The physical significance of the Kamlet–Taft<i>π</i>* parameter of ionic liquids

Weiß, Nadine; Schmidt, Caroline H.; Thielemann, Gabi; Heid, Esther; Schröder, Christian; Spange, Stefan

doi:10.1039/d0cp04989a

Cited by 31 publications

(22 citation statements)

References 99 publications

(156 reference statements)

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“…The relationship between the rate constant in a solvent 𝑘 𝐶 𝑆𝑜𝑙𝑣𝑒𝑛𝑡 and the solvent properties is expressed in Eq. 8 (Kamlet et al, 1981;Nikolć et al, 2010;Weiß et al, 2021).…”

Section: Kamlet-abboud-taft (Kat) Equationmentioning

confidence: 99%

Solvent effect investigation on the acid-catalyzed esterification of levulinic acid by ethanol aided by a Linear Solvation Energy Relationship

Baco

Klinksiek

Zakaria

et al. 2022

Chemical Engineering Science

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Section: Kamlet-abboud-taft (Kat) Equationmentioning

confidence: 99%

Solvent effect investigation on the acid-catalyzed esterification of levulinic acid by ethanol aided by a Linear Solvation Energy Relationship

Baco

Klinksiek

Zakaria

et al. 2022

Chemical Engineering Science

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“…An opposite behavior is expected for the α ‐value of the Kamlet–Taft‐parameters describing the hydrogen bond donating capability. Although similar π *‐values of the Kamlet–Taft‐parameters were observed for TFl and TFAc indicating similarity in bipolarity/polarizability, the π *‐value slightly increases in the order 29 :

FAP < {NTf}_{2} < TFl goodbreak= TFAc .

…”

Section: Resultsmentioning

confidence: 53%

“…However, polarity discussion of ionic liquids is more complex compared to viscosity discussion because various methods have been used for polarity investigation of ionic liquids on the one hand and the results strongly depend on the interactions between the single probes used and the ionic liquids on the other hand 28,29 . As shown in the reference, 28 the β ‐value of the Kamlet–Taft‐parameters increases in the order:

FAP < {NTf}_{2} < TFl < TFAc .

…”

Section: Resultsmentioning

confidence: 99%

Synthesis and photoinitiated polymerization of new ionic liquid methacrylates

Strehmel

Kaestner

Strehmel

2022

Journal of Polymer Science

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Synthesis of new ionic liquid methacrylates and dimethacrylates is described comprising ammonium structures and various anions (bis(trifluoromethylsulfonyl)imide (NTf2), tris(pentafluoroethyl)trifluorophosphate (FAP), triflate (TFl), and trifluoroacetate (TFAc)). The structure of the anion has a stronger effect on both melting behavior and photopolymerization kinetics compared to the cation pattern. Photo‐differential scanning calorimetry investigation shows significant differences in the polymerization rate and final conversion depending on both the polymerization technique (bulk or solution polymerization using an ionic liquid as solvent) and the ionic liquid monomer under consideration. The results show that NTf2 or FAP should be preferred as anion over TFl and TFAc in the crosslinking photoinitiated polymerization because NTf2 and FAP result in both faster polymerization and higher final conversion. Interestingly, the presence of an ionic liquid methacrylate comprising the same anion as the ionic liquid dimethacrylate during the photoinitiated polymerization of the ionic liquid dimethacrylates results in an increase in final conversion that may be caused by lower crosslink density of the network formed, and therefore, higher mobility during the crosslinking process.

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“…As polarizability increases, Coulomb interactions are reduced and ion mobility rises [ 42 ]. The α p of [C 1 OC 2 mim][Ala] is lower than [C 2 OC 2 mim][Ala], so its Coulomb interactions are stronger.…”

Section: Resultsmentioning

confidence: 99%

A New Compartmentalized Scale (PN) for Measuring Polarity Applied to Novel Ether-Functionalized Amino Acid Ionic Liquids

Guo

et al. 2022

Molecules

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Functionalized and environmentally friendly ionic liquids are required in many fields, but convenient methods for measuring their polarity are lacking. Two novel ether-functionalized amino acid ionic liquids, 1-(2-methoxyethyl)-3-methylimidazolium alanine ([C1OC2mim][Ala]) and 1-(2-ethoxyethyl)-3-methylimidazolium alanine ([C2OC2mim][Ala]), were synthesized by a neutralization method and their structures confirmed by NMR spectroscopy. Density, surface tension, and refractive index were determined using the standard addition method. The strength of intermolecular interactions within these ionic liquids was examined in terms of standard entropy, lattice energy, and association enthalpy. A new polarity scale, PN, is now proposed, which divides polarity into two compartments: the surface and the body of the liquid. Surface tension is predicted via an improved Lorentz-Lorenz equation, and molar surface entropy is used to determine the polarity of the surface. This new PN scale is based on easily measured physicochemical parameters, is validated against alternative polarity scales, and is applicable to both ionic and molecular liquids.

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The physical significance of the Kamlet–Taftπ* parameter of ionic liquids

Abstract: The Kamlet–Taft dipolarity/polarizability parameters π* for various ionic liquids were determined using 4-tert-butyl-2-((dicyanomethylene)-5-[4-N,N-diethylamino)-benzylidene]-Δ3-thiazoline and 5-(N,N-dimethylamino)-5′-nitro-2,2′-bithiophene as solvatochromic probes.

Cited by 31 publications

References 99 publications

Solvent effect investigation on the acid-catalyzed esterification of levulinic acid by ethanol aided by a Linear Solvation Energy Relationship

Solvent effect investigation on the acid-catalyzed esterification of levulinic acid by ethanol aided by a Linear Solvation Energy Relationship

Synthesis and photoinitiated polymerization of new ionic liquid methacrylates

A New Compartmentalized Scale (PN) for Measuring Polarity Applied to Novel Ether-Functionalized Amino Acid Ionic Liquids

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