Synthesis of an active quaternary phosphonium salt and its application to the Wittig reaction: Kinetic study

Wang, Maw‐Ling; Liu, Biing-Lang; Lin, Shan-Je

doi:10.1016/j.jcice.2007.08.005

Cited by 9 publications

(3 citation statements)

References 19 publications

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“…The substituted benzimidazolin-2-thione was prepared from 4-substituted-1,2-diaminobenzene by heating with carbon disulfide, potassium hydroxide in ethanolmethod described by Wang et al [20] . The 5 th position was substituted by -CH3, -OCH3, -Cl and -Br groups to enhance the antiinflammatory activity of benzimidazolin-2-thione analogues.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Ganji¹,

Agrawal²

2020

ijps

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Ganji and Agrawal: Antiinflammatory Activity of Piperazine DerivativesBenzimidazole-2-thione derivatives are known to possess broad spectrum of biological activities, and the most prominent being the antiinflammatory activity. The synthesis of these compounds involve three steps, William's reaction of 5(6)-(un)-substituted-1H-benzimidazol-2-thiols with chloroacetic acid in presence of sodium hydroxide and refluxing, which was further reacted with acetic anhydride in pyridine medium on a steam bath followed by hydrolysis with a N-mono substituted piperazine in ethanol medium under reflux conditions to get 5(6)-(un)-substituted(1H-benzimidazol-2-yl-thio)acetyl piperazine derivatives. Molecular docking experiments were carried out against cox-2 enzyme using GOLD software 5.1.0. Docking studies revealed important binding interactions of synthesized derivatives with cox-2 enzyme indicating nonselective interactions, which were in agreement with the in vivo antiinflammatory activity. Absorption, distribution, metabolism, and excretion properties of the synthesized derivatives were determined by QikProp. These derivatives were tested in the carrageenan-induced rat paw oedema model to determine the antiinflammatory activity.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Ganji¹,

Agrawal²

2020

ijps

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“…The most commonly encountered phosphonium compounds have four organic substituents attached to a phosphorus center, forming the quaternary phosphonium cation. Along with a multitude of available anions, salts of these quaternary compounds are extensively used as Wittig reagents [1], phase transfer catalysts in asymmetric synthesis [2][3][4][5][6], ionic liquids [7][8][9], corrosion inhibitors [10], and polymer-based anion exchange membranes [11,12], as well as tracers for tumor imaging [13]. The versatility of the phosphonium quaternary compounds is known to be contributed by the different molecular features and self-organization of the ions within the compound.…”

Section: Introductionmentioning

confidence: 99%

Interplay of Ionic Species in Salts of Homoleptic Quaternary Phosphonium Cations Bearing Linear Biphenyl Moieties

et al. 2022

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Quaternary phosphonium salts are popular candidates used in many chemical transformations and synthetic chemistry, notably in catalysis. We have examined the single crystals of two bulky phosphonium compounds, tetra([1,1′-biphenyl]-4-yl) phosphonium dicyanamide (C48H36P+·N(CN)2−, compound 1), and tetra([1,1′-biphenyl]-4-yl) phosphonium bromide hydrate (C48H36P+·Br−, CH3CN, H2O, compound 2), and herein report the structural properties for the compounds with an emphasis on the influence of the ion-ion interaction towards self-assembly; the overall self-assembly for both structures is very similar, with subtle differences in the cell parameters. The symmetrical tetra ([1,1′-biphenyl]-4-yl) phosphonium cations in both compounds self-assembled to form robust stacked columns in the solid-state, with voids occupied by anions or solvent molecules. Quantitative examination of intermolecular interactions using Hirshfeld surface analysis found that classical and non-classical hydrogen bonding appears to be the dominant contributor in stabilizing the self-assembly in both cases. The present work can not only benefit in understanding the mutual interaction between the sterically encumbered tetra ([1,1′-biphenyl]-4-yl) phosphonium cations and between counterions, but also provide insights for the self-assembled arrays in the solid-state.

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“…Both quaternary ammonium salts and quaternary phosphonium salts, which possess analogous molecular structures (they can be formulated as ((NR 4 ) + L − ) and ((PR 4 ) + L − ), respectively, R groups may be the same or different alkyl or aryl group, L − is halide ion), have been widely used within the fields of antimicrobial, catalysis, and surface modification due to their good chemical stability and excellent electrical properties [23][24][25]. In the field of mineral processing, there are also intense investigations on flotation of quartz from iron ore using quaternary ammonium salts collectors [26].…”

Section: Introductionmentioning

confidence: 99%

Discovery of a Novel Cationic Surfactant: Tributyltetradecyl-Phosphonium Chloride for Iron Ore Flotation: From Prediction to Experimental Verification

Pan

Gao

et al. 2017

Minerals

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Abstract:In this work, tributyltetradecyl-phosphonium chloride (TTPC), has been first introduced to be a novel and efficient cationic surfactant for cationic reverse flotation separation of quartz from magnetite. The first-principles density functional theory calculations, Zeta potential measurements and adsorption isotherm measurements consistently predict that TTPC may be a promising collector that is better than dodecyl triethyl ammonium chloride (DTAC), based on the facts that TTPC and DTAC both prefer to physically adsorb on the quartz surface owing to electrostatic force, but the active part (P + (C 4 H 9 ) 3 ) of TTPC takes much more positive charges than that (N + (CH 3 ) 3 ) of DTAC. The micro-flotation and Bench-scale flotation results further verify that TTPC presents a stronger collecting power and much better selectivity for iron ore reverse flotation in comparison to the conventional collector DTAC. Furthermore, the corresponding adsorption mechanism of TTPC on the quartz have also been investigated in detail. This work might show a good example to discover a potential candidate collector by analogy with a known excellent collector based on reasonable prediction.

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Synthesis of an active quaternary phosphonium salt and its application to the Wittig reaction: Kinetic study

Cited by 9 publications

References 19 publications

Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Interplay of Ionic Species in Salts of Homoleptic Quaternary Phosphonium Cations Bearing Linear Biphenyl Moieties

Discovery of a Novel Cationic Surfactant: Tributyltetradecyl-Phosphonium Chloride for Iron Ore Flotation: From Prediction to Experimental Verification

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