Cyclopentadienyl allyl palladium

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Cyclopentadienyl allyl palladium
Cyclopentadienyl allyl palladium.png
Allyl(cyclopentadienyl)nickel(II)-3D-balls.png
Names
Other names
(Cp)Pd(allyl)
Identifiers
ChemSpider
PubChem CID
  • 57347372  PubChem has erroneous structure
Properties
C8H10Pd
Molar mass 212.59 g·mol−1
AppearanceReddish needle-shaped solid
Melting point 60 to 62 °C (140 to 144 °F; 333 to 335 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclopentadienyl allyl palladium is an organopalladium compound with formula (C5H5)Pd(C3H5). This reddish solid is volatile with an unpleasant odor. It is soluble in common organic solvents. The molecule consists of a Pd centre sandwiched between a Cp and allyl ligands. [1]

Contents

Preparation

This complex is produced by the reaction of allylpalladium chloride dimer with sodium cyclopentadienide: [1] [2]

2 C5H5Na + (C3H5)2Pd2Cl2 → 2 (C5H4)Pd(C3H5) + 2 NaCl

Structure and reactions

The 18-electron complex adopts a half-sandwich structure with Cs symmetry, i.e., the molecule has a plane of symmetry. The complex can be decomposed readily by reductive elimination.

C3H5PdC3H5 → Pd(0) + C5H5C3H5

The compound readily reacts with alkyl isocyanides to produce clusters with the approximate formula [Pd(CNR)2]n. It reacts with bulky alkyl phosphines to produce two-coordinated palladium(0) complexes: [3]

CpPd(allyl) + 2 PR3 → Pd(PR3)2 + C5H5C3H5

The compound has been used to deposit thin film chemical vapor deposition of metallic palladium. [4] [5]

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5
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References

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  2. R. B. King (1963). "Organometallic Chemistry of the Transition Metals. Organometallic Chemistry of the Transition Metals. III. Reactions between Sodium Cyclopentadienide and Certain Complex Transition Metal Halides". Inorg. Chem. 2 (3): 528. doi:10.1021/ic50007a026.
  3. Otsuka, S.; Yoshida, T.; Matsumoto, M.; Nakatsu, K. J. (1976). "Cyclohexyneplatinum(0) Complexes Containing Di-t-butylphenylphosphine, t-butyldiphenylphosphine or Trimethylphosphine". Australian Journal of Chemistry . 45 (1): 135–142. doi:10.1071/CH9920135.
  4. Y. G Kim; S. Bialy; R.W. Miller; J. T. Spencer; Dowben A. Peter; Datta S. (1989). "Selective area deposition of conducting palladium films on polyimide resins". Mater. Res. Soc. Symp. Proc. 158: 103–7. doi:10.1557/PROC-158-103. S2CID   97425013.
  5. K. Rajalingam; T. Strunskus; A. Terfort; R. A. Fischer; C. Wo (2008). "Metallization of a thiol-terminated organic surface using chemical vapor deposition". Langmuir . 24 (15): 7886–7994. doi:10.1021/la8008927. PMID   18590295.