a clear correlation of the temperature and concentration dependence of the Soret coefficient with the hydrophilicity, which can be quantitatively described by the partition coefficient log P.

show abstract

“…The hydrophobic molecule and water molecules interact through multiple van der Waals forces forming hydration structure because of exibility in the spatial arrangement of water molecules. 45,46 Hydrogen bonds (H-bonds) between water molecules have been induced and formed around hydrocarbons as the hydrophobic hydration in the CO 2 solvent system. Moreover, due to non-zero dipole attractions of water molecules, the cluster of hydration is observed around ions (Na + and Cl À ) in SC-CO 2 conditions too.…”

Section: Hydrophobic Hydration Of Hydrocarbonsmentioning

confidence: 99%

Diffusivity and hydrophobic hydration of hydrocarbons in supercritical CO₂ and aqueous brine

et al. 2020

View full text Add to dashboard Cite

show abstract

The hydration of hydrophobic substances

Cited by 24 publications

References 22 publications

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

Peptide model systems: Correlation between thermophilicity and hydrophilicity

Diffusivity and hydrophobic hydration of hydrocarbons in supercritical CO₂ and aqueous brine

Contact Info

Product

Resources

About

The hydration of hydrophobic substances

Cited by 24 publications

References 22 publications

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions

Peptide model systems: Correlation between thermophilicity and hydrophilicity

Diffusivity and hydrophobic hydration of hydrocarbons in supercritical CO2 and aqueous brine

Contact Info

Product

Resources

About

Diffusivity and hydrophobic hydration of hydrocarbons in supercritical CO₂ and aqueous brine