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The Synthesis of [Pd(mu-Cl)(C6H4N=NPh)]2

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Francisco J. Arnáiz

Laboratorio de Quimica Inorganica, Universidad de Burgos, 09001 Burgos, Spain

J. Chem. Educ., 1996, 73 (6), p A126

DOI: 10.1021/ed073pA126

Publication Date (Web): June 1, 1996

Section:

History, Education, and Documentation

Abstract

Bis-{mu-chloro-[2-(phenylazo-kN^2)-phenyl]palladium},[Pd(mu-Cl)(C6H4N=NPh)]2, is the prototype cyclo-metallated compound, and constitutes a good example to illustrate the ease of formation of some M-C alpha bonds along with their resistance to atmospheric agents. The compound was first obtained by A. C. Cope and R. W. Siekman 30 years ago, and since then many derivatives have been prepared, especially by cleaving the chlorine bridges with bases and by replacing them with a variety of ligands. In recent years, a number of closely related compounds have attracted considerable attention in the development of new organometallic liquid crystals.

A procedure for the synthesis of [Pd(mu-Cl)(C6H4N=NPh)]2 using palladium(II) chloride and azobenzene, via Li2[PdCl4], has been described recently. However, this procedure, which is followed widely to prepare a variety of cyclo-palladated compounds, requires six to eight hours when starting with PdCl2, and two to three hours if a solution of Li2[PdCl4] in methanol is available.

The procedure proposed in this article consists of reacting PdCl2 with azobenzene in dimethyl sulfoxide (DMSO) and is appropriate especially for the microscale laboratory because it offers some advantages with respect to previously reported procedures.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

A One-Pot Self-Assembly Reaction To Prepare a Supramolecular Palladium(II) Cyclometalated Complex: An Undergraduate Organometallic Laboratory Experiment
Alberto Fernández, Margarita López-Torres, Jesús J. Fernández, Digna Vázquez-García, and José M. Vila
Journal of Chemical Education2012 89 (1), 156-158
- A One-Pot Self-Assembly Reaction To Prepare a Supramolecular Palladium(II) Cyclometalated Complex: An Undergraduate Organometallic Laboratory Experiment
  Alberto Fernández, Margarita López-Torres, Jesús J. Fernández, Digna Vázquez-García, and José M. Vila
  Journal of Chemical Education2012 89 (1), 156-158
  A laboratory experiment for students in advanced inorganic chemistry is described. Students prepare palladium(II) cyclometalated complexes. A terdentate [C,N,O] Schiff base ligand is doubly deprotonated upon reaction with palladium(II) acetate in a self-...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Cyclopalladation of Phenyl-(2,4,6-trimethylbenzylidene)-amine: An Undergraduate Organometallic Laboratory Experiment
Joan Albert , Magali Cadena and Jaume Granell
Journal of Chemical Education2003 80 (7), 801
- Cyclopalladation of Phenyl-(2,4,6-trimethylbenzylidene)-amine: An Undergraduate Organometallic Laboratory Experiment
  Joan Albert , Magali Cadena and Jaume Granell
  Journal of Chemical Education2003 80 (7), 801
  The synthesis of a six-membered cyclopalladated complex by activation of a Caliphatic—H bond is reported. The synthesis of this organometallic compound is simple and does not require any special equipment, such as gas cylinders, vacuum lines, or solvents ...
  Abstract | Hi-Res PDF | PDF w/ Links