104-73-4Relevant articles and documents
The Interaction of Alkylammonium Salts with Synthetic Clays. A Fluorescence and Laser Excitation Study
Nakamura, T.,Thomas, J. K.
, p. 641 - 644 (1986)
The interaction of surfactants with synthetic clays has been studied by a steady-state and a time-resolved fluorescence quenching method.The fluorescence quenching of 4-(1-pyrenyl)butyltrimethylammonium ion (PN(1+)) adsorbed on colloidal laponite clay by coadsorbed alkylpyridinium ions showed unusual behavior.Increasing the quencher concentration at first led to an efficient quenching of PN(1+) flourescence, but on increasing the quencher concentration further a reverse effect is observed, whereby the fluorescence started to recover, only to be followed by a smaller degree of quenching.The degree of recovery was strongly dependent on the chain length of the alkylpyridinium ions, the longer the chain length the larger the degree of recovery.PN(1+) fluorescence was also quenched by laponite clay itself or cupric ion in copper-clay, where cupric ion was constructed in the clay lattice.However, coadsorbed hexadecyltrimethylammonium ions (CTAB cations) dramatically reduced the quenching.The results can be explained in terms of the change of geometrical arrengement of PN(1+) adsorbed on clay.Quenching of PN(1+) fluorescence by dimethylaniline, nitrobenzene, and nitromethane in the CTAB-laponite system obeyed Poisson type kinetics, indicating that the adsorbents exist in the form of clusters or zones on the clay surface.
Synthesis of imidazolium and pyridinium-based ionic liquids and application of 1-alkyl-3-methylimidazolium salts as pre-catalysts for the benzoin condensation using solvent-free and microwave activation
Aupoix, Audrey,Pégot, Bruce,Vo-Thanh, Giang
, p. 1352 - 1356 (2010)
An efficient one-pot procedure for the synthesis of ionic liquids based on nitrogen-containing heterocycles, imidazolium or pyridinium under 'green chemistry' conditions has been described. Imidazolium salts and DBU have been found to catalyze efficiently the benzoin condensation giving good yields within very short reaction time using solvent-free microwave activation conditions.
Preparation of the pyridinium salts differing in the length of the N-alkyl substituent
Marek, Jan,Stodulka, Petr,Cabal, Jiri,Soukup, Ondrej,Pohanka, Miroslav,Korabecny, Jan,Musilek, Kamil,Kuca, Kamil
, p. 1967 - 1972 (2010)
Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents.
Scalable synthesis of ionic liquids: Comparison of performances of microstructured and stirred batch reactors
Iken, Hicham,Guillen, Frédéric,Chaumat, Hélène,Mazières, Marie-Rose,Plaquevent, Jean-Christophe,Tzedakis, Théodore
, p. 3474 - 3477 (2012)
A range of alkylpyridinium bromide ionic liquids have been synthesized in a stirred reactor at multigram scale and characterized by physical methods (viscosity, conductivity, melting point, electrochemical window, and water content). One ionic liquid, octylpyridinium bromide, was chosen to be synthesized in both macro and reduced scale reactors, in order to compare its performance and to afford evidence of the advantages of a cross channel micro reactor (channel width = 1 mm) compared to a stirred reactor.
Binding of N-Alkylpyridinium Chlorides to Nonionic Micelles
Shirahama, Keishiro,Nishiyama, Yoshinori,Takisawa, Noboru
, p. 5928 - 5930 (1987)
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.
Critical Role of Achiral Guest Molecules in Planar Chirality Inversion of Alanine-Appended Pillar[5]arenes
Park, Jaehyeon,Choi, Yeonweon,Lee, Shim Sung,Jung, Jong Hwa
, (2019)
Planar chirality inversion of pillar[5]arenes bearing d- or l-alanine substituents on both rims was investigated upon addition of guest molecules having pyridinium or imidazole moieties and long alkyl chains. The d- and l-alanine-substituted pillar[5]arenes exhibited pS and pR planar chirality, respectively. However, this planar chirality was inverted upon inclusion of certain achiral molecules, comprising pyridinium or imidazole moieties and long alkyl chains with terminal hydroxyl or methyl groups.
Ultrafast dynamics in aromatic cation based ionic liquids: A femtosecond raman-induced kerr effect spectroscopic study
Shirota, Hideaki,Kakinuma, Shohei,Takahashi, Kotaro,Tago, Akito,Jeong, Hocheon,Fujisawa, Tomotsumi
, p. 1106 - 1128 (2016)
We studied the ultrafast dynamics of 40 aromatic cation based ionic liquids (ILs) by means of femtosecond Ramaninduced Kerr effect spectroscopy. The low-frequency Kerr spectra (ca. 0.3700 cm1) of the ILs were obtained from the Kerr transients by Fourier-Transform deconvolution analysis. The low-frequency Kerr spectra in the frequency range less than 200 cm-1 coming mainly from the intermolecular vibrations for the ILs were discussed in terms of (i) anion dependence, (ii) imidazolium cations vs. pyridinium cations, (iii) alkyl group dependence, and (iv) effect of methylation in aromatic cations. Several liquid properties, such as density, viscosity, electrical conductivity, and surface tension, of the present sample ILs at 293K were also estimated in this study. We clarified that the aromatic cation based ILs show a different relation of the first moment of the low-frequency spectral band to the bulk liquid parameter, which is the square root of surface tension divided by liquid density, from aprotic molecular liquids. The slope of the first moment to the bulk parameter for the aromatic cation based ILs is gentler than that for aprotic molecular liquids.
Micelle formation as a factor influencing the mode(s) of metal ion partitioning into: N -alkylpyridinium-based ionic liquids (ILs): Implications for the design of IL-based extraction systems
Wankowski, James L.,Kaul, Michael J.,Dietz, Mark L.
supporting information, p. 5674 - 5682 (2017/12/06)
Prior studies of metal ion partitioning between an acidic aqueous phase and an ionic liquid in the presence of a macrocyclic polyether have demonstrated that the overall partitioning is a composite of three distinct pathways: neutral complex/ion-pair extraction, exchange of a cationic metal-crown ether (CE) complex for the cationic constituent of the IL, and exchange of the metal ion for a hydronium ion in a CE-H3O+ complex formed during acid preconditioning of the IL. The obvious undesirability of the ion-exchange pathways, which can lead to substantial loss of the IL cation to the aqueous phase, has led to efforts to identify means by which these processes can be suppressed or eliminated. Prior work with N,N′-dialkylimidazolium and quaternary ammonium bis [(trifluoromethyl)sulfonyl]imides has shown that increasing the hydrophobicity of the IL cation can be an effective means of diminishing the contribution of ion-exchange. Work with the corresponding N-alkylpyridinium ILs, however, indicates that in certain instances, an increase in the hydrophobicity of the IL cation is accompanied by a marked increase in its propensity to self-associate, leading to the formation of micelles in the aqueous phase. The net effect is to diminish or even negate the expected beneficial effect of IL cation hydrophobicity in reducing the contribution of ion exchange to the overall metal ion partitioning process, adversely impacting the "greenness" of extraction processes employing these ILs.
Effect of some pyridinium based compounds on the hydrolysis of carboxylate ester
Singha, Namrata,Ghosh, Kallol K.,Marek, Jan,Kuca, Kamil
experimental part, p. 611 - 616 (2012/08/08)
Nucleophilic reactivity of some pyridinium based compounds towards hydrolysis of p-nitrophenyl acetate (PNPA) has studied at pH 9.0 and temperature 27°C. The nucleophilic reactivity of newly synthesized pyridinium compounds has compared with commercially available pyridinium based compounds such as pralidoxime and dodecylpyridinium bromide. It has been observed that with an increase in the concentration of these compounds there is an increase in the first rate constant of the reaction. The apparent acid dissociation constant (pKj of some compounds have also been determined spectrophotometrically. Oximate ions released from 3-hydroxyiminomethyl-i-dodecylpyridinium bromide (3-HIDDPB) and pralidoxime have proved to be better nucleophilic agents for cleavage of carboxylate ester. Present investigation explores the structure-activity relationship of some pyridinium based compounds with same alkyl tail length.
Synthesis, characterization and conductivity of quaternary nitrogen surfactants modified by the addition of a hydroxymethyl substructure on the head group
Jordan, Deborah,Tan, Eng,Hegh, Dylan
, p. 587 - 592 (2012/10/29)
Two novel series of hydroxymethyl group-appended quaternary nitrogen surfactants (QNSs) based on the aliphatic N-alkyl-trimethylammonium and aromatic N-alkylpyridinium head groups were synthesized from the appropriate nitrogen head group precursor and 1-bromoalkane. The QNSs were characterized using 1H and 13C nuclear magnetic resonance and infrared spectroscopy, and their purity confirmed using elemental analysis. The solution behavior of the QNSs was investigated by conductivity, assessing both the aggregation concentration as well as the amount of counter-ion dissociation. The results showed a general decrease in the aggregation concentration for the compounds with the hydroxymethyl addition, where the pyridinium compounds were more affected than the ammonium QNSs. In contrast, the extent of counter-ion dissociation (α) from the aggregate was slightly increased for the ammonium compounds but that of the pyridinium compounds was not generally affected by the structural modification.
