Extraction, complex formation and spectrophotometric determination of iron(III) with 2-carbethoxy-5-hydroxy-1-(4-tolyl)-4-pyridone

Herak, Mirta; Janko, M.; Tamhina, B.

doi:10.1007/bf01218137

Cited by 8 publications

(3 citation statements)

References 14 publications

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“…The six-membered pyridinone ring systems in both Hpap and Hcmp are slightly, but significantly, nonplanar (maximum deviations from the meaaplanes being 0.0203 (19) A in the former and 0.0099 (13) A in the latter), as noted earlier for 3-hydroxy-2-methyl-4-pyridinone (Hmpp) and 3-hydroxy-l,2-dimethyl-4-pyridinone (Hdpp) (8). The deviation from planarity is towards a N(1), C(4) boat in both molecules.…”

Section: Resultsmentioning

confidence: 99%

Physical and structural studies of N-carboxymethyl- and N-(p-methoxyphenyl)-3-hydroxy-2-methyl-4-pyridinone

Zhang¹,

Rettig²,

Orvig³

1992

Can. J. Chem.

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This paper is dedicated to the memory of Professor Thotnas BirchallZAIHUI ZHANG, STEVEN J. RETTIG, and CHRIS ORVIG. Can. J. Chem. 70, 763 (1992). 3-Hydroxy-I-carboxymethyl-2-methyl-4-pyridinone (Hcmp) and 3-hydroxy-I-(p-rnethoxypheny1)-2-methyl-4-pyridine (Hpap) have been prepared and studie! by single crystal X-ray diffraction. Crystals of Hcmp are monoclinic, a = 6.340 (2), b = 7.705 (I), c = 16.226 (1) A, P = 94.74 (I), Z = 4, space group P 2 , / n and those for Hpap are monoclinic, a = 10.8435 (9), b = 16.680 (2), c = 13.5665 (6) A, P = 109.450 (4), Z = 8, space group C 2 / c . Both structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.030 and 0.041 (R,, = 0.039 and 0.058) for 1642 and 1819 reflections with I 2 3u(I), respectively. Bond lengths and bond angles in the two compounds are normal; however, Hcmp forms as a zwitterion in the solld state. The two compounds were also studied by mass spectrometry, UV, infrared, proton NMR spectroscopies, and potentiometric equllibnum measurements. The protonation constants for Hcrnp are log Kl = 9.76 (I), log K2 = 3.43 (I), and log K, = 2.78 (3) and for Hpap are log K ; = 9.42 (4) and log K ; = 3.16 (8).Key words: 3-hydroxy-4-pyridinone, zwitterion, hydrogen bonding, protonation constant, crystallography, solid state. Introduction N-aryl (2) substituted-3-hydroxy-2-methyl-4-pyridinones and AS part of our project to examine the coordination themtheir metal complexes have been reported (7,8). he studistry and biochemical properties of aluminum, gallium, and ies have shown that these complexes have unique Properindium complexes, we have been studying tris(ligand) cornties: reasonable water solubility, variable lipophilicity, high plexes of these metal ions with 3-hydroxy-4-pyrones (1 -3) thermodynamic stability, and interesting biological activity and 3-hydroxy-4-pyridinones (4-7) as bidentate ligands. The (7, 9-1 1). preparation and characterization of a series of N-alkyl (1) and

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Section: Resultsmentioning

confidence: 99%

Physical and structural studies of N-carboxymethyl- and N-(p-methoxyphenyl)-3-hydroxy-2-methyl-4-pyridinone

Zhang¹,

Rettig²,

Orvig³

1992

Can. J. Chem.

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“…The excellent chelating properties exhibited by the 3-hydroxy-4-pyridinone ligands towards M(III) and M(II) metal ions, in conjunction with the possibility of synthesizing strongly lipophilic derivatives, also makes this class of ligands useful in the fields of analytical and environmental chemistry. 1-Phenyl-and 1-(4 -tolyl)-3-hydroxy-4-pyridinones have been assessed as reagents for the spectrophotometric determination of, inter alios, Fe(III), 26,27 Ti(IV), 28 V(V) 29 and Nb(V). 30 Some 1-aryl-3-hydroxy-4-pyridinone derivatives have been demonstrated to be effective as extractants, from aqueous media, for a variety of metals such as Ga(III), 31 Fe(III), 32 Hf(IV), 33 Zr(IV), 34 Nb(V), 35 Ta(V) 36, 37 and U(VI).…”

Section: Introductionmentioning

confidence: 99%

New lipophilic 3-hydroxy-4-pyridinonate iron(iii) complexes: synthesis and EXAFS structural characterisation

et al. 2006

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New tris-iron(III) chelates of 3-hydroxy-4-pyridinone ligands derived from maltol (3-hydroxy-2-methyl-4-pyrone) or ethylmaltol (2-ethyl-3-hydroxy-4-pyrone), including a variety of N-aryl (phenyl, 4'-tolyl, 4'-(n-butyl)phenyl, 4'-(n-hexyl)phenyl) and N-benzyl (4'-methylbenzyl, 4'-fluorobenzyl and 4'-(trifluoromethyl)benzylamine) substituents on the nitrogen atom of the pyridinone ring, have been prepared. Characterization by C,H,N elemental analysis and thermogravimetric measurements indicates that most of the complexes are obtained as hydrates of general formula ML3.xH2O. Structural characterization of these difficult to crystallize lipophilic complexes has been achieved by EXAFS spectroscopy. Solutions of iron(III) complexes of maltol, ethylmaltol, 1,2-dimethyl-3-hydroxy-4-pyridinone and 1-phenyl-2-methyl-3-hydroxy-4-pyridinone in methanol-water mixtures were also examined by EXAFS. Distances from the central atom to ligand atoms, within 6 A of the metal, have been determined in the solid and solution samples and the results show that the structure observed in the powder is maintained in solution. The local structure around the metal centre, bond distances and bond angles, does not change significantly with variable lipophilicity, thus indicating that ligands may be tailored according to specific needs without altering their chelation properties. EXAFS data analysis for this set of tris-iron(III) compounds illustrates the important contribution of both intra-ligand and inter-ligand multiple scattering pathways through the metal centre to a peak observed in the FT spectrum at twice the metal ligand distance (approximately 4 A). The present results demonstrate that EXAFS features at twice the metal-ligand distance are valuable in the assignment of molecular geometry and that location of hydration water molecules, by EXAFS analysis, is limited by the geometry of the complexes, in particular for those in which ligands containing phenyl rings are present.

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“…They can react sensitively with a lot of ligands or chromogenic agents such as 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol [1] , ophenanthroline, 2 2,3-dihydroxynaphtalene 3 and so on. [4][5][6][7][8][9][10][11][12] The synthesis of a phenylfluorone derivant, o-chlorophenylfluorone (o-CPF) was reported 13 with the following structure:…”

Section: Introductionmentioning

confidence: 99%

Spectrophotometric Investigation of Cu and Fe Complexes with o-Chlorophenylfluorone and Selective Competition Coordination Determination of Iron Traces

2002

Bulletin of the Korean Chemical Society

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The two reactions between iron ion (Fe 3+) and o-chlorophenylfluorone (o-CPF) and copper ion (Cu 2+) and o-CPF are sensitive at pH 6 in the presence of Triton X-100. We have determined the formation constants of the complexes by the spectral correction technique. Because of the poor selectivity of o-CPF to metals, the competition coordination of only the iron ion from the Cu-o-CPF complex was found and applied to the selective detection of iron traces by the Selective Competition Coordination Determination (SCCD) approach. The analysis of several samples shows that the relative standard deviations are less than 5.0% and the recovery of iron ions between 94.5% and 106%.

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Extraction, complex formation and spectrophotometric determination of iron(III) with 2-carbethoxy-5-hydroxy-1-(4-tolyl)-4-pyridone

Cited by 8 publications

References 14 publications

Physical and structural studies of N-carboxymethyl- and N-(p-methoxyphenyl)-3-hydroxy-2-methyl-4-pyridinone

Physical and structural studies of N-carboxymethyl- and N-(p-methoxyphenyl)-3-hydroxy-2-methyl-4-pyridinone

New lipophilic 3-hydroxy-4-pyridinonate iron(iii) complexes: synthesis and EXAFS structural characterisation

Spectrophotometric Investigation of Cu and Fe Complexes with o-Chlorophenylfluorone and Selective Competition Coordination Determination of Iron Traces

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