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Ferrocene Orientation Determined Intramolecular Interactions Using Energy Decomposition Analysis.

Feng Wang1, Shawkat Islam2, Vladislav Vasilyev3

  • 1Molecular Model Discovery Laboratory, Department of Chemistry and Biotechnology, Faculty of Science, Engineering and Technology, Swinburne University of Technology, Hawthorn, Melbourne 3122, Australia. fwang@swin.edu.au.

Materials (Basel, Switzerland)
|August 11, 2017
PubMed
Summary
This summary is machine-generated.

Quantum mechanical energy decomposition analyses reveal Pauli repulsion and orbital attraction drive ferrocene conformation. Eclipsed ferrocene is preferred due to strong iron lone pair interactions with ligand antibonds.

Keywords:
eclipsed and staggered conformersenergy decomposition analysisferroceneintramolecular interactionnatural bond orbital schemequantum mechanical models

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Area of Science:

  • Quantum chemistry
  • Computational chemistry
  • Molecular modeling

Background:

  • Ferrocene exists in eclipsed and staggered conformations.
  • Understanding conformational preferences is crucial for predicting molecular properties and reactivity.
  • Previous studies have explored ferrocene's conformational stability with varying theoretical approaches.

Purpose of the Study:

  • To investigate the key energetic differences between eclipsed and staggered ferrocene conformers using two distinct quantum mechanical energy decomposition analysis (EDA) schemes.
  • To elucidate the contributions of Pauli repulsion and orbital interactions to the conformational stability of ferrocene.
  • To identify the dominant stabilizing interactions in the preferred ferrocene conformation.

Main Methods:

  • Utilized two energy decomposition analysis (EDA) schemes: Extended Transition State (ETS) from Amsterdam Density Functional (ADF) and Natural EDA (NEDA) from GAMESS.
  • Employed a complete fragment channel approach using individual neutral atoms as fragments to avoid artifacts.
  • Performed Natural Bond Orbital (NBO) analysis to further investigate electronic interactions.

Main Results:

  • Both ETS and NEDA schemes identified Pauli repulsive energy and orbital attractive energy as major contributors to the energy difference between conformers.
  • The NEDA scheme showed that attractive polarization (POL) and charge transfer (CL) energies favor the eclipsed conformer, while repulsive deformation (DEF) energy favors the staggered conformer.
  • A significant stabilization of -457.6 kcal·mol⁻¹ for the eclipsed ferrocene was attributed to interactions between iron lone pairs (LP) and antibonding orbitals (BD*) of the ligand's C-C and C-H bonds.

Conclusions:

  • The eclipsed ferrocene conformer is the energetically preferred structure due to a combination of quantum mechanical Pauli repulsion and orbital attraction.
  • Specific electronic interactions, particularly LP(Fe)-BD*(C-C & C-H), strongly stabilize the eclipsed conformation.
  • The choice of fragmentation channels in EDA is critical and can influence the calculated interaction energies.