Organometallics are compounds with metal-carbon bonds; they are used in organic synthesis and industrial processes. This Demonstration shows the basic characteristics for 25 organometallic compounds: the complex, code-ID (for the crystallography open database)/csd-refcode (for the Cambridge structural database), formula, coordination number and polyhedron, DOI (digital object identifier for a publication), and three 3D views (molecule, molecule and polyhedron around the metal atom, and idealized polyhedron). You can also see a selection of milestones in organometallic chemistry.
Timeline with Milestones of Organometallic Chemistry
Organometallic chemistry began in France with Cadet's fluid (1760). A remarkable discovery was the first -complex, the Zeise salt (1827). The Grignard reagent had far-reaching consequences (NP 1912). The Fischer–Tropsch process was developed in Germany (1925). Pauson discovered a structure, later named ferrocene (1951). Ziegler and Natta developed catalyzed processes to produce polyolefins (1955). Fischer made the first carbene complex (1964). Shilov created the field of C-H activation (1969). Brookhart and Green introduced an intramolecular agostic C-H bond concept (1983). Kubas developed the first dihydrogen complex (1984). For their work on the olefin metathesis, Chauvin, Grubbs, and Schrock received the Nobel prize (2005) [1, 3].
There is a checkbox in the Demonstration to enable a timeline view with a selection of milestones in organometallic chemistry from 1760 to 2005.
The organometallic chemistry of transition metals can be organized according to the type of organic ligands bound to the central metal atom(s).
An incomplete list of ligands for complexes is: acyl, alkane, alkyne, amines, arene, carbene, carbide, carbonyl, carbyne, dihydrogen, dinitrogen, hydride, imines, isocyanide, nitrosyl, olefin, phosphine, pyridine, silane, tetrahydrofuran, thiocarbonyl, thioether, vinyl [3, 4].
Table of All Complexes Shown
This table shows the coordination polyhedra and coordination number from 2 to 6 for compounds of transition metals and includes the complexes in this Demonstration (inspired by ).
Short Description for Three of the 25 Complexes Shown
is a Fischer carbene complex containing two different transition metals. The 2-benzo[b]thienyl group is -bonded to a chromium tricarbonyl fragment. The molecular geometry for tungsten/chromium is octahedral/tetrahedral .
and react to titana acylborane . can either be or . The compound used in this Demonstration is the second case. It is a complex with a neutral oxygen donor. Titanium in this complex shows a tetrahedral molecular geometry .
The silyl -dihydrogen complex is the product of the reaction of the complex and . For the molecular geometry of ruthenium, the authors suggest a pseudo-octahedral molecular geometry .
Crystallography Open Database and CSD are the sources for the ball and stick figures. The code-IDs and CCDC refcodes for each structure used are listed in the Demonstration.
 D. Astruc, Organometallic Chemistry and Catalysis, New York: Springer, 2007.
 R. Crabtree, The Organometallic Chemistry of the Transition Metals, Hoboken, NJ: John Wiley & Sons, Inc., 2005.
 C. Elschenbroich, Organometallchemie, Wiesbaden: B. G. Teubner Verlag / GWV Fachverlage GmbH, 2008.
 J. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, Sausalito, CA: University Science Books, 2010.
 U. Müller, Inorganic Structural Chemistry, 2nd ed., Hoboken, NJ: John Wiley & Sons, 2006.
 D. Bezuidenhout, W. Barnard, B. van der Westhuizen, E. van der Watt, and D. Liles, "Multimetal Fischer Carbene Complexes of Group VI Transition Metals: Synthesis, Structure and Substituent Effect Investigation," Dalton Transactions, 40(25), 2011 pp. 6711–6721. doi:10.1039/C1DT10183H.
 R. Choukroun, C. Lorber, C. Lepetit, and B. Donnadieu, "Reactivity of and : Formation of the Acylborane Complexes and ," Organometallics, 22(10), 2003 pp. 1995–1997. doi:10.1021/om030185t.
 S. Lachaize, A. Caballero, L. Vendier, and S. Sabo-Etienne, "Activation of Chlorosilanes at Ruthenium: A Route to Silyl -Dihydrogen Complexes," Organometallics, 26(15), 2007 pp. 3713–3721. doi:10.1021/om700295g.