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Cyclopentadienyl anion information


Cyclopentadienyl anion
Names
IUPAC name
Cyclopentadienide
Identifiers
CAS Number
  • 12127-83-2
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2731064
PubChem CID
  • 3490527
CompTox Dashboard (EPA)
  • DTXSID601027108 Edit this at Wikidata
InChI
  • InChI=1S/C5H5/c1-2-4-5-3-1/h1-5H/q-1
    Key: SINKOGOPEQSHQD-UHFFFAOYSA-N
  • InChI=1/C5H5/c1-2-4-5-3-1/h1-5H/q-1
    Key: SINKOGOPEQSHQD-UHFFFAOYAD
SMILES
  • [cH-]1cccc1
Properties
Chemical formula
[C
5
H
5
]
or Cp
Molar mass 65.09 g/mol
Conjugate acid Cyclopentadiene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of [C
5
H
5
]
and abbreviated as Cp.[1] It is formed by the deprotonation of cyclopentadiene. The cyclopentadienyl anion is a ligand which binds to a metal in organometallic chemistry.[2]

  1. ^ "Cyclopentadienide". PubChem Compound Database. National Center for Biotechnology Information. Retrieved 14 April 2016.
  2. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 66, ISBN 978-0-471-72091-1

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Cyclopentadienyl anion

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In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of [C 5H 5]− and abbreviated as Cp−. It is formed by...

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Cyclopentadienyl

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Cyclopentadienyl can refer to Cyclopentadienyl anion, or cyclopentadienide, [C 5H 5]− Cyclopentadienyl ligand Cyclopentadienyl radical, [C 5H 5]• Cyclopentadienyl...

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Cyclopentadiene

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with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−. This colorless liquid has a strong and unpleasant...

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Cyclopentadienyl radical

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chemistry, cyclopentadienyl is a radical with the formula C5H5. The related cyclopentadienyl anion (which can formally be converted to the cyclopentadienyl radical...

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Metallocene

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A metallocene is a compound typically consisting of two cyclopentadienyl anions (C 5H− 5, abbreviated Cp) bound to a metal center (M) in the oxidation...

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Rhodocene

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rhodocenes, all of which are unstable. The original synthesis used a cyclopentadienyl anion and tris(acetylacetonato)rhodium(III); numerous other approaches...

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Ferrous

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organometallic compounds, such as the ferrocene [Fe(C2H5)2], where two cyclopentadienyl anions are bound to the FeII centre. All known forms of life require iron...

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Boratabenzene

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is the heteroaromatic anion with the formula [C5H5BH]−. Derivatives of boratabenzene are ligands akin to cyclopentadienyl anion. sandwich or half-sandwich...

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Cyclopentane

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the hydrogen atoms (something which does not happen in the planar cyclopentadienyl anion C5H−5 because it doesn't have as many hydrogen atoms). This means...

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Ferrocene

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the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings sandwiching a central iron atom. It is an orange solid with a...

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Oxidation state

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oxidation state of 0 in one structure and −1 in the other. For the cyclopentadienyl anion C 5H− 5, the oxidation state of C is −1 + −1/5 = −6/5. The −1 occurs...

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Aromaticity

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found in ions as well: the cyclopropenyl cation (2e system), the cyclopentadienyl anion (6e system), the tropylium ion (6e), and the cyclooctatetraene dianion...

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Diene

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pentadienyl anion. An even greater effect is seen if the anion is aromatic, for example, deprotonation of cyclopentadiene to give the cyclopentadienyl anion. Dienes...

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Functional group

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-um. Examples are tropylium and triphenylmethyl cations and the cyclopentadienyl anion. Haloalkanes are a class of molecule that is defined by a carbon–halogen...

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Cyclooctatetraenide anion

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structure can serve as a ligand with various metals. Tropylium ion Cyclopentadienyl anion Jug, Karl (November 1984). "Aromaticity in unusual heteropolar monocyclic...

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Dicarbollide

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ortho-carborane. These dianions function as ligands, related to the cyclopentadienyl anion. Substituted dicarbollides are also known such as [C2B9H10(pyridine)]−...

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Azulene

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explained by regarding azulene as the fusion of a 6 π-electron cyclopentadienyl anion and a 6 π-electron tropylium cation: one electron from the seven-membered...

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Pentadiene

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chemistry, the pentadienyl anion is a ligand, the acyclic analogue of the more-common cyclopentadienyl anion. The pentadienyl anion is generated by deprotonation...

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Bismuth subhalides

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aromatic cyclopentadienyl aromatic anion. Contrary to the π-type all in-phase orbital overlap exhibited by the organic cyclopentadienyl anion, σ-type bonding...

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Aromatization

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cyclopentadiene, proton removal gives the aromatic conjugate base cyclopentadienyl anion, isolable as sodium cyclopentadienide: 2 Na + 2 C5H6 → 2 NaC5H5...

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Molecular symmetry

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octachlorodimolybdate(II) anion Trans-[CoIII(NH3)4Cl2]+ (excluding H atoms) D5h E 2C5 2C52 5C2 σh 2S5 2S53 5σv pentagonal cyclopentadienyl anion ruthenocene C70...

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Methylcyclopentadiene

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methylcyclopentadienyl anion. This ion is useful as a ligand for organometallic complexes. Relative to the corresponding cyclopentadienyl (Cp) complexes, complexes...

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Arenium ion

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then with triethylamine hydrolyzes the ether group. Aryl radical Cyclopentadienyl anion Meisenheimer complex, the analogous intermediate in nucleophilic...

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Sodium cyclopentadienide

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cyclopentadienide is also used for the preparation of substituted cyclopentadienyl derivatives such as the ester and formyl derivatives: NaC5H5 + O=C(OEt)2...

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Antiaromaticity

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Examples of antiaromatic compounds are pentalene (A), biphenylene (B), cyclopentadienyl cation (C). The prototypical example of antiaromaticity, cyclobutadiene...

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Nickelocene

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has a formal +2 charge, and the Cp rings are usually assigned as cyclopentadienyl anions (Cp−), related to cyclopentadiene by deprotonation. The structure...

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Carbanion

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at 6.5 ppm and two methylene bridge protons at 3 ppm whereas the cyclopentadienyl anion has a single resonance at 5.50 ppm. The use of 6Li and 7Li NMR has...

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