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Sodium cyclopentadienide information


Sodium cyclopentadienide

The cyclopentadienide anion
Names
Preferred IUPAC name
Sodium cyclopentadienide
Other names
Sodium cyclopentadienylide, Cyclopentadienylsodium
Identifiers
CAS Number
  • 4984-82-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 71032 checkY
ECHA InfoCard 100.023.306 Edit this at Wikidata
EC Number
  • 225-636-8
PubChem CID
  • 78681
CompTox Dashboard (EPA)
  • DTXSID9063665 Edit this at Wikidata
InChI
  • InChI=1S/C5H5.Na/c1-2-4-5-3-1;/h1-5H;/q-1;+1 checkY
    Key: OHUVHDUNQKJDKW-UHFFFAOYSA-N checkY
  • InChI=1S/C5H5.Na/c1-2-4-5-3-1;/h1-5H;/q-1;+1
  • Key: OHUVHDUNQKJDKW-UHFFFAOYSA-N
SMILES
  • [Na+].c1[cH-]ccc1
Properties
Chemical formula
C5H5Na
Molar mass 88.085 g·mol−1
Appearance colorless solid
Density 1.113 g/cm3
Solubility in water
decomposition
Solubility THF
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp is the cyclopentadienide anion.[1] Sodium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities.[2]

  1. ^ International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. p. 262. Electronic version.
  2. ^ Cite error: The named reference Roesky was invoked but never defined (see the help page).

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Sodium cyclopentadienide

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Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp− is the cyclopentadienide...

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Organosodium chemistry

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importance is sodium cyclopentadienide. Sodium tetraphenylborate can also be classified as an organosodium compound since in the solid state sodium is bound...

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Sodium

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anions). Some well-known derivatives include sodium cyclopentadienide (NaC5H5) and trityl sodium ((C6H5)3CNa). Sodium naphthalene, Na+[C10H8•]−, a strong reducing...

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Lithium cyclopentadienide

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common reagent for the preparation of cyclopentadienyl complexes. Sodium cyclopentadienide Reent Michel; Regine Herbst-Irmer; Dietmar Stalke (2011). "Revealing...

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Ferrocene

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original transmetalation sequence using either commercially available sodium cyclopentadienide or freshly cracked cyclopentadiene deprotonated with potassium...

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Cyclopentadiene

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typically sodium hydride, sodium metal, and butyl lithium. Salts of this anion are commercially available, including sodium cyclopentadienide and lithium...

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Yttrocene

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can be obtained by reacting anhydrous yttrium(III) chloride and sodium cyclopentadienide in tetrahydrofuran. It decomposes when exposed to water to produce...

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Plumbocene

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commercially available. It may be synthesized by the reaction of sodium cyclopentadienide with a lead(II) source such as lead(II) nitrate or lead(II) iodide...

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Alkali metal

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importance is sodium cyclopentadienide. Sodium tetraphenylborate can also be classified as an organosodium compound since in the solid state sodium is bound...

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Aromatization

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the aromatic conjugate base cyclopentadienyl anion, isolable as sodium cyclopentadienide: 2 Na + 2 C5H6 → 2 NaC5H5 + H2 Aromatization can entail removal...

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Scandocene

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can be obtained by reacting anhydrous scandium(III) chloride and sodium cyclopentadienide in tetrahydrofuran. If scandium(III) fluoride and magnesocene are...

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Organolead chemistry

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110 °C and density 1.995 g/cm3. Reaction of a lead(II) source with sodium cyclopentadienide gives the lead metallocene, plumbocene. Certain arene compounds...

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Cyclopentadienyl complex

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compounds with transition metal chlorides. Sodium cyclopentadienide (NaCp) and lithium cyclopentadienide are commonly used. Trimethylsilylcyclopentadiene...

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Chromium hexacarbonyl

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Fischer carbene complexes: Treatment of chromium hexacarbonyl with sodium cyclopentadienide gives Na+[Cr(CO)3(C5H5)]−. Oxidation of this salt affords...

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Sodium compounds

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anions). Some well-known derivatives include sodium cyclopentadienide (NaC5H5) and trityl sodium ((C6H5)3CNa). Sodium naphthalene, Na+[C10H8•]−, a strong reducing...

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Hafnium tetrachloride

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HfCl4 → (C6H5CH2)4Hf + 4 MgCl2 Similarly, salt metathesis with sodium cyclopentadienide gives hafnocene dichloride: 2 NaC5H5 + HfCl4 → (C5H5)2HfCl2 + 2...

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Molybdocene dihydride

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compound is prepared by combining molybdenum pentachloride, sodium cyclopentadienide, and sodium borohydride. The dihydride converts to molybdocene dichloride...

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Metal halides

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halides generally have very high lattice energies. For example, sodium cyclopentadienide reacts with ferrous chloride to yield ferrocene: 2 NaC5H5 + FeCl2...

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Titanocene dichloride

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tetrachloride. The original synthesis by Wilkinson and Birmingham, using sodium cyclopentadienide, is still commonly used: 2 NaC5H5 + TiCl4 → (C5H5)2TiCl2 + 2 NaCl...

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Cobaltocene

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prepared by the reaction of sodium cyclopentadienide (NaC5H5) with anhydrous cobalt(II) chloride in THF solution. Sodium chloride is cogenerated, and...

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Metallocene

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compounds: Sodium cyclopentadienide (NaCp) is the preferred reagent for these types of reactions. It is most easily obtained by the reaction of molten sodium and...

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Tungsten hexacarbonyl

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kinetically more robust. Treatment of tungsten hexacarbonyl with sodium cyclopentadienide followed by oxidation of the resulting NaW(CO)3(C5H5) gives...

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Tantalocene trihydride

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pentachloride was added to a solution of sodium cyclopentadienide in tetrahydrofuran and an excess of sodium borohydride with yields reaching 60%, although...

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NACP

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Agency on Corruption Prevention, a government agency in Ukraine Sodium cyclopentadienide (NaCp), a chemical compound This disambiguation page lists articles...

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Organotantalum chemistry

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derivatives. These arise from the salt metathesis reactions of sodium cyclopentadienide and tantalum pentachloride. An example of this is the first transition...

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