1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition
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ABSTRACT:
SUBMITTER: Madivalappa Davanagere P
PROVIDER: S-EPMC8515400 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.
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Project description:Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.
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Project description:In the title hydrated molecular salt, C(9)H(9)N(2) (+)·Cl(-)·H(2)O, the dihedral angle between the five- and six-membered rings in the cation is 18.00 (2)°. O-H⋯Cl, N-H⋯O and N-H⋯Cl hrdrogen-bonding inter-actions are present in the crystal structure.
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Project description:Crystals of four new copper(II) complexes have been grown from copper(II) acetate/chloride-1-ethyl-3-methyl-imidazolium acetate/chloride-water systems and characterized by X-ray analysis. The first complex, bis-(1-ethyl-3-methyl-imidazolium) tetra-?-acetato-bis[chloridocuprate(II)], [Emim]2[Cu2(C2H3O2)4Cl2] (1) (Emim is 1-ethyl-3-methyl-imidazolium, C6H11N2), contains [Cu2(C2H3O2)4Cl2]2- coordination anions with a paddle-wheel structure and ionic liquid cations. Two of the synthesized complexes are one-dimensional polymers, namely catena-poly[1-ethyl-3-methyl-imidazolium [[tetra-?-acetato-dicuprate(II)]-?-chlorido] monohydrate], {[Emim][Cu2(C2H3O2)4Cl]·H2O} n (2), and catena-poly[1-ethyl-3-methyl-imidazolium [[tetra-?-acetato-dicuprate(II)]-?-acetato]], {[Emim][Cu2(C2H3O2)5]} n (3). In these compounds, the Cu2(C2H3O2)4 units with a paddle-wheel structure are connected to each other through chloride (in 2) or acetate (in 3) anions to form parallel chains, between which cations of ionic liquid are situated. The last compound, bis-(1-ethyl-3-methyl-imidazolium) tetra-?-acetato-bis[aquacopper(II)] tetra-?-acetato-bis[acetatocuprate(II)] dihydrate, [Emim]2[Cu2(C2H3O2)4(H2O)2][Cu2(C2H3O2)6]·2H2O (4), contains two different binuclear coordination units (neutral and anionic), connected through hydrogen bonds between water mol-ecules and acetate ions.
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Project description:Ionic liquids (ILs) have become nearly ubiquitous solvents and their interactions with biomolecules has been a focus of study. Here, we used the fluorescence emission of DAPI, a groove binding fluorophore, coupled with molecular dynamics (MD) simulations to report on interactions between imidazolium chloride ([Imn,1]+) ionic liquids and a synthetic DNA oligonucleotide composed entirely of T/A bases (7(TA)) to elucidate the effects ILs on a model DNA duplex. Spectral shifts on the order of 500-1000 cm-1, spectral broadening (~1000 cm-1), and excitation and emission intensity ratio changes combine to give evidence of an increased DAPI environment heterogeneity on added IL. Fluorescence lifetimes for DAPI/IL solutions yielded two time constants 0.15 ns (~80% to 60% contribution) and 2.36-2.71 ns for IL up to 250 mM. With DNA, three time constants were required that varied with added IL (0.33-0.15 ns (1-58% contribution), ~1.7-1.0 ns (~5% contribution), and 3.8-3.6 ns (94-39% contribution)). MD radial distribution functions revealed that π-π stacking interactions between the imidazolium ring were dominant at lower IL concentration and that electrostatic and hydrophobic interactions become more prominent as IL concentration increased. Alkyl chain alignment with DNA and IL-IL interactions also varied with IL. Collectively, our data showed that, at low IL concentration, IL was primarily bound to the DNA minor groove and with increased IL concentration the phosphate regions and major groove binding sites were also important contributors to the complete set of IL-DNA duplex interactions.
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Project description:In this research, a novel approach to produce a novel nanocatalyst, AgBr supported on an ionic gelation (IG)-based nanomaterial, was developed through the aqueous coprecipitation approach for the dendritic fibrous nanosilica (DFNS) production and the wet impregnation method for IG coating, taking into account TPP as the cross-linking agent. In addition, DFNS/IG@Ag(i) had heterogeneous features that contributed to the quick improvement of the catalyst by filtration separation. The catalytic activity of DFNS/IG@Ag(i) was examined to synthesize β-oxopropylcarbamates through a multicomponent coupling of CO2, amines and propargyl alcohols in moderate conditions. The DFNS/IG@Ag(i) NPs were completely investigated by taking advantage of TG, TEM, FESEM and FT-IR spectroscopy analyses. The DFNS/IG@Ag(i) nanocatalyst indicated high stability in the reaction for five cycles without considerable loss of some properties like activity, which could be because of the high loading of IG on the catalyst surface.
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Project description:The title salt, C4H6N3O2 +·Cl-, exhibits multiple hydrogen-bonding inter-actions involving the nitro-imidazolium cation and the chloride anion. Strong hydrogen bonds between the amine hydrogen atom and the chloride anion link the ionic moieties. Of note, with respect to H⋯Cl inter-actions, the central aromatic hydrogen atom displays a shorter inter-action than the other aromatic hydrogen atom. Finally, inter-actions are observed between the nitro moiety and methyl H atoms. While no π-π stacking is observed, anion-π inter-actions are present. The crystal was refined as a two-component twin.
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Project description:In order to improve the total sulfur removal rate in coal combustion, an acidic ionic liquid (IL) 1-carboxymethyl-3-methylimidazolium hydrogen sulfate ([HOOCCH2mim][HSO4]) as the extractant combined with the oxidant 30% hydrogen peroxide (H2O2) was applied to reduce the total sulfur content, and its microscopic mechanism of desulfurization was analyzed. The experimental results show that the desulfurization rate of the [HOOCCH2mim][HSO4]-H2O2 (1:10) solution was 45.12% and the organic sulfur removal rate was 16.26%, which were significantly higher than those of only H2O2 or pure [HOOCCH2mim][HSO4]. Fourier-transform infrared (FTIR) spectroscopy and X-ray photoelectron spectroscopy analyses showed that the mercaptan -SH and disulfide -S-S- in coal decreased after being treated with IL-H2O2. In particular, the results of FTIR spectroscopy indicated that the relative proportion of -S-S-and -SH treated with IL-H2O2 (1:10) decreased by 31.9 and 27.2%, respectively, compared with that of a pure IL. This is due to H2O2 oxidation; -SH and -S-S- were oxidized to sulfoxide and then the sulfoxide transferred from the coal phase to the IL phase, which improved organic sulfur removal from coal. Therefore, the combination of an ionic liquid and H2O2 could increase the total desulfurization rate. In addition, the thermogravimetric analysis of coal is divided into four different stages; the weight loss during the combustion stage and the residues show that the IL-H2O2 could improve the coal combustion because of good previous swelling and destruction of bridge bonds and hydrogen bonding of coal. Besides, the fewer residues in IL-H2O2-treated coals also indicate that a less amount of inorganic substance is left in coal after IL-H2O2 desulfurization, which is consistent with the desulfurization results.
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Project description:The asymmetric unit of the title compound, C(11)H(13)N(2) (+)·Cl(-), contains two independent ion pairs and and half a solvent water mol-ecule (m site symmetry for the O atom). The imidazole ring is oriented at dihedral angles of 66.61?(3) and 89.17?(3)° with respect to the aromatic ring in the two cations. In the crystal, O-H?(O,Cl) hydrogen bonds and ?-? stacking inter-actions between the imidazole ring of one mol-ecule and the aromatic ring of another [perpendicular distance = 3.4?(4)?Å] link the mol-ecules.
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