Synthesis and Physical Properties of Choline Carboxylate Ionic Liquids

Muhammad, Nawshad; Hossain, Mohammad Ismail; Man, Zakaria; El‐Harbawi, Mohanad; Bustam, Mohammad Azmi; Noaman, Yousr Abdulhadi; Alitheen, Noorjahan Banu Mohamed; Ng, Mei Kee; Hefter, Glenn; Yin, Chunyang

doi:10.1021/je300086w

Cited by 121 publications

(93 citation statements)

References 34 publications

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“…This is in contrast to the results of Petkovic et al [7] (where cytotoxic effects follow as be explained according to the stated in T-SAR concept [40,42]. Also the results are not in line with those of Muhammad et al, who reported that cytotoxicity of ChC m with m = 2, 3, 4, 6 on the human breast cancer cell line MCF-7 decreases with increasing chain length [8]. This study agrees partly with the results found by Petkovic et al [7] where the cytotoxicity increases with increasing chain length (see m = 2–4 and 6–10) and partly with the one of Muhammad et al [8], where the cytotoxicity decreases with increasing chain length (see m = 4–6).…”

Section: Resultscontrasting

confidence: 74%

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Effect of choline carboxylate ionic liquids on biological membranes

Rengstl

Kraus

Vorst

et al. 2014

Colloids and Surfaces B: Biointerfaces

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Choline carboxylates, ChCm, with m = 2–10 and choline oleate are known as biocompatible substances, yet their influence on biological membranes is not well-known, and the effect on human skin has not previously been investigated. The short chain choline carboxylates ChCm with m = 2, 4, 6 act as hydrotropes, solubilizing hydrophobic compounds in aqueous solution, while the longer chain choline carboxylates ChCm with m = 8,10 and oleate are able to form micelles. In the present study, the cytotoxicity of choline carboxylates was tested using HeLa and SK-MEL-28 cells. The influence of these substances on liposomes prepared from dipalmitoylphosphatidylcholine (DPPC) was also evaluated to provide insights on membrane interactions. It was observed that the choline carboxylates with a chain length of m > 8 distinctly influence the bilayer, while the shorter ones had minimal interaction with the liposomes.

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Section: Resultscontrasting

confidence: 74%

“…Choline carboxylates were found to exert only minor toxic activity on these organisms. Also Muhammad et al found just slight cytotoxic effects on the human breast cancer cell line MCF-7 for choline carboxylates ChC m with m = 2,3,4, 6 [8]. …”

Section: Introductionmentioning

confidence: 99%

Effect of choline carboxylate ionic liquids on biological membranes

Rengstl

Kraus

Vorst

et al. 2014

Colloids and Surfaces B: Biointerfaces

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“…The COSMO-RS model has been successfully used in the past to estimate the thermodynamic properties of systems containing ionic liquids, including liquid-liquid equilibrium and activity coefficients of its mixture with water or organic solutes [52][53][54][55][56][57][58][59]. After evaluating the capacity of the COSMO-RS model to describe the experimental activity coefficients, this is used to analyze and discuss the molecular interactions that affect the mixing properties of the cholinium-ionic liquids and water, which are also supported by ab initio calculations [60][61][62][63] [15,64]. Fig.…”

Section: Introductionmentioning

confidence: 99%

Assessing the activity coefficients of water in cholinium-based ionic liquids: Experimental measurements and COSMO-RS modeling

Khan

Kurnia

Sintra

et al. 2014

Fluid Phase Equilibria

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a b s t r a c tThe vapor liquid-equilibrium of water + ionic liquids is relevant for a wide range of applications of these compounds. It is usually measured by ebulliometric techniques, but these are time consuming and expensive. In this work it is shown that the activity coefficients of water in a series of cholinium-based ionic liquids can be reliably and quickly estimated at 298.15 K using a humidity meter instrument. The cholinium based ionic liquids were chosen to test this experimental methodology since data for water activities of quaternary ammonium salts are available in the literature allowing the validation of the proposed technique.The COSMO-RS method provides a reliable description of the data and was also used to understand the molecular interactions occurring on these binary systems. The estimated excess enthalpies indicate that hydrogen bonding between water and ionic liquid anion is the dominant interaction that governs the behavior of water and cholinium-based ionic liquids systems, while the electrostatic-misfit and van der Walls forces have a minor contribution to the total excess enthalpies.The results here reported show that water activity measurements allow a quick scan for selecting ionic liquids according to their behavior in mixtures with water.

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“…The instrument was calibrated with Millipore-grade water using ILs with data previously established by our research group [12][13][14]. The viscosities and densities of the ILs were measured in the temperature range of 293.15-373.15 K with ±0.01 K accuracy and uncertainties of 0.5 % and ±5 9 10 -4 gÁcm -3 , respectively.…”

Section: Viscosity and Densitymentioning

confidence: 99%

“…The standard entropies calculated within the range of 283.7-409.6 JÁmol -1 ÁK -1 are presented in Table 6 [13,24,27]. The lattice energy of a salt is associated with the potency of interactions of its ions and predicts their relative stabilities.…”

Section: Estimation Of Volumetric Propertiesmentioning

confidence: 99%

Synthesis and Thermophysical Properties of Hydrogensulfate Based Acidic Ionic Liquids

et al. 2015

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Three ionic liquids (ILs): 1-butyl-3-methyl-imidazolium hydrogensulfate [C 4 C 1 Im] [HSO 4 ], 1-butyl-imidazolium hydrogensulfate [C 4 C 0 Im][HSO 4 ], and 1-methylimidazolium hydrogensulfate [C 1 C 0 Im][HSO 4 ], were synthesized and characterized. The effect of alky group incorporation into the imidazolium cation was evaluated in terms of changes in density, surface tension, viscosity, and thermal degradation of the ILs. The viscosity and density were measured within the temperature range of 293.15-373.15 K, and experimental values of density were used to calculate molar volume, standard molar entropy, lattice energy, and thermal expansion coefficients. Glasser's approach was used to calculate the lattice energies of the ILs. Surface tensions in the temperature range of 293.15-353.15 K were also measured and surface tension values were used to estimate the surface entropy and enthalpy of the ILs. Refractive indices were measured with an ATAGO refractometer (RX-5000a) within the temperature range of 293.15-323.15 K. Thermal gravimetric analysis was performed in the temperature range of 323.15-773.15 K.

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Synthesis and Physical Properties of Choline Carboxylate Ionic Liquids

Cited by 121 publications

References 34 publications

Effect of choline carboxylate ionic liquids on biological membranes

Effect of choline carboxylate ionic liquids on biological membranes

Assessing the activity coefficients of water in cholinium-based ionic liquids: Experimental measurements and COSMO-RS modeling

Synthesis and Thermophysical Properties of Hydrogensulfate Based Acidic Ionic Liquids

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