Synthesis Of Salts Research Articles

An efficient three-component synthesis of new amidinium salts

A simple and efficient method for the synthesis of new amidinate salts containing barbiturate moiety by a three-component condensation reaction of C–H acids, pyrimidine-tetraone and 1,8-diazabicycloundec-7-ene (DBU) in refluxing CHCl3 without any catalyst is reported. The structures of these compounds were confirmed by IR, MS, 1H-NMR, 13C-NMR, and single-crystal X-ray diffraction studies. .

ChemInform Abstract: Synthesis of Novel Benzimidazolium Salts of Biologically Active Chalcogenylacetic Acids.

Novel potentially biologically active benzimidazolium-based salts, some of them being ionic liquids, were synthesized by the reaction between substituted benzimidazoles and biologically active acetic acid derivatives RYCH 2 CO 2 H (R = Ar, 3-indolyl; Y = O, S).

The First Example of 3,7-Diazabicyclo[3.3.1]nonane Synthesis by Aminomethylation of Guareschi Imide Salts

2,6-Dioxopiperidine-3,5-dicarbonitriles (also known as Guareschi imides) and their salts are readily prepared by condensation of ketones, cyanoacetic ester, and ammonia [1-3] and have proved over more than a century to be convenient reagents for synthesizing derivatives of glutarimide, 3,3-disubstituted glutaric acids [46], azaspiranes [7], etc. A single method has been reported in the literature for the cyclization of Guareschi imides to bispidines (3,7-diazabicyclo[3.3.1]nonane derivatives) under conditions of acid hydrolysis of the nitrile groups [4, 8-11]. The compounds obtained are of interest as intermediate products in the preparation of substances with anti-ischemic activity [12] and of sparteine alkaloids [13]. We have previously reported a convenient method for the synthesis of 4-monosubstituted Guareschi imide salts by the reaction of 3-aryl-2-cyanoacrylamides with cyanoacetylpyrazole [14, 15]. These compounds, and other known 2,6-dioxopiperidine-3,5-dicarbonitriles are of general interest (as C-3/C-5 dinucleophilic reagents) for the preparation of substituted bispidines via a double aminomethylation reaction. The Mannich reaction of 3,5-dinucleophilic pyridine derivatives is one of the most generally applicable methods of preparing 3,7-diazabicyclo[3.3.1]nonanes [16, 17]. However, to this time there was no published evidence for the aminomethylation of Guareschi imides. We have found that the reaction of the glutarimide salt 1a with benzylamine and an excess of formaldehyde occurred under mild conditions to give the 2,4-dioxo-3,7-diazabicyclo[3.3.1]nonane salt ("bispidinate") 2. Reaction of salt 1a with -phenethylamine and salt 1b with benzylamine proceeded similarly. Acidification gave the expected bispidines 3a,b. These reactions serve as a first example of the synthesis of 3,7-diazabicyclo[3.3.1]nonane derivatives using Guareschi imides. The structure of compounds 2 and 3a,b was confirmed by IR and H NMR spectroscopy data, HPLC-MS, and elemental analysis. Optimization of the conditions, limits, and potential uses of the reaction will be the subject of future investigations.

Knowledge-based hydrogen bond prediction and the synthesis of salts and cocrystals of the anti-malarial drug pyrimethamine with various drug and GRAS molecules

We have previously reported on hydrogen bond propensity calculations for the potential formation of adducts between pyrimethamine and dicarboxylic acids. Here we extend the range of potential synthon interactions using a variety of potential coformers. Specifically calculations were performed to predict the possibility of the formation of molecular adducts, 1a–1h, between the anti-malarial drug pyrimethamine (1) and (a) carbamazepine, (b) theophylline, (c) aspirin, (d) α-ketoglutaric acid, (e) saccharin, (f) p-coumaric acid, (g) succinimide and (h) L-isoleucine. The bonds of highest propensity were predicted between 1 and coformers (b–h), indicating a high probability of formation of adducts between 1 and b–h. In contrast the bonds of highest propensity were between reactants and the solvent for the adduct 1a, indicating either a high probability of the reactants crystallizing as solvates or incorporation of solvent into the adduct lattice. Experimental results agreed with the propensity calculations with the formation of a solvated cocrystal (1a·CH3OH). The successful application of hydrogen bond propensity calculations to the prediction of likely outcomes of these cocrystallization reactions suggests that this may be a useful tool in designing more targeted screening experiments.

Synthesis and Antimicrobial Activities of Phosphonium Salts on Basis of Triphenylphosphine and 3,5-Di-Tert-Butyl-4-Hydroxybenzyl Bromide

We report the structures of two new phosphonium salts prepared via the reaction of (substituted)benzyl bromides with triphenylphosphine. The antibacterial and antifungal activities are reported.

Novel atom-economic reaction: comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts

A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH–H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.

Sonochemical Synthesis of Polypyrrole Salt and Study of its Cr(VI) Sorption-Desorption Properties

Polypyrrole salt of desired structure has been synthesized sonochemically and characterized by chemical, spectral and thermal analysis. Surface morphology of the polymer is examined by scanning electron microscope (SEM). Chromium(VI) sorption-desorption properties of the polymer has been studied through optimization of pH, contact time and temperature. Selectivity towards Cr(VI) sorption in the presence of competitive ions has been tested. The relevant kinetic parameters are evaluated to elucidate the sorption-desorption mechanism. The metal binding capacity of the polymer is compared with the commercially available ion-exchangers.

Electrochemical Synthesis of Tetra Alkyl Ammonium Salt Stabilized Gold Nanoparticles

Gold nanoparticles are of great interest for nanoelectronics and other applications. For this, it is important that all particles have controllable size and shape. The authors thus report the size-selective synthesis of tetra alkyl ammonium salt stabilized gold nanoparticles using electrochemical reduction method. Gold nanoparticles in the range of 8.1–10.9 nm are synthesized by using gold as sacrificial anode and platinum as inert cathode. By using a series of tetra alkyl ammonium salts (TEAB, TPAB, TBAB, and TOAB) and varying the current density (6 and 10 mA/cm2) size selection can be achieved. The colloids and nanoparticles are characterized by UV-visible spectroscopy, XRD, XPS, and TEM.

Spectroscopic and atomic force microscopy characterization of the electrografting of 3,5-bis(4-diazophenoxy)benzoic acid on gold surfaces

The synthesis of a bipodal diazonium salt, 3,5-bis(4-diazophenoxy)benzoic acid, and the study of its electrochemical deposition on gold surfaces is presented. The presence of the organic layer on the gold surface was characterized using atomic force microscopy and X-ray photoelectron spectroscopy, demonstrating the presence of phenyl groups, indicative of the grafted layer as well as the formation of multilayers, dependent on the electrografting conditions.

Oxidative nitration of the amino group: synthesis of dinitramide and cyanonitramide salts

A convenient preparative method for the synthesis of potassium dinitramide and cyanonitramide salts was developed. The method involves reactions of nitramide or cyanamide with KNO2 and PhI(OAc)2 or PhIO in methanol.

Synthesis of a Bi-Quaternary Ammonium Salt from Rosin and its Inhibition to some Wood Decay Fungi

An anti-fungal derivative of rosin, bi-quaternary ammonium salt (B-QAS) was synthesized. First, rosin was modified by acrylic acid. Then using this modified rosin reacted with an intermediate quaternary ammonium (epoxy propyl triethyl ammonium chloride) which was the reaction product of triethylamine and epichlorohydrin. The final product was bisN-(3-rosin acyloxy -2-hydroxy) propyl-N, N triethyl ammonium chloride. The chemical structure of the product and its functional groups was characterized by Fourier transform infrared spectroscopy (FTIR). Its yield of greater than 80% was conformed by high performance liquid chromatography (HPLC) and gravimetric analysis. Its anti-fungal activity was determined in vitro with a paper-disc method. B-QAS presented significant inhibitory effect for Trametes versicolor, Gloeophyllum trabeum and Postia placenta when its concentration was 0.5 mg/mL, whereas for Irpex lacteus the inhibitory effect was a little poor.

Electrochemical monitoring of the metabolic activity of mycobacteria in culture

Mycobacterial metabolic activity is typically measured using time-consuming manual methods based on nutrient consumption, nucleic acid synthesis or reduction of tetrazolium salts. In this study, we propose much simpler electrochemical methods for continuous monitoring of the metabolic activity of mycobacteria in culture. Chronoamperometry and chronopotentiometry were used to detect metabolic activity of both slow-growing and fast-growing mycobacteria using a potentiostat with 2D-electrochemical cell. Electrochemical measurements were able to detect statistically significant differences in the metabolic activity of approximately 10(7) mycobacteria in different growth conditions, within less than 24h of mycobacterial culture. The metabolic activity of mycobacteria measured by the used electrochemical methods correlated well with changes in general respiratory conditions within the cells as it was evaluated by different biochemical tests. Chronoamperometry and chronopotentiometry allowed measurement of mycobacterial metabolic activity without invasive chemical reactions, at minimal bacterial load and when metabolic response of mycobacteria occurs quickly. The proposed methodology is simple, rapid and cost-effective, and it is expected that both in vitro and in vivo metabolic activity of human mycobacterial pathogens as Mycobacterium tuberculosis can be measured when the implementation of this method to analyze virulent strains is adapted.

An efficient three-component synthesis of new barbiturate salts

An efficient synthesis of new barbiturate salts consist of 2-aminopyridinium moiety by a‎n uncatalyzed three-component condensation reaction of C–H acids, pyrimidine-tetraones, and 2-aminopyridines‎ in refluxing chloroform is reported. The reaction of pyrimidine-tetraones and 2-aminopyridines with ninhydrin in the formation of new barbiturate salts consist of 2-aminopyridinium moiety is also investigated.

Synthesis of nitrogen-containing metal dithiophosphates

Problems associated with synthesis of metal complexes and salts of dithiophosphates containing phosphorus, sulfur, and nitrogen heteroatoms and a sterically hindered hydroxy group in their molecule are considered.

ChemInform Abstract: 4‐(Azulen‐1‐yl) Six‐Membered Heteroaromatics Substituted with Thiophen‐2‐yl or Furan‐2‐yl Moieties in 2 and 6 Positions.

AbstractThe compounds (IV) and (V) are intensely colored.

Synthesis and dynamic NMR study of zwitterionic salts obtained from N,N′-dimethylbarbituric acid, benzaldehydes, and N,N,N′,N′-tetramethylguanidine

A synthesis of stable charge-separated tetramethylguanidinium-barbituric acid zwitterionic salts is developed through a one-pot three-component reaction of N,N′-dimethylbarbituric acid, benzaldehydes, and N,N,N′,N′-tetramethylguanidine in CH2Cl2 at room temperature. A dynamic effect was observed in the 1H nuclear magnetic resonance (NMR) spectrum of 5-[[bis(dimethylamino)methylene)ammonio](4-methylphenyl)methyl]-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide as a result of restricted rotation (ΔG ≠ = 69 kJ/mol) around the Me2N–C bonds of the guanidinium moiety.

Progress in Synthesis and Reaction of S-Benzothiophenium Salts

The synthetic methods of S-benzothiophenium salts is reviewed and the advantages and disadvantages of various methods are discussed. The (4 + 2) Diels-Alder reaction, thermolysis, photolysis, ring-opening reaction of S-phenylbenzothiophenium salts are introduced in details. And the development of the chemistry and applications of S-phenylbenzothiophenium salts is also prospected. Keywords S-benzothiophene salt; (4+2) Diels-Alder reaction; thermolysis; photolysis; ring-opening reaction

Synthesis and Characterization of Chiral Guanidines und Guanidinium Salts Derived from 1-Phenylethylamine

Synthesis and Characterization of Chiral Guanidines und Guanidinium Salts Derived from 1-Phenylethylamine

The synthesis and catalytic properties of imidazolinium salts and their palladium(II) complexes

Three 1,3-dialkylimidazolinium chloride salts and their palladium(II) complexes have been synthesized and characterized by elemental analysis, 1H NMR, 13C NMR and IR spectroscopy. The catalytic activities of the 1,3-dialkylimidazolinium chloride salts and their complexes in the Heck and Suzuki coupling reactions were investigated.

Synthesis and X-ray crystal structure of fluorous imidazolium salts

Synthesis of two salts involving CH2O spacer between the imidazole nitrogen and hexafluoroisopropyl group in the fluorous imidazolium cations is reported. Such an insertion would result in the formation of α-ammonium ether. The two fluorous imidazolium salts involve one or two -CH2OCH(CF3)2 groups attached to the imidazole nitrogen atoms. These products were synthesized from the reaction between methyimidazole and imidazole as nucleophiles and sevochlorane, ClCH2OCH(CF3)2, as electrophile, in different molar ratios. The resulting products have been characterized by 1H, 13C, and 19F NMR and FTIR spectroscopy. Also, the single crystal X-ray diffraction analysis for the symmetrically substituted imidazolium product is presented. The preliminary animal tests indicated no anesthetic property but the two tested salts were found to behave as calmative.