Update 1 of: Ionic Liquids in Heterocyclic Synthesis

Martins, Marcos A. P.; Frizzo, Clarissa P.; Tier, Aniele Z.; Moreira, Davidson Martins; Zanatta, Nilo; Bonacorso, Hélio G.

doi:10.1021/cr500106x

Cited by 107 publications

(51 citation statements)

References 792 publications

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“…NMR spectra were recorded at 25 C in CDCl 3 , at the spectrometer frequency given in the description of each compound. Chemical shifts ( ) are given in ppm relative to tetramethylsilane for 1 H and 13 C NMR spectra and CFCl 3 for 19 F NMR spectra. Mass spectra were obtained using electron impact (EI) or electrospray (ESI) ionization, with a TOF mass analyzer used for HRMS measurements.…”

Section: Experimental General Informationmentioning

confidence: 99%

A three-component synthesis of aryl(heteroaryl)acylamides

Loska

Bukowska

2015

Org. Biomol. Chem.

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A three-component reaction of azole or azine N-oxides, 1,1-difluorostyrenes and amines gives amides of α-aryl-α-heteroarylacetic or propionic acids. The key step is 1,3-dipolar cycloaddition between N-oxide and difluorostyrene leading to the acyl fluoride intermediate, which has been identified and characterized by NMR spectroscopy. The whole process is an example of selective functionalization of C-H bonds in both 5- and 6-membered heterocyclic systems.

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Section: Experimental General Informationmentioning

confidence: 99%

A three-component synthesis of aryl(heteroaryl)acylamides

Loska

Bukowska

2015

Org. Biomol. Chem.

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“…The main applications of these compounds are in chemical synthesis, catalysis, electrochemistry, separations, and the synthesis of new materials [2][3][4][5][6][7]. The literature has shown that ILs have a range of applications, which are closely related to their properties for aggregation in solution [8,9].…”

Section: Introductionmentioning

confidence: 99%

“…Likewise during separations (extraction of products, for example) if aggregates are formed, both hydrophobic and hydrophilic compounds can be solubilized, thereby decreasing the effectiveness of the process [6]. Our own group has used ILs in organic synthesis [13][14][15], and we are interested to develop ILs that match satisfactory performance in organic synthesis. Thus, beyond the aforementioned properties of ILs, high miscibility with reactants, high diffusion, no aggregates formation, and low toxicity are desirable.…”

Section: Introductionmentioning

confidence: 99%

Anion effect on the aggregation behavior of the long-chain spacers dicationic imidazolium-based ionic liquids

Frizzo

Bender

Gindri³

et al. 2015

Colloid Polym Sci

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This work reports the study of the anion effect on the aggregation behavior of the long-chain spacers of dicationic imidazolium-based ionic liquids (ILs) in a 4.75 % (v/ v) ethanol-water solution as well as in ethanol (95 %). The anions studied were Br − , NO 3 − , BF 4 − , SCN − and NTf 2 − .Aggregation behavior was investigated by differential scanning calorimetry (DSC), conductivity, surface tension, and fluorescence. In the ethanol-water solution, the critical aggregation concentration (CAC), free energy aggregation (ΔG°a), and the ionization degree (α) all significantly decreased with the increase in anion hydrophobicity. In ethanol, the CAC and ΔG°a values also decreased with the increase in anion size and hydrophobicity. The free energy adsorption (ΔG°a ds ) data showed that the dicationic ILs have good surfactant activity, and this property improved with the decrease in the hydration radius of the anions. The anion volumes calculated also showed a good correlation with the CAC values for aggregation in ethanol-water solution and ethanol.

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“…[2][3][4] Their adjustable properties -through structural modification in cationic and anionic moieties -allow for the designing of materials with specific requirements, including functionalization with bioactive molecules. 5,6 This adjustable nature of ILs has resulted in constant development of new compounds with various applications, both in the academic and industrial sectors, where they are employed in synthetic procedures, catalysis, batteries, and selective membranes. 5,7,8 Due to the amphiphilic characteristics of ILs, aggregation is observed when the critical aggregation concentration (CAC) is achieved in solution.…”

Section: Introductionmentioning

confidence: 99%

“…5,6 This adjustable nature of ILs has resulted in constant development of new compounds with various applications, both in the academic and industrial sectors, where they are employed in synthetic procedures, catalysis, batteries, and selective membranes. 5,7,8 Due to the amphiphilic characteristics of ILs, aggregation is observed when the critical aggregation concentration (CAC) is achieved in solution. 1 This phenomenon is dependent on the IL structure, in which the cationic alkyl chain and anion structure have been shown to play important roles.…”

Section: Introductionmentioning

confidence: 99%

Elucidating Anion Effect on Nanostructural Organization of Dicationic Imidazolium-Based Ionic Liquids

Frizzo¹,

Bender²,

Gindri

et al. 2016

J. Phys. Chem. C

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This work reports the influence of anion structure (Br -, NO 3 -, BF 4 -, and SCN -) in the aggregation process of ionic liquids (ILs), derived from 1,8-bis(3-methylimidazolium-1-yl)octane, in 4.75% ethanol-water solution (v/v). The aggregation behavior was investigated using small angle x-ray scattering (SAXS), nuclear magnetic resonance (NMR), dynamic light scattering (DLS), and transmission electron microscopy (TEM). Spin-lattice relaxation times (T1), obtained by NMR, indicated that the molecular mobility of the ILs changed when aggregates are formed. 1 H-NMR showed distinct chemical shifts as a function of the concentration of [BisOct(MIM) 2 ][2X] (in which X = Br, NO 3 , SCN, and BF 4 ) in solution. This change was associated with different chemical environments experienced by the hydrogen atoms when the aggregation process occurs.This behavior was characterized by the different types of interactions in the aggregates, in accordance with the anion of the IL structure. The SAXS measurements demonstrated that the distance between two molecules, which function as scattering centers, was dependent on the anion hydrophobicity. Less hydrophobic anions resulted in shorter distances between scattering centers due to their better solvating ability. Due to the lower solvating ability of hydrophobic anions, a larger distance between two scattering centers was observed. Furthermore, ILs with more hydrophobic anions (e.g., BF 4 -) resulted in closely-packed aggregates.

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Update 1 of: Ionic Liquids in Heterocyclic Synthesis

Cited by 107 publications

References 792 publications

A three-component synthesis of aryl(heteroaryl)acylamides

A three-component synthesis of aryl(heteroaryl)acylamides

Anion effect on the aggregation behavior of the long-chain spacers dicationic imidazolium-based ionic liquids

Elucidating Anion Effect on Nanostructural Organization of Dicationic Imidazolium-Based Ionic Liquids

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