Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(−)-menthoxymethyl substituent

Pernak, Juliusz; Feder‐Kubis, Joanna; Cieniecka‐Rosłonkiewicz, Anna; Fischmeister, Cédric; Griffin, Scott T.; Rogers, Robin D.

doi:10.1039/b616215k

Cited by 81 publications

(89 citation statements)

References 31 publications

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“…The synthesized salts were characterized by 1 H NMR and 13 C NMR. The obtained results were consistent with the results presented earlier [12]. …”

Section: Chemicalssupporting

confidence: 83%

“…Bacteriostatic and fungistatic activity as well as bactericidal and fungicidal properties of the chiral ionic liquids described, have been studied previously [13]. Moreover, imidazolium salts exhibit excellent antistatic properties regardless of the alkyl chain length [12].…”

Section: Introductionmentioning

confidence: 98%

“…Detailed description of the preparation and physicochemical properties of the obtained chiral ionic liquids are described in the previous publication [12]. The synthesized salts were characterized by 1 H NMR and 13 C NMR.…”

Section: Chemicalsmentioning

confidence: 99%

“…This group includes ammonium compounds, pyridinium, alkylimidazoline, alkoxymethylimidazoline compounds and symmetrical imidazolium salts with various anions [12]. Among the chiral ionic liquids (CILs), a particularly interesting group are 3-alkyl-1-[(1R,2S,5R)-(−)-menthoxymethyl]imidazolium chlorides.…”

Section: Introductionmentioning

confidence: 99%

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The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

Biczak

Pawłowska

Feder‐Kubis

2017

Ecological Chemistry and Engineering S

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Weeds constitute a huge group of undesirable plants, widespread throughout the world. They represent a big problem for most farmers, who implement different methods to fight against them. Thanks to their wide occurrence, weeds however, can be an excellent indicator of the quality of soil and the whole environment where they are present. In this paper, we present the impact of four alkylimidazolium chlorides with a natural terpene component introduced into the soil: (1R,2S,5R)-(-)-menthol and alkyl substituents containing 1, 4, 9 or 12 carbon atoms, on the growth and development of selected weed species. Compounds with the highest phytotoxic activity towards gallant soldier, white goosefoot and common sorrel were chlorides with methyl and butyl substituents, while compounds with nonyl and dodecyl substituents demonstrated a weak effect on these weeds. Phytotoxicity of the salts tested was largely dependent on the applied concentration of the compound and the genetic make-up of plant species used in the experiment. This was reflected in the inhibition of plants' length and their roots, as well as changes in the content of dry matter and photosynthetic pigments.

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“…The synthesized salts were characterized by 1 H NMR and 13 C NMR. The obtained results were consistent with the results presented earlier [12]. …”

Section: Chemicalssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 98%

Section: Chemicalsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

Biczak

Pawłowska

Feder‐Kubis

2017

Ecological Chemistry and Engineering S

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“…Yet the most important feature of ionic liquids is that they provide the possibility of obtaining substances of optimal properties for a given process through the modification of the cation structure and selection of the appropriate anion; therefore, the term designer solvents has been invented for these salts. The unique properties of ionic liquids may bring about a wide range of applications of these substances in all areas of the chemical industry, including catalysis, extraction, synthesis, as well as the pharmaceutical and food industries and electrochemistry and biotechnology [2,[9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Comparison of Phytotoxicity of Selected Phosphonium Ionic Liquid

Biczak

Bałczewski

Pawłowska

et al. 2014

Ecological Chemistry and Engineering S

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Ionic liquids have attracted considerable interest in various areas as new, non-volatile and nonflammable organic solvents, catalysts, reaction additives, ligands, drugs and other dedicated materials etc. Their general use, sometimes in bulky quantities, requires determination of their potential ecotoxicity on selected organisms. In the present work, influence of triphenylmethylphosphonium iodide (1) and triphenylhexadecylphosphonium iodide (2), introduced to soil, on germination and early stages of growth and development of superior plants was investigated using the plant growth test based on the OECD/OCDE 208/2006. In this test, the seeds of selected species, i.e. land superior plants -spring barley (Hordeum vulgare) and common radish (Raphanus sativus L. subvar. radicula Pers.) were planted in pots containing soil to which a test chemical compound had been added and in pots with control soil. To evaluate the phytotoxicity of ionic liquids 1 and 2 germination and weight (dry and fresh) of control plant seedlings were determined and compared with the germination and weight (dry and fresh) of the seedlings of plants grown in the soil watered with appropriate amounts of the test chemicals. The visual assessment of any types of damage to the test species, such as growth inhibition, chlorosis and necrosis, was also carried out and documented by digital photographs. Based on the obtained results, magnitudes of the LOEC -the lowest concentration causing observable effects in the form of reduction in growth and germination compared with the control and the NOEC -the highest concentration not causing observable, toxic effects -were also determined.

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New palladium(II)–N‐heterocyclic carbene complexes containing benzimidazole‐2‐ylidene ligand derived from menthol: synthesis, characterization and catalytic activities

Kılınçarslan

Günay

Fırıncı

et al. 2016

Applied Organom Chemis

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A new series of sterically hindered ligands containing (1R,2S,4R)-(+)-menthoxymethyl group attached to benzimidazole-based Nheterocyclic carbene (NHC), palladium-bis-NHC complexes and (κ 2 -C,N)-palladacyclic NHC complexes have been synthesized and characterized using appropriate spectroscopic techniques. Catalytic performance of the palladium complexes has been investigated for allylic alkylation, Suzuki and Heck carbon-carbon coupling reactions. These complexes smoothly catalyse the carboncarbon bond formation reactions.

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Synthesis and properties of chiral imidazolium ionic liquids with a (1R,2S,5R)-(−)-menthoxymethyl substituent

Cited by 81 publications

References 31 publications

The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

The Effect of Ionic Liquids With (–)-Menthol Derivative Containing a Chloride Anion to Weed

Comparison of Phytotoxicity of Selected Phosphonium Ionic Liquid

New palladium(II)–N‐heterocyclic carbene complexes containing benzimidazole‐2‐ylidene ligand derived from menthol: synthesis, characterization and catalytic activities

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