Elucidating the Mode of Action of a Corrosion Inhibitor for Iron

Frey, Marcus; Harris, Steven G.; Holmes, Jeremy M.; Nation, David A.; Parsons, Simon; Tasker, Peter A.; Winpenny, Richard E. P.

doi:10.1002/(sici)1521-3765(20000417)6:8<1407::aid-chem1407>3.3.co;2-b

Cited by 16 publications

(25 citation statements)

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“…All Fe cations lie in one plane [maximum deviation of the least-squares plane through the ten Fe ions is 0.030 (1) A Ê ]. Similar structures have been reported with other carboxylate anions: chloroacetate (Taft et al, 1994), acetate (Benelli et al, 1996) and 3-(4-methylbenzoyl)propionate (Frey et al, 2000). In all these structures, the triple link between pairs of adjacent iron cations is formed by one carboxylate anion and two methoxo anions.…”

Section: Commentsupporting

confidence: 80%

cyclo-Decakis(μ-2,2-diphenylacetato-O,O′)dodecakis(μ-methoxo)decairon(III)) mixed solvate

et al. 2002

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The title compound, [Fe10(C14H11O2)10(CH3O)20], takes the form of a so‐called `ferric wheel', consisting of ten Fe cations, linked by carboxylate and methoxo anions. The complex is ring‐shaped with the moiety formula [FeIII(carboxylate)(methoxo)2]10 and is located on a crystallographic inversion centre. The unit cell contains two independent regions filled with disordered solvent of unknown composition.

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Section: Commentsupporting

confidence: 80%

cyclo-Decakis(μ-2,2-diphenylacetato-O,O′)dodecakis(μ-methoxo)decairon(III)) mixed solvate

et al. 2002

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“…Restricting further discussion to the so‐called ferric wheels with nuclearities equal to or higher than ten, the structurally characterized complexes that contain O‐donor groups as bridging ligands are [{Fe(OMe) 2 (O 2 CCH 2 Cl)} 10 ]14a [{Fe(OMe) 2 (O 2 CMe)} 10 ]14b [{Fe(OMe) 2 L} 10 ]14c where L − is the monoanion of 3‐(4‐methylbenzoyl)propionic acid, [{Fe(OMe) 2 (dbm)} 12 ],14d where dbm − is the dibenzoylmethanato ligand, and [{Fe(OH)(XDK)Fe 2 (OMe) 4 (O 2 CMe) 2 } 6 ],14e where XDK 2− is the ion of m ‐xylylenediamine bis(Kemp's triacid imide). All three Fe$\rm{^{III}_{10}}$ wheels contain chemically equivalent ( μ ‐O 2 CR)( μ ‐OMe) 2 units, while the Fe$\rm{^{III}_{12}}$ wheel contains chemically equivalent ( μ ‐OMe) 2 units.…”

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confidence: 99%

“…The family of ferric wheels with the ( μ ‐O 2 CR)( μ ‐OR′) 2 unit is restricted to decanuclear complexes 14a–14c. We wondered whether change of the carboxylato or/and alkoxo ligands would influence the size of these wheels and permit the isolation of larger wheels.…”

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confidence: 99%

[{Fe(OMe)2[O2CC(OH)Ph2]}12]: Synthesis and Characterization of a New Member in the Family of Molecular Ferric Wheels with the Carboxylatobis(alkoxo) Bridging Unit

Raptopoulou

Tangoulis

Devlin

2002

Angew. Chem. Int. Ed.

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High-nuclearity transition-metal clusters continue to attract a great deal of interest, partly because of their fascinating physical properties and partly for the architectural beauty of their structures. An interesting subarea of 3d metal cluster chemistry is the small but growing family of molecules that have circular structures. Large cyclic polymetallic clusters are valued for their ability to mimic the properties of linear coordination polymers. [1] For example, theories developed for analyzing magnetically coupled ring systems have been extensively applied to calculate the thermodynamic properties of 1D materials. [2] Furthermore, the chemistry of circular molecular clusters is also associated with supramolecular chemistry. Anion and cation recognition provide the possibility of controlling the size of clusters. A representative example of this approach is the ability to address the synthesis of molecular rings by exploiting host ± guest interactions with alkali-metal cations, because alkali-metal cations are hosted by rings of different size. Thus, hexairon(iii) [3±5] and hexamanganese(iii) [6] complexes with cyclic M 6 O 12 cores can easily accommodate Li and Na ions, both in the solid state and in solution, whereas Cs ions require larger rings, such as M 8 O 16 . [5] Metal rings have excited mankind since mythological times. [7] The largest cyclic structure containing exclusively paramagnetic 3d metals is the Ni II 24 wheel reported by Winpenny and co-workers, [8] which is approximately an order of magnitude smaller that the giant wheels constructed from molybdate fragments by the M¸ller group; [9] a Ni II 12 wheel is also known. [10] Large, cyclic, polymetallic arrangements of other 3d metals, either unsupported or supported (by ions or molecules as guests), have been found for chromium(iii), [11] manganese(iii), [12] iron(ii), [13] iron(iii), [12, 14] cobalt(ii), [15] and copper(ii). [16] Restricting further discussion to the so-called ferric wheels with nuclearities equal to or higher than ten, the structurally characterized complexes that contain O-donor groups as bridging ligands are [{Fe(OMe) 2

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“…Similar 4-keto acids based on 3-benzoylpropionic acid, which does not contain the phenolic hydroxyl group, have been characterized crystallographically. These include two polymorphs of 3-benzoylpropionic acid (Selladurai et al, 1990;Thompson et al, 1991), 4-(4-biphenyl)-4-oxobutyric acid (Kim et al, 1988), 3-[4-(methylsulfonyl)benzoyl]propionic acid (Lynch & McClenaghan, 2002) and 3-(4-methylbenzoyl)propionic acid (Ircagor 419; Frey et al, 2000), which is used as a corrosion inhibitor for mild steel. All structures contain the dimeric carboxylic acid hydrogen bonding seen in the title compound.…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound was synthesized as a potential corrosion inhibitor as it has a structure similar to that of successful reagent Ircagor 419 TM (Frey et al, 2000) and, in addition, includes a phenolic hydroxyl group which may coordinate to a metal or form hydrogen bonds to the surface. The molecules in the crystal structure form dimers via H-bonding between two adjacent carboxylate moieties (O4-H4•••O3 = 2.642 (1) Å; Figure 1) which is typical for carboxylate structures.…”

Section: S1 Commentmentioning

confidence: 99%

3-(5-tert-Butyl-2-hydroxybenzoyl)propanoic acid

et al. 2007

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Key indicators: single-crystal X-ray study; T = 150 K; mean (C-C) = 0.002 Å; R factor = 0.052; wR factor = 0.142; data-to-parameter ratio = 23.4.The title compound, C 12 H 18 O 4 , was synthesized as a part of an investigation into corrosion inhibitors, as it is structurally related to the commercial reagent Ircagor 419. The molecules form centrosymmetric dimers due to hydrogen bonding involving the carboxyl groups, typical for the crystal structures of carboxylic acids. There is also an intramolecular hydrogen bond between the phenol hydroxyl group and the ortho keto O atom.interactions between benzene rings link the molecules into stacks running along the a axis (distances between the planes of adjacent molecules are 3.305 and 3.389 Å ). Intermolecular hydrogen bonds, together with the stacking interactions, give rise to infinite sheets parallel to the ac plane of the crystal structure.

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Elucidating the Mode of Action of a Corrosion Inhibitor for Iron

Cited by 16 publications

References 0 publications

cyclo-Decakis(μ-2,2-diphenylacetato-O,O′)dodecakis(μ-methoxo)decairon(III)) mixed solvate

cyclo-Decakis(μ-2,2-diphenylacetato-O,O′)dodecakis(μ-methoxo)decairon(III)) mixed solvate

[{Fe(OMe)2[O2CC(OH)Ph2]}12]: Synthesis and Characterization of a New Member in the Family of Molecular Ferric Wheels with the Carboxylatobis(alkoxo) Bridging Unit

3-(5-tert-Butyl-2-hydroxybenzoyl)propanoic acid

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