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Organometallic Chemistry

This document provides an introduction to organometallic chemistry. It defines organometallic compounds as those containing metal-carbon bonds and lists examples such as Grignard reagents and metal carbonyl complexes. Key concepts discussed include metal-carbon bonding, the hapticity of ligands, electron counting using the 18-electron rule, and common ligands such as alkyl, carbonyl, and pi-bonded organic groups. Hapticity refers to the number of ligand atoms bonded to the metal center, and is represented by the Greek letter eta. Electron counting treats ligands as neutral to determine the total electron count around the metal.

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2K views14 pages

Organometallic Chemistry

This document provides an introduction to organometallic chemistry. It defines organometallic compounds as those containing metal-carbon bonds and lists examples such as Grignard reagents and metal carbonyl complexes. Key concepts discussed include metal-carbon bonding, the hapticity of ligands, electron counting using the 18-electron rule, and common ligands such as alkyl, carbonyl, and pi-bonded organic groups. Hapticity refers to the number of ligand atoms bonded to the metal center, and is represented by the Greek letter eta. Electron counting treats ligands as neutral to determine the total electron count around the metal.

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Reine G
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INTRODUCTION TO

ORGANOMETALLIC
CHEMISTRY
Chem 102.2
19 October 2016
Moises Jerome Garrero
Organometallic Compounds
• An organometallic compound contains one or more
metal–carbon bonds
• Examples:
• Salts of alkali metals and alkynes (RC≡C–M+)
• Organomagnesium compounds: Grignard reagents
(RMgX)
• Organocopper compounds: e.g. Li+[CuMe2]–
• Sandwich compounds: e.g. ferrocene
• Metal carbonyl complexes: e.g. [Fe(CO)5]
Concepts in Organometallic
Chemistry
• Metal–carbon bonding
• Hapticity of ligands
• Electron counting
• Frontier orbitals: HOMO and LUMO
Hapticity
• Hapticity refers to the number of atoms in the ligand
that are directly bonded to the metal center
• Symbolized by η
• Example: A ligand with hapticity of 5 is referred to
as pentahapto- and is symbolized by η5-
Hapticities of Cyclopentadiene
Common Ligands
• Sigma-bonded alkyl and aryl ligands
Common Ligands
• Carbonyl ligands
Common Ligands
• Carbonyl ligands
Common Ligands
• Pi-bonded organic ligands
Metal–Ethene Bonding
Metal–Butadiene Bonding
Electron Counting
• Low oxidation state organometallic complexes tend to
obey the 18-electron rule
• When the total electron count is 18, the complex is
most likely stable
• For purposes of electron counting, we treat all ligands
as neutral
• So for metals, the electron count should be the number
of valence electrons for the neutral metal
• Example: Ti = 4, Fe = 8, Rh = 9
Number of Valence Electrons of
Ligands
No. of Valence Common Examples of Ligands
Electrons
1 H; terminal X, R or RO (η1)
2 CO, PR3, P(OR)3, η2-alkene, R2C:
3 η3-C3H5, RC (carbyne), μ-X
4 η4-diene and cyclobutadiene
5 η5-Cp, μ3-X
6 η6-Ar
Electron Counting
Give the electron count of the following complexes:
• [IrBr2(CH3)(CO)(PPh3)2]: 9 + 2 x 1 + 1 + 2 + 2 x 2 = 18
• [Cr(η5-C5H5)(η6-C6H6)]: 6 + 5 + 6 = 17
• [Fe(CO)5]: 8 + 5 x 2 = 18
• [(CO)2Rh(μ-Cl)2Rh(CO)2]
•

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