Naturally based ionic liquids with indole-3-acetate anions and cations derived from cinchona alkaloids

Rzemieniecki, Tomasz; Kleiber, Tomasz; Pernak, Juliusz

doi:10.1039/d1ra04805h

Cited by 6 publications

(4 citation statements)

References 64 publications

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“…Following recent reports of biologically active ionic liquids (ILs) based on natural compounds and indole-3-butyric acid-based salts, ,, we focused on the synthesis of novel dicationic ionic liquids (DILs) with the IBA anion. Knowing that IBA is poorly soluble in water and that an adjuvant is required to improve the wetting properties and solubility, we used a bis-ammonium cation with two long hydrophobic alkyl chains to obtain compounds with the desired properties.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, it has been confirmed that the conversion of IBA or IAA to their ionic forms results in these compounds having increased biological activity. 11 Interestingly, introducing a bis-ammonium cation can result in a significantly beneficial modification of physicochemical properties and biological activity than monocationic analogues.…”

Section: ■ Introductionmentioning

confidence: 99%

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Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Kaczmarek,

Pacholak,

Burlaga

et al. 2023

ACS Sustainable Chem. Eng.

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Due to the poor water solubility of indole-3-butyric acid (IBA), adding appropriate adjuvants to this compound during application is essential. The physicochemical properties of plant growth regulators can be easily modified by transforming them into ionic liquids. In this research, IBA was converted into an anion and conjugated with a bis-ammonium cation to form novel dicationic ionic liquids (DILs). The purpose of obtaining these new DILs was to improve the biological activity and determine the effects of the modifications on the stability and persistence of soil microorganisms. The synthesis method enabled the designed DILs to be obtained with yields above 85%. The surface tension and chemical stability results indicated that these properties could be optimized by selecting appropriate cations. A solubility study indicated that the transformation of IBA into DILs improved the solubility of the active ingredient in water. Analysis of the growth-stimulating activity of the DILs on corn showed that the application of DILs significantly increased the fresh and dry cobs' weight compared to control plants. An experiment evaluating the effects of DILs on soil microorganisms showed that high concentrations of IBA anion inhibited bacterial growth and could have distorted cell metabolism. The DILs presented in this research may be potential alternatives to commercially used formulations.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Kaczmarek,

Pacholak,

Burlaga

et al. 2023

ACS Sustainable Chem. Eng.

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“…The preparation of ionic liquids bearing a quinine (222a-f, Scheme 39) or a quinidine moiety (224) and (1Hindol-3-yl)acetic acid (indole-3-acetic acid), a naturally occurring plant growth hormone, was reported by Pernak and co-workers in 2021. 90 The readily available quinine 218, a well-known antimalarial cinchona alkaloid, was selectively N-alkylated with six n-alkyl bromides (2-12 carbon atom chains) in DMSO as reported in their previous article. 91 Then, the bromide in salts 219a-f was replaced by the OH anion by means of an ion-exchange resin and the resulting bases 220a-f were neutralized with commercially available indole-3-acetic acid (221) to afford the new ILs 222a-f. Ionic liquid 224 (Scheme 39) containing an N-ethylammonium cation and the same carboxylate anion was also synthesized starting from quinidine 223, another cinchona alkaloid.…”

Section: Miscellaneous Ionic Liquidsmentioning

confidence: 99%

“…Unfortunately, for all the synthetic steps described above, the isolated yields were not reported. The seven ILs were found 90 able to stimulate the growth and development of lettuce ( Lactuca sativa ) as a control plant when compared to pure acid 221 or equimolar mixtures of 221 and quinine 218 . Beside the absence of phytotoxic effects, it was also proven that these ILs were harmless toward several model microorganisms present in the environment.…”

Section: Miscellaneous Ionic Liquidsmentioning

confidence: 99%

Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products

Ranjbar-Karimi,

Marra,

Khorasani

2024

Synthesis

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Ionic liquids, nonvolatile salts featuring a melting point below 100 °C, are one of the few alternative solvents for environmentally friendly processes. However, like most molecular solvents, they are usually prepared by means of building blocks derived from fossil oil. Fortunately, an increasing number of ionic liquids are synthesized starting from renewable natural products such as sugars and amino acids. In the present review, we describe the detailed synthesis and applications of the biosourced ionic liquids reported in the literature over the last four years.1 Introduction2 Carbohydrate-Based Ionic Liquids3 Amino Acid Based Ionic Liquids4 Terpene-Based Ionic Liquids5 Miscellaneous Ionic Liquids6 Conclusion

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Asymmetric Suzuki Cross‐Coupling Reactions Catalyzed by Chiral Surfactant‐Stabilized Palladium Nanoparticles

2022

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We report the synthesis of cinchonine and hydrocinchonine derived surfactants by reacting with various mono alkylating agents (hexyl, octyl, octadecyl, dodecyl bromides) and di-alkylating agent such as α,α'-p-xylene-dibromide. A series of chiral surfactants have been used to stabilize palladium nanoparticles (NPs) which are water soluble. These Pd NPs were utilized in asymmetric Suzuki cross coupling reaction of naphthalene boronic acids with substituted naphthalene bromides to get binaphthalenes and terephenylenes. It was observed that, the surfactant's alkylchain length and the palladium source played a major role in this catalytic reaction. The high solubility and positive zeta potential of gemini-surfactant (GS) stabilized Pd NPs make them attractive as a potential candidate for the synthesis of binaphthalenes and terephenylenes with high yields.

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Naturally based ionic liquids with indole-3-acetate anions and cations derived from cinchona alkaloids

Abstract: The transformation of a plant hormone into an alkaloid-based ionic liquid results in unique changes in physicochemical and biological properties.

Cited by 6 publications

References 64 publications

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products

Asymmetric Suzuki Cross‐Coupling Reactions Catalyzed by Chiral Surfactant‐Stabilized Palladium Nanoparticles

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