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Dissecting the single-electron C-C bond: NBO and AIM perspectives.

Leonardo I Lugo-Fuentes1, Darien I Martínez-Valencia1, J Oscar C Jiménez-Halla1

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The C1-C2 interaction in spiro-dibenzocycloheptatriene is a weak, delocalized van der Waals force, not a single electron sigma bond. Electronic structure analysis confirms limited bond character and low interaction energy.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Spiro-dibenzocycloheptatriene (1p) is a tricyclic compound with a unique oxidation product.
  • The interaction between ipso carbon atoms (C1 and C2) has been proposed as a single electron sigma C-C bond.

Purpose of the Study:

  • To perform a comprehensive electronic structure analysis of the oxidation product of spiro-dibenzocycloheptatriene (1p).
  • To characterize the nature of the non-covalent interaction between ipso carbon atoms (C1 and C2).
  • To determine if the C1-C2 interaction can be classified as a single electron sigma bond.

Main Methods:

  • Non-covalent interaction (NCI) analysis.
  • Atoms in Molecules (AIM) theory.
  • Natural Bond Orbital (NBO) and Natural Resonance Theory (NRT) analyses.
  • Spin density population analysis.
  • NBO deletion analysis.

Main Results:

  • NCI analysis indicates a weak, predominantly van der Waals interaction between the tricyclic moieties.
  • AIM theory reveals a bond critical point between C1 and C2, but with low electron density.
  • Laplacian density contour shows charge depletion between C1-C2, unlike the charge accumulation in a typical sigma bond.
  • NBO analysis shows a minimal contribution of a single-electron sigma bond, with a natural bond order of 0.066 for C1-C2.
  • The C1-C2 interaction contributes only ~9.5% to the total pi-pi interaction energy.

Conclusions:

  • The C1-C2 interaction is a weak, highly delocalized interaction, not a single electron sigma bond.
  • The interaction is governed by subtle electronic effects, primarily van der Waals forces and donor-acceptor interactions.
  • The findings challenge the previous characterization of the C1-C2 bond.