Several 1-alkoxymethyl-3-substituted-pyridinium chlorides with alkoxy chains including from 3 to 18 carbon atoms were prepared by the reaction of 3-substituted-pyridine with chloromethyl alkyl ethers. The prepared chlorides were examined for their antielectrostatic effects and their antimicrobial activities. 1-Dodecyloxymethyl-3-dimethylaminopyridinium chloride (23) exhibited strong antimicrobial activity and a wide antimicrobial spectrum, similar to the activity of benzalkonium chloride. We synthesized 1-alkoxymethyl-3-hydroxypyridinium chlorides possessing antielectrostatic properties, but lacking antimicrobial activity. The antielectrostatic effect and antimicrobial activities are strongly dependent on the kind of substituent at the 3-position in the pyridine ring and are greatly affected by an alkoxy chain. It was shown that dimethylamino group in position three must be present for a high antielectrostatic and antimicrobial activity of the agent.Paper no. S1318 in JSD 6, 119-123 (April 2003).KEY WORDS: Antielectrostatic effect, antimicrobial activity, pyridinium chlorides.Compounds containing the pyridinium moiety attached to heterocyclic systems are important in both biological and organic synthesis. Applications of pyridinium salts deserve considerable attention as phase transfer catalysts (1), biocides with a wide antimicrobial spectrum (2-7), cationic surfactants, and a potential new solvent-ionic liquid for synthesis and catalysis (8-12). Microbes easily become resistant to pyridinium salts. Modification of the structure of the salts transiently eliminates the effect. Nevertheless, the need persists to search continually for new, effective compounds. Pyridinium salts can be utilized as acylating agents (13). Especially effective are acylation reactions proceeding via quaternary 4-dimethylaminopyridinium salts, so-called "super nucleophiles." Furthermore, pyridinium compounds can interact with many polar and even some nonpolar functional groups. They promote esterification of terephthalic acid (14) and are powerful crystal growth inhibitors in liquors containing plant organics (15). 1-Decylpyridinium, 1-decyl-3-hydroxypyridinium, and 1-decyl-3-carboxypyridinium bromides exhibit high corrosion-resistance properties with steel (16) through a physical adsorption on the surface. The adsorption itself obeys the Langmuir adsorption isotherm.The aim of this paper is to elucidate the antielectrostatic and antimicrobial properties of 1-alkoxymethyl-3-substituted-pyridinium chlorides having alkoxy chains including from 3 to 18 carbon atoms. EXPERIMENTAL PROCEDURESElemental analyses were performed at the University of A. Mickiewicz, Poznań, Poland. Satisfactory elemental analyses of CHN for all chlorides were acquired with 0.32% tolerance between the calculated and experimental values. 1 H Nuclear magnetic resonance (NMR) spectra were recorded with a Varian model XL 300 spectrometer at 300 MHz with tetramethylsilane as the standard, and 13 C NMR spectra were recorded on the same instrument at 75 MHz.Chloromethyl alk...
The reaction of ozone with a number of pyridinium salts containing 1-alkoxymethyl and 1-alkylthiomethyl substituents was determined at a total substrate concentration of 2 g/L. Ozonation of pyridinium salts was strongly dependent on the kinds and positions of the substituents in the pyridine ring. The most favorable were the third position and the substituents including hydroxyl or dimethylamino groups. In an aqueous solution, 1-(alkoxymethyl)-3hydroxypyridinium, 1-(alkylthiomethyl)-3-hydroxypyridinium, and 1-(alkoxymethyl)-3-(dimethylamino)pyridinium salts reacted with ozone. The reaction was fast, and pyridinium salts were quantitatively removed. 1-(Alkoxymethyl)-and 1-(alkylthiomethyl)pyridinium chlorides were obtained by the Menschutkin reaction. In general, the procedure was simple and the reaction was productive and short. During the course of this study, we synthesized a new generation of cationic surfactants that were extremely reactive with ozone in an aqueous solution.
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