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According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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Magnetically Induced Current Density in Nonplanar Fully Benzenoid Hydrocarbons.

Marija Antić1, Slađana Đorđević1, Boris Furtula1

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Molecular planarity impacts aromaticity in benzenoid hydrocarbons. Even nonplanar systems show accurate local aromaticity using Clar formulas, confirmed by studying magnetically induced current densities.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Quantum Chemistry

Background:

  • Previous work established Clar formulas' utility for local aromaticity in nonplanar benzenoid hydrocarbons.
  • Understanding molecular planarity's role in electronic properties is crucial for predicting chemical behavior.

Purpose of the Study:

  • To investigate the influence of molecular planarity on ab initio magnetically induced current densities in benzenoid hydrocarbons.
  • To rationalize planarity effects by analyzing the origins of induced current density.

Main Methods:

  • Calculations of ab initio magnetically induced current densities for series of increasingly planar benzenoid hydrocarbons.
  • Analysis of virtual transitions between occupied and unoccupied molecular orbitals to understand current density origins.

Main Results:

  • Molecular planarity significantly influences magnetically induced current densities.
  • The distribution of local aromaticity, even in nonplanar systems, is accurately described by Clar formulas.
  • Induced current densities can be rationalized by examining electronic transitions.

Conclusions:

  • Molecular planarity is a key factor affecting magnetic response in benzenoid systems.
  • Clar aromaticity concepts remain valid for assessing local aromaticity in nonplanar molecules.
  • The study provides insights into the relationship between molecular geometry and electronic aromaticity.