Difference between revisions 6001774 and 6001775 on simplewiki

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(contracted; show full).1021/cr940053x| pmid=11848774|issue=2}}</ref> Substituents on the cyclopentadienyl ligands alters the redox potential in the expected way: electron-withdrawing groups such as a [[carboxylic acid]] shift the potential in the [[anodic]] direction (''i.e.'' made more positive), whereas electron-releasing groups such as [[methyl]] groups shift the potential in the [[Cathode|cathodic]] direction (more negative). Thus, [[decamethylferrocene]] is much more easily oxidised than ferrocene
. and can even be oxidised to the corresponding dication.<ref>{{Cite journal|last=Malischewski|first=M.|last2=Adelhardt|first2=M.|last3=Sutter|first3=J.|last4=Meyer|first4=K.|last5=Seppelt|first5=K.|date=2016-08-12|title=Isolation and structural and electronic characterization of salts of the decamethylferrocene dication|url=http://science.sciencemag.org/content/353/6300/678|journal=Science|language=en|volume=353|issue=6300|pages=678–682|doi=10.1126/science.aaf6362|issn=0036-8075|pmid=27516596}}</ref> Ferrocene is often used as an [[internal standard]] for calibrating redox potentials in non-aqueous [[electrochemistry]].

==Stereochemistry==
[[Image:Planar chiral ferrocene derivative.svg|thumb|right|A planar chiral ferrocene derivative]]
(contracted; show full)
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[[Category:Organoiron compounds]]
[[Category:Metallocenes]]
[[Category:Antiknock agents]]
[[Category:Sandwich compounds]]
[[Category:Cyclopentadienyl complexes]]