Proof of ion-pair structures in ammonium-based protic ionic liquids using combined NMR and DFT/PCM-based chemical shift calculations.

The self-assembly of triethylammonium bis(trifluoromethylsulfonyl)imide, i.e. [(C2H5)3NH][TFSI], in chloroform and aqueous solutions has been investigated using 1H NMR spectroscopy and computational (DFT/PCM prediction) methods. We have examined a number of ion pairs formed between the [(C2H5)3NH]+ cation with different conformations of alkyl substituents as well as various dispositions of the multi-site [TFSI]- anion. Based on the agreement between the calculated (DFT) and observed 1H NMR chemical shifts, [(C2H5)3NH][TFSI] in chloroform formed lipophilic complexes with effective N+-HN or N+-HO hydrogen bonding, whereas hydrophilic complexes with Cα-HO and Cα-HF hydrogen bonding are found in aqueous solutions. This study provides a new insight into the self-aggregation of ammonium PILs incorporating the widely used [TFSI]- anion and demonstrates the importance of solvent effects on chemical shifts. The simulations with explicit and implicit dielectric continuum solvents are found to be the most realistic method, yielding a representative ensemble of structures.

Influence of oligomeric herbicidal ionic liquids with MCPA and Dicamba anions on the community structure of autochthonic bacteria present in agricultural soil.

The aim of this study was to evaluate the impact of selected herbicidal ionic liquids (HILs), which exhibit high efficacy in terms of weed control and low toxicity, but may be persistent due to limited biodegradability, on the community structure of autochthonic bacteria present in agricultural soil. Four different oligomeric HILs (with two types of cations and different ratio of herbicidal anions) were synthesized and characterized by employing (1)H and (13)C NMR. The results of biodegradation assay indicated that none of the tested HILs could be classified as readily biodegradable (biodegradation rate ranged from 0 to 7%). The conducted field studies confirmed that the herbicidal efficacy of the HILs was higher compared to the reference herbicide mixture by 10 to 30%, depending on the dose and weed species. After termination of field studies, the soil treated with the tested HILs was subjected to next generation sequencing in order to investigate the potential changes in the bacterial community structure. Proteobacteria was the dominant phylum in all studied samples. Treatment with the studied HILs resulted in an increase of Actinobacteria compared to the reference herbicidal mixture. Differenced among the studied HILs were generally associated with a significantly higher abundance of Bacteroidetes in case of 1-HIL-Dicamba 1/3 and Firmicutes in case of 2-HIL-Dicamba 1/3.

Synthesis and antimicrobial activities of new pyridinium and benzimidazolium chlorides.

A novel class of pyridinium and benzimidazolium chloride has been obtained in high yield. The antimicrobial activities of three homologous series of pyridinium and benzimidazolium chlorides against cocci, rods, fungi and bacillus have been measured. The antimicrobial activities of N,N'-bis[3-(1-alkoxymethyl)pyridinium chloride]methylenediamines, 1-undecyloxymethyl-3-(1-benzimidazolmethylamino)pyridinium, 1-undecyloxymethyl- and 1-dodecyloxymethyl-3-[1(benzotriazol-1-yl)methylamino]pyridinium chlorides exhibited strong activity and wide antibacterial spectra similar to the activity of benzalkonium chloride.

Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group.

A novel class of functionalized cationic surfactant has been obtained. The work-up procedure of synthesis is very simple, the yield is high and the pyridinium salts with alkoxymethyl hydrophobic group are easily purified. All the salts examined showed anti-microbial activities. Some of them exhibited strong activity and wide anti-bacterial spectra similar to the activity of benzalkonium chloride. The relationship between chemical structure and anti-microbial activity was analysed by the QSAR method.

Influence of counterions on the interaction of pyridinium salts with model membranes.

The interaction of pyridinium salts (PS) with red blood cells and planar lipid membranes was studied. The aim of the work was to find whether certain cationic surfactant counterion influence its possible biological activity. The counterions studied were Cl-, Br-, I-, ClO4-, BF4- and NO3-. The model membranes used were erythrocyte and planar lipid membranes (BLM). At high concentration the salts caused 100% erythrocyte hemolysis (C100) or broke BLMs (CC). Both parameters describe mechanical properties of model membranes. It was found that the efficiency of the surfactant to destabilize model membranes depended to some degree on its counterion. In both, erythrocyte and BLM experiments, the highest efficiency was observed for Br-, the lowest for NO3-. The influence of all other anions on surfactant efficiency changed between these two extremities; that of chloride and perchlorate ions was similar. Some differences were found in the case of BF4- ion. Its influence on hemolytic possibilities of PS was significant while BLM destruction required relatively high concentration of this anion. Apparently, the influence of various anions on the destructive action of PS on the model membrane used may be attributed to different mobilities and radii of hydrated ions and hence, to different possibilities of particular anions to modify the surface potential of model membranes. This can lead to a differentiated interaction of PS with modified bilayers. Moreover, the effect of anions on the water structure must be taken into account. It is important whether the anions can be classified as water ordering kosmotropes that hold the first hydration shell tightly or water disordering chaotropes that hold water molecules in that shell loosely.

[Bactericidal properties of copper (II) complexes with 1-alkylimidazole]. / Przeciwbakteryjna aktywnosc kompleksów miedzi (II) z 1-alkiloimidazolem.

The copper(II) complexes with 1-alkylimidazole were prepared. Bactericidal properties of the obtained complexes against Staphylococcus aureus, Micrococcus luteus and Pseudomonas aeruginosa were studied. Particularly high activity against microbial strains was shown by complex [Cu(1-C4H9Im)4(CIO4)2].

Synthesis and antimicrobial activity of new 1-benzylbenzimidazolium chlorides.

1-Benzylbenzimidazole reacts with chloromethylalkyl ethers or sulfides or chloromethylcycloalkyl ethers to produce 3-alkoxymethyl-1-benzylbenzimidazolium or 3-alkylthiomethyl-1-benzylbenzimidazolium or 1-benzyl-3-cycloalkoxymethylbenzimidazolium chlorides in very good yields. All the 1-benzylbenimidazolium chlorides showed antimicrobial activity. The relationship between chemical structure and antimicrobial activity was analyzed by quantitative structure-activity relationships (QSAR).

Synthesis and antimicrobial activity of new quaternary ammonium chlorides.

Decyldimethylamine reacts readily with chloromethylalkyl ethers of sulfides, chloromethylbenzyl ethers or sulfides and chloromethylcycloalkyl ethers to give quaternary ammonium chlorides in very good yields. All the chlorides studied showed antimicrobial activity. The relationship between the chemical structure and antimicrobial activity was analyzed by rough sets.

Quantitative relation between surface active properties and antibiotic activity of 1-alkyl-3-alkylthiomethylimidazolium chlorides.

The critical micelle concentration (CMC) values were determined by surface tensiometry, and the hydrophobicity index (HI) was calculated. The quantitative relation between the minimum inhibitory concentration (MIC) and the CMC, and the HI was calculated.

Synthesis and antibiotic activity of 1-cycloalkoxymethyl-4-dimethylaminopyridinium and 1-[(1-alkoxy)ethyl]-4-dimethylaminopyridinium chlorides.

DMAP reacts readily with chloromethylcycloalkyl ethers and alpha-chloroethyl alkyl ethers to give stable (1a-1e) and unstable (2a-2h) pyridinium chlorides. Reaction of these chlorides with NaOH produces the corresponding 4-pyridones. All the chlorides synthesized showed antibiotic activity. Particularly high activity against microbes representing cocci, rods, fungi, and bacilli was shown by 1-cyclododecyloxymethyl-4-dimethylaminopyridinium chloride 1d and 1-[(1-dodecyloxy)ethyl]-4-dimethylaminopyridinium chloride 2f.

[Actions of new iminium compounds against bacteria and fungi. 30. 3-alkoxymethyl-1-hexyl-, 3-alkylthiomethyl-1-hexyl-, 3-alkoxymethyl-1-octyl- and 3-alkylthiomethyl-1-octylbenzimidazolium chlorides]. / Wirkung neuer Iminiumverbindungen gegen Bakterien und Pilze, 30. Mitt.: 3-Alkoxymethyl-1-hexyl-,3-Alkylthiomethyl-1-hexyl-, 3-Alkoxymethyl-1-oktyl- und 3-Alkylthiomethyl-1-oktylbenzimidazoliumchloride.

Syntheses and antimicrobial activity of the title compounds are described. They were obtained by reaction of 1-hexyl- or 1-octylbenzimidazol with chloromethylalkyl ether or chloromethylalkyl sulfide. The antibacterial properties were tested on 13 strains of bacteria and fungi. The best antibacterial activity was exhibited by chlorides with octylthiomethyl and decyloxymethyl groups.

[Iminium compounds against bacteria and fungi. 29. 3-Alkoxymethyl-1-ethyl-, 3-alkylthiomethyl-1-ethyl-, 3-alkoxymethyl-1-butyl-, and 3-alkylthiomethyl-1-butylbenzimidazolium chloride]. / Iminiumverbindungen gegen Bakterien und Pilze, 29. Mitt.: 3-Alkoxymethyl-1-ethyl-, 3-Alkylthiomethyl-1-ethyl-, 3-Alkoxymethyl-1-butyl- und 3-Alkylthiomethyl-1-butylbenzimidazolium-chloride.

Syntheses and antimicrobial activity of 3-alkoxymethyl-1-ethyl-, 3-alkylthiomethyl-1-ethyl-, 3-alkoxymethyl-1-butyl-, and 3-alkylthiomethyl-1-butylbenzimidazolium chlorides are described. The compounds were obtained by reaction of 1-ethyl- or 1-butylbenzimidazole with chloromethylalkyl ethers or chloromethylalkyl sulfide. Antibacterial properties were tested on 13 strains of bacteria and fungi. 3-Dodecylthio-methyl-1-ethyl-benzimidazolium chloride exhibited the highest antibacterial activity.

[Activity of new iminium compounds against bacteria and fungi. 28. Synthesis of 1-ethyl-, 1-n-dodecyl-2-phenyl-3-(n-alkylthiomethyl)- and 1-ethyl-, 1-n-dodecyl-2-phenyl-3-(n-alkoxymethyl)imidazolium chlorides]. / Wirkung neuer Iminiumverbindungen agen Bakterien und Pilze. 28. Mitteilung: Synthese von 1-ethyl-, 1-n-dodecyl-2-phenyl-3-(n-alkylthiomethyl)- und 1-ethyl-, 1-n-dodecyl-2-phenyl-3-(n-alkoxymethyl)imidazolimchloriden.

The synthesis of quaternary imidazolium compounds was performed by reaction of 1-ethyl- or 1-n-dodecyl-2-phenylimidazole with chloromethyl-n-alkyl ether or chloromethyl-n-alkyl sulfid. The antibacterial properties of the compounds obtained were tested on 13 strains of bacteria and fungi. 1-Ethyl-2-phenyl-3-(n-decylthiomethyl)-, 1-ethyl-2-phenyl-3-(n-dodecylthiomethyl)imidazolium chloride and 1-n-dodecyl-2-phenyl-3-(n-butylthiomethyl)-, 1-n-dodecyl-2-phenyl-3-(n-hexylthiomethyl)imidazolium chloride indicated the best antibacterial activity.

[Actions of new iminium compounds on bacteria and fungi. 27. Synthesis of 1-n-decyl-2-phenyl-3-(n-alkylthiomethyl)- and 1-n-decyl-2-phenyl-3-(n-alkoxymethyl)imidazolium chlorides]. / Wirkung neuer Iminiumverbindungen gegen Bakterien und Pilze, 27. Synthese von 1-n-decyl-2-phenyl-3-(n-alkylthiomethyl)- und 1-n-decyl-2-phenyl-3-(n-alkoxymethyl)imidazoliumchloriden.

The imidazolium compounds 1-3 were prepared by quaternization of 1-decyl-2-phenylimidazole with the pertinent chloromethyl-n-alkyl ethers. 1-3 were tested for their antibacterial and antimycotic efficacies.

[Investigation of activity of new quaternary imidazole-linear chlorides against selected bacterial strains. Synthesis of 2-alkyl-3-alkymethyl-1-ethylimidazolelinear and 2-alkyl-3-alkoxymethyl-1-ethylimidazolelinear chlorides]. / Badanie aktywnosci nowych czwartorzedowych chlorków imidazoliniowych wobec wybranych szczepów bakterii. Synteza chlorków 2-alkilo-3-alkilotiometylo-1-etyloimidazoliniowych i 2-alkilo-3- alkokosymetylo-1-etyloimidazolinowych.

Synthesis and bacteriostatic properties of a new alkylthiomethylimidazole-linear and alkomethyly-limidazole-linear chlorides was described. It was found that these chlorides are active against bacilli, cocci and yeast-like fungi and express lower activity against rods. Highest activity was observed with 2-benzyl-3-decyloxymethyl-1--ethylimidazolinear and 1-ethyl-heptadecyl-3-undecyloxymethylimidazolelinear chlorides.

Synthesis and bactericidal properties of pyridinium chlorides with alkylthiomethyl and alkoxymethyl hydrophobic groups.

The products of a reaction between 3-ethoxymethylpyridine and chloromethylalkyl ether or sulfide were proven to be 1-[(alkylthio)-methyl]-3-[(ethoxy)methyl]pyridinium or 1-[(alkoxy)methyl]-3-[(ethoxy)-methyl]pyridinium chlorides. Bacteriostatic properties of the obtained chlorides against 13 different microbial strains representing cocci, rods, fungi, and bacilli were studied. The MICs were measured by serial dilution. All studied chlorides showed bacteriostatic properties. Particularly high activity against microbes was shown by 1-[(dodecylthio)-methyl]-3-[(ethoxy)methyl]pyridinium and 3-[(ethoxy)methyl]-1-[(tetradecylthio)methyl]pyridinium chlorides.

[Synthesis and action of 1-n-hexyl-2-phenyl-3-(n-alkoxymethyl)- and 1-n-hexyl-2-phenyl-3-(6-n-alkylthiomethyl)imidazolium chlorides]. / Synthese und Wirkung von 1-n-Hexyl-2-phenyl-3-(n-alkoxymethyl)-und 1-n-Hexyl-2-phenyl-3-(n-alkylthiomethyl)imidazoliumchloriden.

The synthesis of quaternary imidazolium chlorides was performed by reaction of 1-n-hexyl-2-phenyl-imidazole with chloromethylalkyl ether or chlormethylalkyl sulfide. The antibacterial properties of the compounds obtained was tested on 13 strains of bacteria and fungi. Chlorides with octyl- and decylthiomethyl moiety indicated the best antibacterial activity.

[Antimicrobial action of new imidazolinium compounds]. / Antimikrobielle Wirkung neuer Imidazoliniumverbindungen.

Syntheses and antibacterial activity of 1-ethyl-2-alkyl-3-(alkoxymethyl)- and 1-ethyl-2-alkyl-3-(alkylthiomethyl)imidazolinium chlorides are described. Syntheses of the imidazolinium compounds were performed by reaction of 1-ethyl-2-alkylimidazoline with chloromethylalkyl ether or with chloromethylalkyl sulfide. Antimicrobial properties of obtained compounds was tested on 13 strains of bacteria and fungi. Chlorides with alkylthiomethyl residue showed the highest antimicrobial activity.