Pyridinium chloride

Fig. XI-13. Adsorption isotherms for SNBS (sodium p-3-nonylbenzene sulfonate) (pH 4.1) and DPC (dodecyl pyridinium chloride) (pH 8.0) on mtile at approximately the same surface potential and NaCl concentration of O.OlAf showing the four regimes of surfactant adsorption behavior, from Ref. 175. [Reprinted with permission from Luuk K. Koopal, Ellen M. Lee, and Marcel R. Bohmer, J. Colloid Interface Science, 170, 85-97 (1995). Copyright Academic Press.]...

A surfactant solution is a mixture of DTAC (dodecyltrimethylammonium chloride) and CPC (cetyl pyridinium chloride) the respective CMCs of the pure surfactants are 2 X lO M and 9 x IO M (Ref. 140). Make a plot of the CMC for mixtures of these surfactants versus the mole fraction of DTAC. 

Pyridinium bromide, N-phenacyl-NMR, 2, 121 reactions, 2, 336 Pyridinium cations metabolism, 1, 234 reactivity, 2, 167 Pyridinium chloride hydrogenation, 2, 284 Pyridinium chloride, N-acyl-as acylating agent, 2, 180 Pyridinium chloride, cetyl-as antiseptic, 2, 519... 

Pyridinium chloride, N-(4-pyridyl)-hydrochloride quaternization, 2, 175 reactions with amines, 2, 241 Pyridinium chlorochromates as oxidizing agents, 2, 170 reactions, 2, 34 Pyridinium dichromate as oxidizing agent, 2, 170 Pyridinium l-dicyanomethylide... 

DETERMINATION OF l-[2-OXO-2-(TRIFLUOROMETHYL-10-PHENOTHIAZINYL)-ETHYL]-4-HYDROXYIMINOMETHYL-PYRIDINIUM CHLORIDE BY DERIVATIVE UV-SPECTROPHOTOMETRY... 

An example of the first type is the emulsion stabiliser as exemplified by sodium oleyl sulphate, cetyl pyridinium chloride and poly(ethylene oxide) derivatives. For a number of applications it is desirable that the latex be thickened before use, in which case thickening agents such as water-soluble cellulose ethers or certain alginates or methacrylates may be employed. Antifoams such as silicone oils are occasionally required. 

In 1904, Zincke reported that treatment of Al-(2,4-dinitrophenyl)pyridinium chloride (1) with aniline provided a deep red salt that subsequently transformed into A-phenyl pyridinium chloride 5 (Scheme 8.4.2). Because the starting salt 1 was readily available from the nucleophilic aromatic substitution reaction of pyridine with 2,4-dinitrochlorobenzene, the Zincke reaction provided access to a pyridinium salt (5) that would otherwise require the unlikely substitution reaction between pyridine and... 

A special type of ammonio group is represented by 4-( 1 -pyridinium)-pyridine and other azinium analogs. Such products often result from self-quaternization of highly reactive derivatives. A -(4-Pyridyl)-and A -(3-nitro-4-pyridyl)-pyridinium chloride hydrochlorides (121) react with aniline, chloride ion, and water to give 4-substituted pyridines plus pyridine. l-(2-Quinolyl)- and l-(4-quinolyl)-pyridinium salts undergo 2- and 4-substitution, respectively, with amines, anilines, hydroxylamine, phenols, alkoxides, mercaptans, and chloride... 

Tliionyl halides and A-heteroaromatics are known to be in equilibrium with the corresponding A-(halosulhnyl)heteroarylium halides. N-(Chlorosulhnyl)pyridinium chloride (36), for example, readily reacts with a second molecule of pyridine to give the A-[l-chlorosulhnyl-l,4-dihydro-pyridine-4-yl]pyridinium chloride (37a). The intermediate 37a is probably involved in the preparation of A-(pyridine-4-yl)pyridinium chloride hydrochloride (37b). However, the authors could not detect either 37a or 37b in their experiments (91CB2013) (Scheme 10). 

From a practical point of view, literature data indicate that it is not necessary in most cases to isolate the title salts prior to their reaction. Tliis can be readily understood since their preparation is nearly quantitative and sulfur dioxide is the sole product evolved during their formation. In fact, it is highly advisable to recourse to a two-step procedure during the reactions between A -(l-chloroalkyl)pyridinium chlorides and amino acids (Section IV,C,6) (97BSB383). 

It has been proposed (89JOC4808) that the first step of a reaction between an amine and an N-(l-chloroalkyl)pyridinium chloride 33 is a simple substitution of the halogen atom yielding a mixed bisonium salt 55 (pathway a in Scheme 19). Tliis is the final product when various nitrogen het-... 

Tliere is only one report concerning the reaction of A -(l-chloroalkyl)-pyridinium chlorides with secondary diamines (92BSB233). 2-Substituted 1,3-dimethyl- and 1,3-diphenyl-imidazolidines 79 have been prepared (75-95% yields) starting from either -dimethyl- or A, A -diphenylethane-1,2-diamines, respectively (Scheme 25). Reactions are particularly fast for the preparation of the 1,3-dimethylimidazolidines. Reaction times as short as 5 min have been claimed. 

Reactions between A -(l-chloroalkyl)pyridinium chlorides 33 and amino acids in organic solvents have a low synthetic value because of the low solubility of the amine partner. A special protocol has been designed and tested in order to circumvent this drawback. Soon after the preparation of the salt, an aqueous solution of the amino acid was introduced in the reaction medium and the two-phase system obtained was heated under reflux for several hours. However, this was not too successful because sulfur dioxide, evolved during the preparation of the salt, was converted into sulfite that acted as an 5-nucleophile. As a result, A -(l-sulfonatoalkyl)pyridinium betaines such as 53 were obtained (Section IV,B,3) (97BSB383). To avoid the formation of such betaines, the salts 33 were isolated and reacted with an aqueous solution of L-cysteine (80) to afford thiazolidine-4-carboxylic acids hydrochlorides 81 (60-80% yields). 

Tlie Ca substituent effects have been experimentally studied by synthesizing and investigating the A -(l,2,2,2-tetrachloroethyl)pyridinium chloride (43). Tlie synthesis of 43 follows the standard three-component reaction. Tliionyl chloride, trichloroacetaldehyde, and pyridine were reacted at 0°C in MeCN to give this salt in excellent yield (Scheme 31). 

B) Preparation of 2-(Hydroxyiminomethyl)-1-Methyl Pyridinium Chloride An aqueous solution of 15 ml of 1-methyl-2-picolinium chloride having a concentration of 477 mg/ml Is covered with 50 ml of benzene in an atmosphere of nitrogen and cooled to below 10°C. An aqueous solution of sodium hydroxide is added dropwise and the mixture is stirred for 5 minutes and allowed to stratify. The aqueous phase Is then drawn off and the benzene solution is added slowly to a solution of 3 ml of nitrosyl chloride in 175 ml of benzene containing 0.5 ml of dimethyl formamide at about 10°C in an atmosphere of nitrogen with good agitation. The mixture is then stirred for 1.5 hours and then extracted with four... 

After evaporation of the solvent, the solid residue consists of 5-(2-chlorobenzyl)-thieno[3,2-cl -pyridinium chloride which melts at 166°C (derivative n°30). This compound is taken up into a solution comprising ethanol (300 ml) and water (100 ml). Sodium borohydride (NaBH4) (20 g) is added portionwise to the solution maintained at room temperature. The reaction medium is maintained under constant stirring during 1 2 hours and is then evaporated. The residue is taken up into water and made acidic with concentrated hydrochloric acid to destroy the excess reducing agent. The mixture is then made alkaline with ammonia and extracted with ether. The ether solution is washed with water, dried and evaporated. The oily residue is dissolved in isopropanol (50 ml) and hydrochloric acid in ethanol solution is then added thereto. 

In pyridinium chloride ionic liquids and in l,2-dimethyl-3-hexylimida2olium chloride ([HMMIMjCl), where the C(2) position is protected by a methyl group, only [PdClJ was observed, whereas in [HMIMjCl, the EXAFS showed the formation of a bis-carbene complex. In the presence of triphenylphosphine, Pd-P coordination was observed in all ionic liquids except where the carbene complex was formed. During the Heck reaction, the formation of palladium was found to be quicker than in the absence of reagents. Overall, the EXAFS showed the presence of small palladium clusters of approximately 1 nm diameter formed in solution. 

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