Synthesis of the symmetrical methylene diesters from carboxylic ionic liquids

The reaction between carboxylic ionic liquids and dichloromethane, which provokes the formation of symmetrical methylene diesters, was carried out. The synthesis of these ionic liquid compounds was carried out in a microwave reactor, and the characterization by spectroscopic techniques of methylene diesters (methylene di-2-furoate, methylene di-2-picolinate, methylene dianthranilate, and methylene dioleate) is described and the crystal structures discussed. The crystal packing of methylene dianthranilate is characterized by trimer formation due to hydrogen bonding via interactions between the hydrogen atom of the primary amine group and the oxygen of the carboxylic group.

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Computational analysis of the effect of [Tea][Ms] and [Tea][H2PO4] ionic liquids on the structure and stability of Aβ(17–42) amyloid fibrils

Physical Chemistry Chemical Physics ◽

10.1039/d0cp06434c ◽

2021 ◽

Vol 23 (11) ◽

pp. 6695-6709

Author(s):

D. Gobbo ◽

A. Cavalli ◽

P. Ballone ◽

A. Benedetto

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Liquid Water ◽

Computational Analysis ◽

Amyloid Fibrils ◽

Aβ Peptides ◽

Structure And Stability ◽

Water Solutions ◽

Kinetics Of

Tight coordination of peptides by organic anions driven by hydrogen bonding affects the fibrillation kinetics of Aβ peptides in ionic liquid/water solutions.

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Understanding the role of hydrogen bonding in Brønsted acidic ionic liquid-catalyzed transesterification: a combined theoretical and experimental investigation

Physical Chemistry Chemical Physics ◽

10.1039/c6cp06502c ◽

2016 ◽

Vol 18 (48) ◽

pp. 32723-32734 ◽

Cited By ~ 6

Author(s):

Kaixin Li ◽

Yibo Yan ◽

Jun Zhao ◽

Junxi Lei ◽

Xinli Jia ◽

...

Keyword(s):

Experimental Investigation ◽

Ionic Liquid ◽

Hydrogen Bonding ◽

Catalytic Activity ◽

Ionic Liquids ◽

Acidic Ionic Liquid ◽

Brønsted Acidic Ionic Liquid ◽

Acidic Ionic Liquids ◽

Hydrogen Bonding Networks

The intra- and inter-hydrogen bonding networks that govern the catalytic activity of Brønsted acidic ionic liquids were identified.

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Two-Dimensional FTIR as a Tool to Study the Chemical Interactions within Cellulose-Ionic Liquid Solutions

International Journal of Polymer Science ◽

10.1155/2015/958653 ◽

2015 ◽

Vol 2015 ◽

pp. 1-9 ◽

Cited By ~ 12

Author(s):

Kalyani Kathirgamanathan ◽

Warren J. Grigsby ◽

Jafar Al-Hakkak ◽

Neil R. Edmonds

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Network Structure ◽

Solution Viscosity ◽

Two Dimensional ◽

Ambient Temperatures ◽

Heating And Cooling ◽

Solution Rheology ◽

Higher Temperature

In this study two-dimensional FTIR analysis was applied to understand the temperature effects on processing cellulose solutions in imidazolium-based ionic liquids. Analysis of the imidazolium ionνC2–H peak revealed hydrogen bonding within cellulose solutions to be dynamic on heating and cooling. The extent of hydrogen bonding was stronger on heating, consistent with greater ion mobility at higher temperature when the ionic liquid network structure is broken. At ambient temperatures a blue shiftedνC2–H peak was indicative of greater cation-anion interactions, consistent with the ionic liquid network structure. Both cellulose and water further impact the extent of hydrogen bonding in these solutions. The FTIR spectral changes appeared gradual with temperature and contrast shear induced rheology changes which were observed on heating above 70°C and cooling below 40°C. The influence of cellulose on solution viscosity was not distinguished on initial heating as the ionic liquid network structure dominates rheology behaviour. On cooling, the quantity of cellulose has a greater influence on solution rheology. Outcomes suggest processing cellulose in ionic liquids above 40°C and to reduce the impacts of cation-anion effects and enhance solubilisation, processing should be done at 70°C.

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Ionic Liquids and Water: Hydrophobicity vs. Hydrophilicity

Molecules ◽

10.3390/molecules26237159 ◽

2021 ◽

Vol 26 (23) ◽

pp. 7159

Author(s):

Rita F. Rodrigues ◽

Adilson A. Freitas ◽

José N. Canongia Lopes ◽

Karina Shimizu

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Aqueous Media ◽

Liquid Solution ◽

Chemical Processes ◽

Processes And Reactions ◽

High Hydrogen ◽

Ionic Liquid Solution ◽

Dynamics Simulations

Many chemical processes rely extensively on organic solvents posing safety and environmental concerns. For a successful transfer of some of those chemical processes and reactions to aqueous media, agents acting as solubilizers, or phase-modifiers, are of central importance. In the present work, the structure of aqueous solutions of several ionic liquid systems capable of forming multiple solubilizing environments were modeled by molecular dynamics simulations. The effect of small aliphatic chains on solutions of hydrophobic 1-alkyl-3-methylimidazolium bis(trifluoromethyl)sulfonylimide ionic liquids (with alkyl = propyl [C3C1im][NTf2], butyl [C4C1im][NTf2] and isobutyl [iC4C1im][NTf2]) are covered first. Next, we focus on the interactions of sulphonate- and carboxylate-based anions with different hydrogenated and perfluorinated alkyl side chains in solutions of [C2C1im][CnF2n+1SO3], [C2C1im][CnH2n+1SO3], [C2C1im][CF3CO2] and [C2C1im][CH3CO2] (n = 1, 4, 8). The last system considered is an ionic liquid completely miscible with water that combines the cation N-methyl-N,N,N-tris(2-hydroxyethyl)ammonium [N1 2OH 2OH 2OH]+, with high hydrogen-bonding capability, and the hydrophobic anion [NTf2]–. The interplay between short- and long-range interactions, clustering of alkyl and perfluoroalkyl tails, and hydrogen bonding enables a wealth of possibilities in tailoring an ionic liquid solution according to the needs.

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Dissolution of Amyloid Aggregates in Aqueous Ionic Liquid Solutions: A Case Study of Insulin Amyloid

Australian Journal of Chemistry ◽

10.1071/ch18361 ◽

2019 ◽

Vol 72 (2) ◽

pp. 81 ◽

Cited By ~ 4

Author(s):

Takahiro Takekiyo ◽

Yuka Ishikawa ◽

Erika Yamaguchi ◽

Natsuki Yamada ◽

Yukihiro Yoshimura

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Bovine Insulin ◽

Future Design ◽

Amyloid Aggregates ◽

Liquid Solutions ◽

The Difference ◽

Β Sheet

Dissolution of amyloid aggregates with high β-sheet content is required for the correct refolding of ordered protein aggregates. The dissolution of bovine insulin amyloid aggregates in five different ionic liquids (ILs) is investigated. These were comprised of three 1-butyl-3-methylimidazolium ([bmim])-based ILs, containing either SCN−, NO3−, or Cl− anions, and two alkylammonium nitrate-based ILs, ethyl- and propylammonium nitrate (EAN and PAN). A broad IL concentration range (x=0–30mol-% IL) was analysed using FTIR spectroscopy combined with the Congo red assay. On the whole, the [bmim]-based ILs showed a higher dissolution ability than EAN and PAN for all concentrations of x. It is notable that the dissolution ability of dilute aqueous IL solutions (x<15) for insulin amyloid was different to that of concentrated aqueous IL solutions (x>15). The former condition for insulin amyloid may affect dissolution based on the denaturant effect of cations and anions in the ILs. The latter condition may affect this dissolution based on the hydrogen-bonding ability (α and β values) of the ILs, as described by the Kamlet–Taft parameters. Moreover, the difference between these α and β values (α–β) was found to be a good indicator of the dissolution ability of ILs for insulin amyloid aggregates in concentrated conditions above x=20 (α–β<0, strong dissolution ability; α–β>0, weak dissolution ability). These findings may assist the future design of aqueous IL-based dissolution agents for ordered aggregated proteins.

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A Quantitative Structure Tribo-Ability Relationship Model for Predicting the Antiwear Properties of Ionic Liquids as Lubricant Additives in Dimethyl Sulfoxide

Journal of Tribology ◽

10.1115/1.4047033 ◽

2020 ◽

Vol 142 (10) ◽

Author(s):

Jiang Zhao ◽

Xinlei Gao ◽

Tao Chen ◽

Tingting Wang ◽

Yang Li

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Dimethyl Sulfoxide ◽

Structural Parameters ◽

Structural Parameter ◽

Quantitative Structure ◽

Prediction Ability ◽

Relationship Model ◽

Antiwear Properties

Abstract The structural parameters of 23 ionic liquids were calculated by the Hartree–Fock ab initio method. The relationship between the antiwear properties of ionic liquids dissolved in dimethyl sulfoxide and the structural parameters of the ionic liquids was studied using multiple linear regression analysis. A quantitative structure tribo-ability relationship model with good fitting and prediction ability was established. The results show that entropy is the most important structural parameter affecting the antiwear performance of ionic liquid-dimethyl sulfoxide systems. The entropy of the ionic liquid is related to the hydrogen bonding in the system, and an orderly arrangement of this hydrogen bonding is beneficial in terms of improving antiwear performance.

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Ionic Liquids and Poly (Ionic Liquid)s Used as Green Solvent and Ultrasound Responded Materials

Applied Environmental Materials Science for Sustainability - Advances in Environmental Engineering and Green Technologies ◽

10.4018/978-1-5225-1971-3.ch015 ◽

2017 ◽

pp. 327-346

Author(s):

Kai Li ◽

Takaomi Kobayashi

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Ir Spectroscopy ◽

Green Chemistry ◽

Two Dimensional ◽

Green Solvent ◽

Ft Ir ◽

Responsive Behavior ◽

Poly Ionic Liquid

Ionic liquids (ILs) have been known as a class of green solvent and played an important role in green chemistry in recently years. Materials based on ILs, such as poly(ionic liquid) and polymer/ILs composites, are also widely investigated and possess many unique properties and applications. In this chapter, green solvent IL is reviewed and the responsive behavior of ILs based materials to external stimulus, like ultrasound (US), is introduced. Especially, it is described that FT-IR spectroscopy was effective for analyzing hydrogen bonding in ILs, polymeric ILs and PVA/IL composites. In addition, shear viscosity and viscoelasticity measurement and techniques of two-dimensional correlation and deconvolution are applied to analyze the change of interaction between IL to different substances and US responded behavior.

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Boosting Performance by Water Solvation Shell with Hydrogen Bonds on Protonic Ionic Liquid: Insights into the Acid Catalysis of Glycosidic Bond

Catalysis Science & Technology ◽

10.1039/d0cy02459g ◽

2021 ◽

Author(s):

Kaixin Li ◽

Limin Deng ◽

Shun Yi ◽

Yabo Wu ◽

Guangjie Xia ◽

...

Keyword(s):

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Hydrogen Bonds ◽

Acid Catalysis ◽

Biological Systems ◽

Solvation Shell ◽

Water Molecules ◽

Binding Behavior ◽

Chemical And Biological Systems

Hydrogen-bonding (HB) induced by water solvation shell is vital in the chemical and biological systems. Herein, HBs related to the binding behavior of protonic ionic liquids (PIL) with water molecules...

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Tough and stretchable inorganic/organic double network ion gel containing gemini-type ionic liquid as a multiple hydrogen bond cross-linker

RSC Advances ◽

10.1039/c9ra01790a ◽

2019 ◽

Vol 9 (21) ◽

pp. 11870-11876 ◽

Cited By ~ 2

Author(s):

Tomoki Yasui ◽

Eiji Kamio ◽

Hideto Matsuyama

Keyword(s):

Hydrogen Bond ◽

Ionic Liquid ◽

Hydrogen Bonding ◽

Ionic Liquids ◽

Double Network ◽

Multiple Hydrogen Bond ◽

Ion Gel ◽

Cross Linker ◽

Ion Gels

The extensibility and toughness of inorganic/organic double-network ion gels were dramatically increased using gemini-type ionic liquids as a hydrogen bonding-based weak cross-linker.

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