104-74-5Relevant articles and documents
Structure-activity relationship modeling and experimental validation of the imidazolium and pyridinium based ionic liquids as potential antibacterials of mdr acinetobacter baumannii and staphylococcus aureus
Semenyuta, Ivan V.,Trush, Maria M.,Kovalishyn, Vasyl V.,Rogalsky, Sergiy P.,Hodyna, Diana M.,Karpov, Pavel,Xia, Zhonghua,Tetko, Igor V.,Metelytsia, Larisa O.
, p. 1 - 15 (2021)
Online Chemical Modeling Environment (OCHEM) was used for QSAR analysis of a set of ionic liquids (ILs) tested against multi-drug resistant (MDR) clinical isolate Acinetobacter baumannii and Staphylococcus aureus strains. The predictive accuracy of regression models has coefficient of determination q2 = 0.66 ? 0.79 with cross-validation and independent test sets. The models were used to screen a virtual chemical library of ILs, which was designed with targeted activity against MDR Acinetobacter baumannii and Staphylococcus aureus strains. Seven most promising ILs were selected, synthesized, and tested. Three ILs showed high activity against both these MDR clinical isolates.
Liquid-crystalline ionic liquids
Bowlas, Christopher J.,Bruce, Duncan W.,Seddon, Kenneth R.
, p. 1625 - 1626 (1996)
Low-melting point salts, the basis of industrially relevant ionic liquids, exhibit smectic A mesophases over extended temperature ranges.
Synthesis, spectroscopic and molecular docking studies of imidazolium and pyridinium based ionic liquids with HSA as potential antimicrobial agents
Trush, Maria M.,Semenyuta, Ivan V.,Vdovenko, Sergey I.,Rogalsky, Sergiy P.,Lobko, Evgeniya O.,Metelytsia, Larisa O.
, p. 692 - 699 (2017)
The interaction between human serum albumin (HSA) and synthesized imidazolium and pyridinium based ionic liquids (ILs), as good potential microbial growth inhibitors, was investigated by spectroscopic techniques combined with molecular docking analysis. All compounds were significant active against the tested bacterial and fungal strains. FT-IR spectroscopy indicated that the interaction of HSA with ILs generates considerable changes in protein secondary structure. The results of the molecular docking study showed that the studied ILs are able to firmly bind in the subdomain IIA of HSA with almost equal binding affinity (about ?6.23 kcal/mol). Investigated HSA–ILs complex binds through hydrogen bonding or/and cation-π interactions. This study provides a better understanding of the binding of imidazolium and pyridinium based ILs to HSA and opens the way for their further biological and pharmaceutical investigations as candidates with antimicrobial properties.
Anion Analysis of Ionic Liquids and Ionic Liquid Purity Assessment by Ion Chromatography
Rutz, Christina,Schmolke, Laura,Gvilava, Vasily,Janiak, Christoph
, p. 130 - 135 (2017)
The simultaneous determination of halide impurities (fluoride, chloride, bromide, and iodide) and ionic liquid (IL) anions (tetrafluoroborate, hexafluorophosphate, and triflimide) using ion chromatography was developed with a basic, non-gradient ion chromatography system. The non-gradient method uses the eluent Na2CO3/NaHCO3in water/acetonitrile (70:30 v:v) on the AS 22 column to enable a rapid and simultaneous analysis of different IL and halide anions within an acceptable run-time (22 min) and with good resolution R of larger than 2.4, a capacity k′ between 0.4 and 5.1, selectivities α between 1.3 and 2.1, and peak asymmetries Asof less than 1.5. Halide impurities below 1 ppm (1 mg·L–1of prepared sample solution) could be quantified. A range of ionic liquids with tetrafluoroborate [BF4]–, hexafluorophosphate [PF6]–, and bis(trifluoromethylsulfonyl)imide (triflimide) [NTf2]–anions combined with cations based on imidazole, pyridine, and tetrahydrothiophene could be analyzed for their anion purity. The IL-cations do not influence the chromatographic results. With the analysis of 18 ILs differing in their cation-anion combination we could prove the general applicability of the described method for the anion purity analysis of ionic liquids with respect to halide ions. The IL-anion purity of most ILs was above 98 wt %. The highest IL-anion purity was 99.8 wt %, implying anion impurities of only 0.2 wt %. The used halide anion from the synthesis route was the major anion impurity, yet with chloride also bromide and fluoride (potentially from hydrolysis of [BF4]–) were often detected. When iodide was used, at least chloride but sometimes also bromide and fluoride was present. However, even if the IL-anion content is above 99 wt %, it does not necessarily indicate an ionic liquid devoid of other impurities. From the IC analysis, one can also deduce a possible cation impurity if one takes into account the expected (calculated) IL-anion content. A matching experimental and theoretical IL-anion content excludes, a higher experimental content indicates the presence of residual KBF4, NH4PF6, or LiNTf2salt from the halide to IL-anion exchange.
AN IMPROVED PROCESS FOR PREPARATION OF QUATERNARY PYRIDINIUM SALTS
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Page/Page column 11, (2019/08/08)
The present invention discloses a process for the production of quaternary pyridinium salts and hydrates thereof. In this process, Cetylpyridinium chloride monohydrate with high purity and yield is obtained by reacting Cetyl chloride, pyridine, and water and Laurylpyridinium chloride monohydrate with high purity and yield is obtained by reacting Lauryl chloride, pyridine, and water. The process disclosed herein is simple, cost-effective and eco-friendly and produces quaternary pyridinium salts and hydrates thereof having high purity and yield at industrial scale.
One-pot synthesis of cationic amphiphiles from n-alcohols and allyl alcohols
Narender, Tadigoppula,Madhur, Gaurav,Dharamsheela,Reddy, K. Papi,Sarkar,Sarkar,Tripathi
supporting information; experimental part, p. 1687 - 1692 (2011/09/14)
A novel, efficient one-pot method has been developed to synthesize amphiphiles such as N-alkylated/N-allylated triethyl-amines and pyridinium salts for the first time from n-alcohols and naturally occurring terpenes (allyl alcohols) in good yields. These amphiphiles have got industrial application as surfactants, DNA carriers, and other biological applications. The DNA delivery efficacy and cytotoxicity of N-alkylated and N-allylated triethylamine and pyridinium salts were studied. Georg Thieme Verlag Stuttgart · New York.
Binding of N-Alkylpyridinium Chlorides to Nonionic Micelles
Shirahama, Keishiro,Nishiyama, Yoshinori,Takisawa, Noboru
, p. 5928 - 5930 (2007/10/02)
Binding of N-alkylpyridinium chlorides (C10, C12, and C14) to dodecyl oxyethylene ether (C12E6 and C12E8) micelles is determined in the presence of 5 mol m-3 NaCl at various temperatures by potentiometry which employs an electrode responsive to the surfactants.Binding affinity is expressed in terms of a distribution coefficient, Kx, of a cationic surfactant between the aqueous bulk phase and the nonionic micellar phase, and is larger for an alkylpyridinium cation with a longer hydrocarbon chain.The values of Kx are divided into three regions depending on the mole fraction of bound cationic surfactant in a micelle, X.At X x remains constant, while for 0.02 0.2.The constant Kx values reflect an intrinsic binding affinity (K0).With increase in X, electrostatic repulsion among bound cationic surfactants causes decreased Kx values, which may be analyzed by a simple electrostatic theory to estimate the position of bound cationic head groups.From the temperature dependence of K0, it is found that the binding process is nearly athermal for C12E8 micelles but exothermic for C12E6 micelles, the latter associated with the growth of micellar size with temperature.
