A simple synthesis of novel extraction reagents. 4-Acyl-5-pyrazolone-substituted crown ethers

Yamazaki, Shoko; Hanada, Miho; Yanase, Yuichiro; Fukumori, Chizue; Ogura, Kaoru; Saeki, Tohru; Umetani, Shigeo

doi:10.1039/a809589b

Cited by 20 publications

(7 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The extractants HPMBP (Tokyo Chemical Industry Co., >98.0%) and DBzDA18C6 (Aldrich Chemical Co., 97%) were used without further purification. The synthesis of H 2 βDA18C6 was performed according to published procedures. , The ILs [C n mim][Tf 2 N] ( n = 2, 4, and 6) were synthesized according to a published procedure , with several minor modifications. The precursors [C n mim][Br] were recrystallized from acetonitrile at least three times and subsequently treated with activated carbon.…”

Section: Methodsmentioning

confidence: 99%

Specific Cooperative Effect of a Macrocyclic Receptor for Metal Ion Transfer into an Ionic Liquid

et al. 2012

Self Cite

View full text Add to dashboard Cite

An intramolecular cooperative extraction system for the removal of strontium cations (Sr(2+)) from water by use of a novel macrocyclic receptor (H(2)βDA18C6) composed of diaza-18-crown-6 and two β-diketone fragments in ionic liquid (IL) is reported, together with X-ray spectroscopic characterization of the resulting extracted complexes in the IL and chloroform phases. The covalent attachment of two β-diketone fragments to a diazacrown ether resulted in a cooperative interaction within the receptor for Sr(2+) transfer, which remarkably enhanced the efficiency of Sr(2+) transfer relative to a mixed β-diketone and diazacrown system. The intramolecular cooperative effect was observed only in the IL extraction system, providing a 500-fold increase in extraction performance for Sr(2+) over chloroform. Slope analysis and potentiometric titration confirmed that identical extraction mechanisms operated in both the IL and chloroform systems. Extended X-ray absorption fine structure spectroscopy revealed that the average distance between Sr(2+) and O atoms in the Sr(2+) complex was shorter in IL than in chloroform. Consequently, Sr(2+) was held by H(2)βDA18C6 more rigidly in IL than in chloroform, representing an important factor dominating the magnitude of the intramolecular cooperative effect of H(2)βDA18C6 for Sr(2+). Furthermore, competitive extraction studies with alkaline earth metal ions revealed that the magnitude of the intramolecular cooperative effect depended on the suitability between metal ion size and the cavity size of H(2)βDA18C6. Sr(2+) was successfully recovered from IL by controlling the pH in the receiving phase, and the extraction performance of H(2)βDA18C6 in IL was maintained after five repeated uses.

show abstract

Section: Methodsmentioning

confidence: 99%

Specific Cooperative Effect of a Macrocyclic Receptor for Metal Ion Transfer into an Ionic Liquid

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…Acylpyrazolones are a compelling kind of β‐diketone compounds which are extensively used as solvent in extractions of metal ions, laser working materials and NMR shift‐reagents . Its Schiff base compounds have spectroscopic properties, antibacterial and antiviral activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and electrocatalytic behavior of a copper (II) complex derived from acylpyrazolone double Schiff bases

Zhang

et al. 2014

Crystal Research and Technology

View full text Add to dashboard Cite

A new double Schiff base complex, Cu(PMαFP) 2 en (HPMαFP = 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone, en = ethylenediamine), has been synthesized and characterized by elemental analysis, IR, UV, fluorescence spectra, thermal analysis, X-ray single crystal diffraction and cyclic voltammetry (CV). Its crystal structure is monoclinic with space group Pbca and cell parameters: a = 22.263(3)Å, b = 13.671(2)Å, c = 10.0920(16)Å, Z = 4, S = 1.028, R 1 = 0.0500 and wR 2 = 0.1285. It was found that the Cu 2+ ion is located in the coordination center. The Cu(II) has a slightly distorted plane quadrilateral coordination environment with two oxygen atoms and two nitrogen atoms of double Schiff base ligand in the equatorial plane. The complex has a one-dimensional chain supramolecular structure, which is connected by C-H ...N bonding interactions. In the electrochemical experiments, the CV curve displays an oxidation peak in the presence of uric acid with Ep = 0.216V in pH = 7.0, showing that the Cu(PMαFP) 2 en/glassy carbon modified electrode has an electrocatalytic activity toward uric acid.

show abstract

“…Acylpyrazolones are an interesting class of β-diketone compounds which are widely used as solvent extractions of metal ions, laser working materials and NMR shift-reagents [1][2][3]. Their metal complexes have been found to display catalytic performance, biological activity and enhanced luminescence.…”

Section: Introductionmentioning

confidence: 99%

A novel cobalt(II) acylpyrazolonate complex with intermolecular hydrogen bond: Synthesis, structure and properties

Zhang

et al. 2010

Inorganic Chemistry Communications

View full text Add to dashboard Cite

A simple synthesis of novel extraction reagents. 4-Acyl-5-pyrazolone-substituted crown ethers

Cited by 20 publications

References 17 publications

Specific Cooperative Effect of a Macrocyclic Receptor for Metal Ion Transfer into an Ionic Liquid

Specific Cooperative Effect of a Macrocyclic Receptor for Metal Ion Transfer into an Ionic Liquid

Synthesis, crystal structure and electrocatalytic behavior of a copper (II) complex derived from acylpyrazolone double Schiff bases

A novel cobalt(II) acylpyrazolonate complex with intermolecular hydrogen bond: Synthesis, structure and properties

Contact Info

Product

Resources

About