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Aromaticity in metallabenzenes.

Israel Fernández1, Gernot Frenking

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35043 Marburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 25, 2007
PubMed
Summary
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Metallabenzenes exhibit aromatic character, with pi bonding primarily from b1 orbitals, contributing to their stability. Their aromatic stabilization energies are comparable to benzene, though generally weaker, with no clear correlation to specific ligands or metals.

Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Aromaticity Studies

Background:

  • Metallabenzenes are organometallic compounds featuring a metal atom within a cyclic structure.
  • Understanding their electronic structure and bonding is crucial for predicting their chemical behavior and stability.
  • Aromaticity in these systems is a key property influencing their reactivity and properties.

Purpose of the Study:

  • To investigate the electronic structure and bonding in 21 metallabenzenes.
  • To quantify the pi-bonding strength and aromatic character of these compounds.
  • To compare their aromaticity with benzene and related acyclic molecules.

Main Methods:

  • Density Functional Theory (DFT) calculations using the BP86/TZ2P level of theory.

Related Experiment Videos

  • Energy Decomposition Analysis (EDA) to dissect interaction energies between fragments.
  • Calculation of aromatic stabilization energies (ASEs).

    • Main Results:

    • Metallabenzenes possess five occupied pi orbitals (two b1, three a2), forming 10 pi-electron systems.
    • Pi bonding is mainly driven by the b1 contribution, with a significant a2 contribution.
    • Calculated ASEs range from 8.7 to 37.6 kcal/mol, indicating significant aromaticity, though generally less than benzene (42.5 kcal/mol).
    • Classical metallabenzene models show intermediate aromaticity.
    • No clear correlation found between aromatic stabilization and specific ligands, metals, coordination numbers, or charge.

    Conclusions:

    • Metallabenzenes are aromatic compounds with aromatic stabilization energies approaching that of benzene.
    • The pi-electron system and orbital contributions are key to their aromatic character.
    • Factors like metal type (4d vs. 5d) or ligand environment do not show a direct correlation with the degree of aromatic stabilization.