First Row Divalent Transition Metal Complexes of Aryl-Appended Tris((pyridyl)methyl)amine Ligands:  Syntheses, Structures, Electrochemistry, and Hydroxamate Binding Properties

Makowska-Grzyska, M.; Szajna, Ewa; Shipley, Crystal; Arif, Atta M.; Mitchell, Michael H.; Halfen, Jason A.; Berreau, Lisa M.

doi:10.1021/ic034810y

Cited by 58 publications

(93 citation statements)

References 57 publications

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“…[4] Although condensation from simple pyridyl-based precursors of the ligands may be carried out, [5,23] we started directly with the preformed Br2TPA tripod, for convenience, and treated it with 2,3-dimethoxyphenylboronic acid. The tetramethoxy derivative BDMPTPA obtained was then treated with BBr 3 to yield the catechol-containing ligand BCATTPA.…”

Section: Resultsmentioning

confidence: 99%

The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

Machkour

Thallaj

Benhamou

et al. 2006

Chemistry A European J

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Coordination of FeCl3 to the title ligand yields a mononuclear iron(III) complex 1, which was characterized by spectroscopic techniques and X-ray diffraction. The ligand is (kappa3-N) tridentate and the metal, which lies in a pseudo-octahedral environment, is bound to a phenolate group from the catechol substituent. The dichloroiron(II) complex 2 was easily obtained by metalation of the ligand with FeCl2 and characterized by various spectroscopic techniques. In their cyclic voltammograms both 1 and 2 display the same reversible FeII/FeIII wave at E1/2=10 mV (vs. SCE). Reduction of compound 1 with Zn/Hg yields 2', which displays identical properties to 2. Taken together, these findings indicate that in spite of the different oxidation state of the metal in 2, no major geometrical/structural change is observed at the metal center with respect to 1. The reaction of 2 with dioxygen in the absence of organic substrates proceeds extremely rapidly and yields compound 3, which is a diiron(III) derivative whose X-ray crystal structure is also reported. The possibility of a radical-based mechanism is discussed. Compound 3 displays an unusual geometry: one iron(III) center is seven-coordinate, whereas the other lies in a square-pyramidal environment. The two iron atoms are bridged by the catecholato substituents. To the best of our knowledge, 3 is the first example of a seven-coordinate iron(III) derivative with tris(2-pyridylmethyl)amine ligands.

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Section: Resultsmentioning

confidence: 99%

The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

Machkour

Thallaj

Benhamou

et al. 2006

Chemistry A European J

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“…[21] Several aryl-appended pyridinecarboxaldehydes (3,5-(dimethyl)phenyl, 3-(nitro)phenyl, 3-(trifluoromethyl)phenyl, 3-(chloro)phenyl, 3-(methyl)phenyl, 3-(methoxy)phenyl, and 4-methoxy-(phenyl), and 2,3-dihydroxo(phenyl) have been prepared using this procedure starting from the appropriate boronic acid. [22,23] The latter reaction has thus far only been used for the preparation of 6-(4-OMePh)TPA, 6-(3-CNPh)TPA, BCATTPA, and a-MePh 2 TPA ( Figure 1). [24][25][26] A procedure for the preparation of o-d 1 -6-phenyl-2-pyridinecarboxaldehyde has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Coordination and Bioinorganic Chemistry of Aryl-Appended Tris(2-Pyridylmethyl)amine Ligands

Berreau¹

2007

Comments on Inorganic Chemistry

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Aryl-appended tris(2-pyridylmethyl)amine ligands are a relatively new class of chelate ligands in coordination and synthetic bioinorganic chemistry. As outlined herein, to date, coordination complexes of such ligands have been prepared and characterized for first row metal ions from groups 7-12. These studies revealed key coordination properties for this family of ligands. Aryl-appended tris(2-pyridylmethyl)amine ligands have been recently employed in synthetic, biologically relevant metal complexes that exhibit: 1) arene hydroxylation reactivity relevant to non-heme iron-containing containing enzymes that hydroxylate aromatic amino acids; and 2) structural and reactivity properties relevant to Ni(II)-containing acireductone dioxygenase, urease, and glyoxalase I enzymes.

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“…The 6-Ph 2 TPA {N,Nbis[(6-phenyl-2-pyridyl)methyl]-N-(2-pyridylmethyl)amine} ligand was synthesized according to a previously published procedure. [32] Physical Methods:…”

Section: Methodsmentioning

confidence: 99%

A Nickel‐Containing Model System of Acireductone Dioxygenases that Utilizes a C(1)‐H Acireductone Substrate

Allpress

Berreau

2014

Eur J Inorg Chem

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β‐Hydroxy‐α‐amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of β‐hydroxy‐α‐amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one‐flask protocol. Enolization of (R,R)‐ or (S,S)‐pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldehyde or ketone substrate affords aldol addition products that are stereochemically homologous with L‐ or D‐threonine, respectively. These products, which are typically solids, can be obtained in stereoisomerically pure form in yields of 55–98 %, and are readily transformed into β‐hydroxy‐α‐amino acids by mild hydrolysis or into 2‐amino‐1,3‐diols by reduction with sodium borohydride. This new chemistry greatly facilitates the construction of novel antibiotics of several different classes.

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First Row Divalent Transition Metal Complexes of Aryl-Appended Tris((pyridyl)methyl)amine Ligands: Syntheses, Structures, Electrochemistry, and Hydroxamate Binding Properties

Cited by 58 publications

References 57 publications

The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

Coordination and Bioinorganic Chemistry of Aryl-Appended Tris(2-Pyridylmethyl)amine Ligands

A Nickel‐Containing Model System of Acireductone Dioxygenases that Utilizes a C(1)‐H Acireductone Substrate

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First Row Divalent Transition Metal Complexes of Aryl-Appended Tris((pyridyl)methyl)amine Ligands: Syntheses, Structures, Electrochemistry, and Hydroxamate Binding Properties

Cited by 58 publications

References 57 publications

The Coordination Chemistry of FeCl3 and FeCl2 to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

The Coordination Chemistry of FeCl3 and FeCl2 to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

Coordination and Bioinorganic Chemistry of Aryl-Appended Tris(2-Pyridylmethyl)amine Ligands

A Nickel‐Containing Model System of Acireductone Dioxygenases that Utilizes a C(1)‐H Acireductone Substrate

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Product

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The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment

The Coordination Chemistry of FeCl₃ and FeCl₂ to Bis[2‐(2,3‐dihydroxyphenyl)‐6‐pyridylmethyl](2‐pyridylmethyl)amine: Access to a Diiron(III) Compound with an Unusual Pentagonal‐Bipyramidal/Square‐Pyramidal Environment