Reactions of Cyclopentadienyl (methyl) iron Dicarbonyl with Various Ligands. Cyclopentadienyl(acetyl)iron Carbonyl Phosphine and Phosphite Complexes

Bibler, J.P.; Wojcicki, Andrew

doi:10.1021/ic50039a037

Cited by 123 publications

(35 citation statements)

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“…The lability of metal‐CO coordination bonds allows metal elements to associate within the organic matrix without calcination . PFpPs are also potentially useful as electrets due to the presence of polarized acyl CO groups in each repeat unit.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Main‐Chain Metal Carbonyl Organometallic Macromolecules (MCMCOMs)

Cao

Murshid

Wang

2015

Macromol. Rapid Commun.

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Synthesis of main-chain metal carbonyl organometallic macromolecules (MCMCOMs) is difficult, mainly due to the instability of metal carbonyl complexes. Despite its challenge a number of MCMCOMs has been prepared by strategically using organometallic, organic, and polymer synthetic chemistry. Main contributions to this research field were reported by the groups of Tyler, Pannell, and Wang and are briefly summarized in this article.

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Section: Discussionmentioning

confidence: 99%

Synthesis of Main‐Chain Metal Carbonyl Organometallic Macromolecules (MCMCOMs)

Cao

Murshid

Wang

2015

Macromol. Rapid Commun.

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“…In the molecular structures, the iron centres adopt a "piano stool" distribution formed by the iron-Cp unit bound to one phosphine, one CO molecule, and one of different benzonitrile molecules. The C-O bond lengths are between 1.13-1.16 Å (see Table S1), and they decrease in the sequence p-H > p-NH2 > p-Br, which indicates that an increased contribution of resonance structure due to an increase in the character π-acceptor of the ligand and/or the effect of the electronegativity of p-substituent in benzonitrile molecules causes that the Fe back-bonding into the CO π* orbital is less important and the distance increases [24]. An increase of strong π-acceptor character in benzonitrile molecules, compete with CO molecule for the electron back-donation and the CO stretch frequencies remain high, as also observed by the FTIR stretching frequencies as well [25].…”

Section: Uv-vis Spectroscopymentioning

confidence: 99%

A New Family of Iron(II)-Cyclopentadienyl Compounds Shows Strong Activity against Colorectal and Triple Negative Breast Cancer Cells

et al. 2020

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A family of compounds with the general formula [Fe(η5-C5H5)(CO)(PPh3)(NCR)]+ has been synthesized (NCR = benzonitrile (1); 4-hydroxybenzonitrile (2); 4-hydroxymethylbenzonitrile (3); 4-aminobenzonitrile (4); 4-bromobenzonitrile (5); and, 4-chlorocinnamonitrile (6)). All of the compounds were obtained in good yields and were completely characterized by standard spectroscopic and analytical techniques. Compounds 1, 4, and 5 crystallize in the monoclinc P21/c space group and packing is determined by short contacts between the phosphane phenyl rings and cyclopentadienyl (compounds 1 and 4) or π-π lateral interactions between the benzonitrile molecules (complex 5). DFT and TD-DFT calculations were performed to help in the interpretation of the experimental UV-Vis. data and assign the electronic transitions. Cytotoxicity studies in MDA-MB-231 breast and SW480 colorectal cancer-derived cell lines showed IC50 values at a low micromolar range for all of the compounds in both cell lines. The determination of the selectivity index for colorectal cells (SW480 vs. NCM460, a normal colon-derived cell line) indicates that the compounds have some inherent selectivity. Further studies on the SW480 cell line demonstrated that the compounds induce cell death by apoptosis, inhibit proliferation by inhibiting the formation of colonies, and affect the actin-cytoskeleton of the cells. These results are not observed for the hydroxylated compounds 2 and 3, where an alternative mode of action might be present. Overall, the results indicate that the substituent at the nitrile-based ligand is associated to the biological activity of the compounds.

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“…The preparation of racemic aceto(carbonyl)(cyclo-pentadienyl)(triphenylphosphine)iron (2) was first reported in 1966. 2 Brunner subsequently recognized that the iron atom in the complex was a chiral center and first reported the preparation of the (+)-and (-)-enantiomers in 1972. 3 Two groups 4,5 , recognized in the early 1980s that the enolate of this compound might serve as a chiral acetate enolate equivalent.…”

Section: (S)-aceto(carbonyl)(cyclopentadienyl)-(triphenylphosphine)ironmentioning

confidence: 99%

(S)-Aceto(carbonyl)(cyclopentadienyl)-(triphenylphosphine)iron

Welker

2001

Encyclopedia of Reagents for Organic Synthesis

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Reactions of Cyclopentadienyl (methyl) iron Dicarbonyl with Various Ligands. Cyclopentadienyl(acetyl)iron Carbonyl Phosphine and Phosphite Complexes

Cited by 123 publications

References 1 publication

Synthesis of Main‐Chain Metal Carbonyl Organometallic Macromolecules (MCMCOMs)

Synthesis of Main‐Chain Metal Carbonyl Organometallic Macromolecules (MCMCOMs)

A New Family of Iron(II)-Cyclopentadienyl Compounds Shows Strong Activity against Colorectal and Triple Negative Breast Cancer Cells

(S)-Aceto(carbonyl)(cyclopentadienyl)-(triphenylphosphine)iron

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