Functional micellar catalysis. Part 8. Catalysis of the hydrolysis of p-nitrophenyl picolinate by metal-chelating micelles containing copper(II) or zinc(II)

Fornasier, Roberto; MILANI, D.; Scrimin, Paolo; Tonellato, Umberto

doi:10.1039/p29860000233

Cited by 47 publications

(45 citation statements)

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“…Starting from diethyl ester of dipicolinic acid (2), reduction with substoichiometric amounts of NaBH 4 affords the 6-hydroxymethyl-ethyl picolinic ester in 49 % yield, [19,20] which was transformed into the chlorinated compound 3 in 96 % yield by treatment with SOCl 2 . [21] Amine 4 was obtained by a Gabriel synthesis by treating 3 with sodium phthalimidate in DMF at room temperature (92 %) followed by treatment with hydrazine in refluxing ethanol (quantitative). [21] Nucleophilic substitution of 4 with 1 afforded the intermediate 5 in 67 % yield, from which a carboalkoxylation reaction [17] gave the ester precursor 6 in 45 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…[21] Amine 4 was obtained by a Gabriel synthesis by treating 3 with sodium phthalimidate in DMF at room temperature (92 %) followed by treatment with hydrazine in refluxing ethanol (quantitative). [21] Nucleophilic substitution of 4 with 1 afforded the intermediate 5 in 67 % yield, from which a carboalkoxylation reaction [17] gave the ester precursor 6 in 45 % yield. Saponification of 6 with NaOH followed by neutralisation with hydrochloric acid gave ligand L 1 H 3 in 42 % yield as its tetrahydrochloride salt.…”

Section: Resultsmentioning

confidence: 99%

“…[35] IR spectra were recorded by using a Nicolet 210 spectrometer as KBr pellets. Compounds 1, [16] 3, [20] 4 [21] and 7 [22] were obtained according to literature procedures and full experimental procedures for the synthesis of intermediate compounds 5, 6, 8, 9, 10, 13, 14, 16, 17, and 20 are reported in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

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Relationship Between the Ligand Structure and the Luminescent Properties of Water‐Soluble Lanthanide Complexes Containing Bis(bipyridine) Anionic Arms

Charbonnière

Weibel

Retailleau

et al. 2006

Chemistry A European J

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A series of six new ligands (L1–L6) suitable for the formation of luminescent lanthanide complexes in water is described. Ligands L1–L4 are constructed from two 6′‐carboxy‐6‐methylene‐2,2′‐bipyridine chromophoric arms bonded to the amino function of a 2‐aminomethylene‐6‐carboxy‐pyridine (L1), an N,N‐diacetate‐ethylene diamine (L2), a serine (L3), or an aminomalonic acid (L4). For ligands L5 and L6, the linking amino function is provided by a glutamic acid, and the anionic functions at the 6′‐position of the bipyridyl arms are made of the sodium salts of monoethylphosphonic ester (L5) and phosphonic acid (L6). The synthesis and characterisation of the ligands are described, together with the study of the formation of lanthanide complexes with europium and terbium. In the case of L3, the europium complex obtained in acidic conditions was crystallised and the X‐ray crystal structure is depicted. Photophysical properties of the complexes were studied by means of UV‐visible absorption, and steady‐state and time‐resolved luminescence spectroscopy. Excited‐state luminescence lifetimes of the complexes were determined in water and deuterated water to gain insight into the number of water molecules directly coordinated in the first coordination sphere of the complexes. The coordination behaviour of the series of ligands is questioned in the light of the spectroscopic data and discussed in terms of protection of the cation towards water molecules and their impact on the luminescence efficiency.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Relationship Between the Ligand Structure and the Luminescent Properties of Water‐Soluble Lanthanide Complexes Containing Bis(bipyridine) Anionic Arms

Charbonnière

Weibel

Retailleau

et al. 2006

Chemistry A European J

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“…1,2 Among these, surfactants with counterions acting as active catalysts form a special class. [3][4][5][6][7][8][9] Metallo-micelles have been reported as catalysts for several types of reactions. [3][4][5]8,9 Other examples include catalysis of DNA hydrolysis by cerium phosphate bilayers 10 and catalysis of aldol reactions by lanthanide dodecyl sulfate dispersions.…”

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confidence: 99%

“…[3][4][5][6][7][8][9] Metallo-micelles have been reported as catalysts for several types of reactions. [3][4][5]8,9 Other examples include catalysis of DNA hydrolysis by cerium phosphate bilayers 10 and catalysis of aldol reactions by lanthanide dodecyl sulfate dispersions. 6,11 Herein, we report efficient catalysis of a Diels-Alder reaction by vesicles, composed of a phosphate surfactant, with copper(II) as the active counterion.…”

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confidence: 99%