Electrochemical Parametrization in Sandwich Complexes of the First Row Transition Metals

Lu, Shuangxing; Strelets, V. V.; Ryan, Matthew F.; Pietro, William J.; Lever, A. B. P.

doi:10.1021/ic950620e

Cited by 134 publications

(121 citation statements)

References 124 publications

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“…This trend can be better illustrated by the linear free-energy correlation between the po-tential of the ferrocene/ferrocenium oxidation and Hammett σ p constants of the substituents (Figure 9). Although the absolute difference of the redox potentials is only 70 mV, their good correlation with σ p indicates that the phenylethynyl moiety efficiently conveys the electronic influence of the remote modifying group, which corresponds with the observations made in the series of phenyl- [26,27] and (2-phenylethenyl)-substituted [27,28] ferrocenes. …”

Section: Electrochemistrysupporting

confidence: 80%

Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene

et al. 2008

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Catalysts formed in situ from [Mo(CO) 6 ] and halophenols in dichloromethane efficiently promote cross metathesis reactions of (prop-1-yn-1-yl)ferrocene with various functionalized alkynes to give the corresponding alkynylferrocenes with good selectivity and yields. Optimization of the reaction conditions by changing the phenol component has been carried out, revealing a critical influence of the phenol structure on the reaction yield. The structures of selected compounds were determined by single-crystal X-ray diffraction, and the

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Section: Electrochemistrysupporting

confidence: 80%

Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene

et al. 2008

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“…Obviously, the electron-donating effect of the amino groups to the metal centre is additive. [34] In the solid-state IR absorption spectrum of 6 the characteristic amide vibrations confirm the presence of hydrogen bonds (Table 5). In dilute solutions, however, the bands assigned to amide A and amide I are shifted to higher energies, while that of amide II is shifted to a lower energy, suggesting that hydrogen bonding is absent (Table 5).…”

mentioning

confidence: 93%

Main Chain Ferrocenyl Amides from 1‐Aminoferrocene‐1′‐carboxylic Acid

2004

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The non‐natural amino acid 1‐aminoferrocene‐1′‐carboxylic acid is synthesised from ferrocene in eight steps. The folding and association phenomena of amido‐substituted ferrocenes in the crystal as well as in solution are studied by X‐ray crystallography, IR and NMR spectroscopy and DFT calculations. The amino acid is selectively protected at the amino group with the use of the fluorenyl‐9‐methoxycarbonyl (Fmoc) group. An amide‐linked ferrocene dimer is prepared using the HOBt/DCC protocol for amide formation. In the crystal the dimer forms a hydrogen‐bonded sheet structure, while in solution dynamic intramolecular hydrogen bonds are observed by VT 1H NMR and IR spectroscopy. The dynamic flipping process has been rationalised by DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…[43] The potential differences of 320 (Fmoc-3), [43] 290 (Boc-3) and 295 mV (Ac-3) [14] are largely due to substituent effects [49] and to some degree (ca. 125 mV) due to electronic interaction between the redox sites.…”

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confidence: 99%

Oligonuclear Ferrocene Amides: Mixed‐Valent Peptides and Potential Redox‐Switchable Foldamers

Siebler

Linseis

Gasi

et al. 2011

Chemistry A European J

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Trinuclear ferrocene tris-amides were synthesized from an Fmoc- or Boc-protected ferrocene amino acid, and hydrogen-bonded zigzag conformations were determined by NMR spectroscopy, molecular modelling, and X-ray diffraction. In these ordered secondary structures orientation of the individual amide dipole moments approximately in the same direction results in a macrodipole moment similar to that of α-helices composed of α-amino acids. Unlike ordinary α-amino acids, the building blocks in these ferrocene amides with defined secondary structure can be sequentially oxidized to mono-, di-, and trications. Singly and doubly charged mixed-valent cations were probed experimentally by Vis/NIR, paramagnetic ¹H NMR and Mössbauer spectroscopy and investigated theoretically by DFT calculations. According to the appearance of intervalence charge transfer (IVCT) bands in solution, the ferrocene/ferrocenium amides are described as Robin-Day class II mixed-valent systems. Mössbauer spectroscopy indicates trapped valences in the solid state. The secondary structure of trinuclear ferrocene tris-amides remains intact (coiled form) upon oxidation to mono- and dications according to DFT calculations, while oxidation to the trication should break the intramolecular hydrogen bonding and unfold the ferrocene peptide (uncoiled form).

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Electrochemical Parametrization in Sandwich Complexes of the First Row Transition Metals

Cited by 134 publications

References 124 publications

Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene

Mo‐Catalyzed Cross‐Metathesis Reaction of Propynylferrocene

Main Chain Ferrocenyl Amides from 1‐Aminoferrocene‐1′‐carboxylic Acid

Oligonuclear Ferrocene Amides: Mixed‐Valent Peptides and Potential Redox‐Switchable Foldamers

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