Methylcyclopentadiene

Methylcyclopentadiene

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Identifiers
ChemSpider	60141 Y
Jmol 3D model	Interactive image
PubChem	66775
InChI InChI=1S/C6H8/c1-6-4-2-3-5-6/h2-4H,5H2,1H3 Y Key: NFWSQSCIDYBUOU-UHFFFAOYSA-N Y InChI=1/C6H8/c1-6-4-2-3-5-6/h2-4H,5H2,1H3 Key: NFWSQSCIDYBUOU-UHFFFAOYAV
SMILES C\1=C\C=C(\C)C/1
Properties
Chemical formula	C6H8
Molar mass	80.13 g·mol−1
Vapor pressure	{{{value}}}
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

Methylcyclopentadiene describes three isomeric cyclic dialkenes with the formula C₅MeH₅ (Me = CH₃). These isomers are the organic precursor to the methylcyclopentadienyl ligand (C₅H₄Me, often denoted as Cp′), commonly found in organometallic chemistry. C₅MeH₅ is prepared by thermal cracking its Diels–Alder dimer, followed by distillation to remove cyclopentadiene C₅H₆, a common impurity.

File:Cp'FeP(CO)I.png

Structure of Cp′Fe(PPh₃)(CO)I, with labels for the four diastereotopic ring protons.

Relative to the corresponding Cp complexes, complexes of Cp′ exhibit enhanced solubility in organic solvents. Furthermore, Cp′ is often employed to probe the structure of organometallic complexes. For example, Cp′Fe(PPh₃)(CO)I exhibits four MeC₅H₄ resonances in its ¹H NMR spectrum and five MeC₅H₄ resonances in the ¹³C NMR spectrum. Free rotation of the Cp′ ligand does not equivalence the diastereopic protons and carbon centers. The achiral precursor complex Cp′Fe(CO)₂)I exhibits only two MeC₅H₄ resonances in the ¹H NMR spectrum and three MeC₅H₄ resonances in the ¹³C NMR spectrum.

See also

• Cyclopentadiene
• Pentamethylcyclopentadiene