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IR and Raman spectra of Some Ferrocene Derivatives. Torsional Barriers and Thermodynamyc Functions

The Ir and Raman spectra of gaseous (C5H5)Fe(C5H4COCH3) and (C5H4COCH3)2Fe were recorded in the frequency range 20-4000 cm-1.Both the gaseous complexes show a Raman absorption at 41 +/- 2 cm-1 which was assigned to the torsional frequency omega0.1 .In these molecules a barrier of 1000 +/- 100 cal/mol restricts the rotation of the cyclopentadienyl ring with respect to the rigid frame.The thermodynamic functions of the gaseous ferrocenes are reported in the temperature range 298-450 deg K.

IR and Raman spectra of Some Ferrocene Derivatives. Torsional Barriers and Thermodynamyc Functions

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Development of a convenient new synthetic route to [3]ferrocenophanones

[3]Ferrocenophanone rac-8 was prepared by several non-Friedel-Crafts pathways starting from a Mannich-type coupling of 1,1?-diacetylferrocene followed by catalytic hydrogenation. Hydride abstraction from the resulting alpha-dimethylamino[3]ferrocenophane rac-14 with B(C6F 5)3 followed by hydrolysis gave the ketone rac-8. Several variants of the Sommelet reaction, using ethylglyoxylate, formaldehyde or hexamethylenetetramine (urotropine) as the “oxidizing” reagent gave the alpha-[3]ferrocenophanone 8 in good to excellent yield. Some variants of these reactions were also used for the preparation of the pure enantiomer (R)-8. The electrochemical behaviour of 8 has been investigated and compared with related derivatives. The Royal Society of Chemistry 2006.

Development of a convenient new synthetic route to [3]ferrocenophanones

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Nucleophilic aromatic substitution of 2-(3(5)-pyrazolyl)pyridine: A novel access to multidentate chelate ligands

1-(Nitrophenyl) functionalized 2-(3-pyrazolyl)pyridines were obtained by a nucleophilic aromatic substitution and could be reduced to the corresponding aminophenyl substituted derivatives. These compounds can be used to co-ordinate transition metal sites or for the generation of building blocks for supramolecular chemistry. The solid state structure of a 1,1?- functionalized ferrocene, which was obtained following this route, is discussed in detail.

Nucleophilic aromatic substitution of 2-(3(5)-pyrazolyl)pyridine: A novel access to multidentate chelate ligands

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Functionalized 1,1-Ethenedithiolates as Ligands, III. Palladium(II) and Platinum(II) Complexes with Ferrocenyl-Substituted 1,1-Ethenedithiolate Ligands. Crystal Structure Analyses of cis-(Ph3P)2M (M = Pd, Pt)

The ferrocenyl-substituted mono- (3) and 1,1′-bis-dithiocarboxylic acids (4) have been prepared.These acids react with L2MCl2 (M = Pd, Pt; L = PEt3, PPh3, and 1/2 dppe) in the presence of sodium acetate to give the cis heterodi- and heterotrimetallic complexes cis-L2M (5a: M = Pd, L = PPh3; 5b: M = Pt, L = PPh3; 5c: M = Pt, L = 1/2 dppe) and 2Fe (6a: M = Pd, L = PPh3; 6b: M = Pt, L = PEt3; 6c: M = Pt, L = PPh3; 6d: M = Pt, L = 1/2 dppe).The structures of 5a and 5b have been determined by single-crystal X-ray diffraction. – Key Words: Ferrocene derivatives / 1,1-Ethenedithiolate complexes / Group 10 metal complexes / Heterodimetallic compounds / Heterotrimetallic compounds

Functionalized 1,1-Ethenedithiolates as Ligands, III. Palladium(II) and Platinum(II) Complexes with Ferrocenyl-Substituted 1,1-Ethenedithiolate Ligands. Crystal Structure Analyses of cis-(Ph3P)2M (M = Pd, Pt)

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Experimental charge density analysis of symmetrically substituted ferrocene derivatives

Experimental charge density analysis of three symmetrically substituted ferrocene derivatives: 1,?- dimethyl ferrocene (1), decamethyl ferrocene (2), and 1,?-diacetyl ferrocene (3) was conducted. The electron donating or accepting propensities of the ferrocene substituents were evaluated. The metal ligand interactions in all analyzed compounds were found to be similar in terms of charge density concentrations at Bond Critical Points (BCPs), laplacian values, and deformation density features. The monopole population of iron in all cases tend to be slightly negative, suggesting charge donation from Cp ligands. d orbital populations in all cases adopt values in agreement with theoretical calculations and ligand field theory. The charge distribution over analyzed molecules does not correlate with the formal oxidation potential in the analyzed compounds, as compound 2 in the currently studied structure takes the place suitable for an unsubstituted ferrocene. The non-intuitive low energy of the eclipsed conformation of 1 compound finds some explanation in the existence of a bond critical point between atoms of the two methyl groups in the structure. An asymmetry of the atomic surroundings of the two oxygen atoms in the 3 structure, reflected by the differences in charge rho(rBCP) and ?2rho(rBCP) values and the shape of deformation density in the regions of oxygen lone electron pairs, is described.

Experimental charge density analysis of symmetrically substituted ferrocene derivatives

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Inclusion complexes of ferrocenes and beta-cyclodextrins. Critical appraisal of the electrochemical evaluation of formation constants

We report the results of a systematic electrochemical study of the host-guest supramolecular adducts between ferrocene (Fc), ferrocenium cation (Fc+), and other mono- and disubstituted ferrocene derivatives with different beta-cyclodextrins (CD) in mixed organic-aqueous media. The influence on the formation constants (Kf) of the organic cosolvent, the different substituents on Fc, and the type of CDs are evaluated. NMR and conductometry responses of ferrocenium cation solutions in the presence of CD confirm the weak propensity of Fc+ to enter into the cyclodextrin cavity. The Kf value generally decreases as the steric bulk and the rigidity of Fc substituents increases, consistent with an inclusion model in which the Fc fits into the CD cavity in an axial mode while the substituent protrudes out. Interestingly, the addition of sulfated beta-CD shifts the redox Fc/Fc+ couple toward cathodic values, indicating that the oxidized, cationic form Fc+ is more strongly bound to the sulfated cyclodextrin than neutral Fc, probably by means of electrostatic interaction with the external -SO3- functionalities.

Inclusion complexes of ferrocenes and beta-cyclodextrins. Critical appraisal of the electrochemical evaluation of formation constants

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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From diacetylferrocene to 1,1?-ferrocenyldiimines: Substituent effects on synthesis, molecular structure, electrochemical behavior and optical absorption property

A series of 1,1?-ferrocenyldiimines [Fe{(eta5-C5H4)-C(Me)N-R}2 ], where R = n-hexyl 1a, cyclohexyl 1b, phenyl 1c, 4-methoxyphenyl 1d, 3-methoxyphenyl 1e, 4-nitrophenyl 1f, and 3-nitrophenyl 1g, have been synthesized by reactions of ca. 1:2 M ratio of 1,1?-diacetylferrocene and the corresponding amines. While ca. 1:1 M ratio of the starting materials was employed, acetylferrocenylimines [Fe{(eta5-C5H4)-C(CH3){dou ble bond, long}O}{(eta5-C5H4)-C(CH3) {double bond, long}N-R}], where R = 4-nitrophenyl 2f, and 3-nitrophenyl 2g, were obtained. Single crystal X-ray structural analysis revealed that the two cyclopentadienyl rings in 1d, 1e, 1g, 2f, and 2g were antiperiplanar staggered, anticlinal eclipsed, anticlinal eclipsed/synclinal eclipsed, synclinal eclipsed, and synclinal eclipsed to each other in solid state, respectively. All synthesized ferrocene derivatives exhibited a reversible one-electron redox process in their cyclic voltammograms, and the values of their redox potentials relied on the R groups. The correlation between the redox potential and the Hammett substituent constant, sigmap was quite well, with a correlation coefficient of 0.98. The UV-vis spectra showed that their optical property was also substituent dependent.

From diacetylferrocene to 1,1?-ferrocenyldiimines: Substituent effects on synthesis, molecular structure, electrochemical behavior and optical absorption property

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Quality Control of 1,1′-Diacetylferrocene, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1273-94-5, in my other articles.

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The synthesis and structural characterization of N-(ferrocenyl)2 and N-(ferrocenoyl)2 cystine dimethyl ester derivatives: Potential anion sensing agents

Standard peptide coupling reactions were use to prepare the N-(ferrocenyl)2 and N-(ferrocenoyl)2 cystine dimethyl ester derivatives 4-11. The ferrocene carboxylic acids 1 and 3 were treated with 1-hydroxybenzotriazole (HOBt), N-(3-dimethylaminopropyl)-N?- ethylcarbodiimide hydrochloride (EDC), l-cystine methyl ester hydrochloride and triethylamine in dichloromethane at 0 C to furnish compounds 4-9. The preparation of compounds 10 and 11 employed the dipeptide derivatives (glycine)2-l-cystine dimethyl ester and (beta-alanine) 2-l-cystine dimethyl ester respectively. The N-(ferrocenyl) 2 and N-(ferrocenoyl)2 cystine dimethyl ester derivatives 4-11, which are potential anion sensing agents, were spectroscopically characterized by a combination of 1H NMR, 13C NMR, IR, UV, DEPT-135 and 1H-13C COSY (HMQC) spectroscopy, mass spectrometry and cyclic voltammetry. The electrochemical detection of dihydrogen phosphate and adenosine nucleotide anions in aqueous electrolyte by monolayers of {N-(ferrocenoyl)-beta-alanine}2-l-cystine dimethyl ester 11 immobilized on gold electrodes using cyclic voltammetry is described. Immobilization of this receptor on a gold electrode surface enabled the recognition process to be detected in aqueous media. The recognition process is as a result of electrostatic interactions between the ferricenium cation and the anion, and hydrogen bonding interactions between the peptide amide bonds and the anion. The complexation process was amperometrically sensed via a reduction in the peak current of the ferrocene/ferricenium redox couple. A linear relationship (R2 = c. 0.99) was observed between anion concentration and change in peak current in both cases.

The synthesis and structural characterization of N-(ferrocenyl)2 and N-(ferrocenoyl)2 cystine dimethyl ester derivatives: Potential anion sensing agents

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Ferric Heme-Nitrosyl Complexes: Kinetically Robust or Unstable Intermediates?

We have determined a convenient method for the bulk synthesis of high-purity ferric heme-nitrosyl complexes ({FeNO}6 in the Enemark-Feltham notation); this method is based on the chemical or electrochemical oxidation of corresponding {FeNO}7 precursors. We used this method to obtain the five- and six-coordinate complexes [Fe(TPP)(NO)]+ (TPP2- = tetraphenylporphyrin dianion) and [Fe(TPP)(NO)(MI)]+ (MI = 1-methylimidazole) and demonstrate that these complexes are stable in solution in the absence of excess NO gas. This is in stark contrast to the often-cited instability of such {FeNO}6 model complexes in the literature, which is likely due to the common presence of halide impurities (although other impurities could certainly also play a role). This is avoided in our approach for the synthesis of {FeNO}6 complexes via oxidation of pure {FeNO}7 precursors. On the basis of these results, {FeNO}6 complexes in proteins do not show an increased stability toward NO loss compared to model complexes. We also prepared the halide-coordinated complexes [Fe(TPP)(NO)(X)] (X = Cl-, Br-), which correspond to the elusive, key reactive intermediate in the so-called autoreduction reaction, which is frequently used to prepare {FeNO}7 complexes from ferric precursors. All of the complexes were characterized using X-ray crystallography, UV-vis, IR, and nuclear resonance vibrational spectroscopy (NRVS). On the basis of the vibrational data, further insight into the electronic structure of these {FeNO}6 complexes, in particular with respect to the role of the axial ligand trans to NO, is obtained.

Ferric Heme-Nitrosyl Complexes: Kinetically Robust or Unstable Intermediates?

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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1,9-Dicarbonyl-2,8-dioxo-butyne-ester Ferrocenophane: Synthesis, Structure and Recognition Properties for Co2+ and Cu2+ Ions

An efficient highly diluted synthetic approach to the synthesis of 1,9-dicarbonyl-2,8-dioxo-butyne ester ferrocenophane (L) has been developed. The title compound was characterized by IR, UV, FL, 1H NMR, spectroscopies, elemental analysis and so on. Further complex L shows fluorescence responses to Co2+ and Cu2+ in CH3OH, The results indicate that the complex could be applied in multianayte detection. The binding ability of receptor L CH3OH was tested for various cations (Co2+, Cu2+, Zn2+, and Ni2+ in water) and the binding constants for Co2+ and Cu2+ were the computed, having a distinct absorbance shift. The receptor is a very attractive array because its distinct absorbance shift profile in a semi-aqueous phase, making it applicable in the area of biology, environmental sciences and material chemistry.

1,9-Dicarbonyl-2,8-dioxo-butyne-ester Ferrocenophane: Synthesis, Structure and Recognition Properties for Co2+ and Cu2+ Ions

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Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion