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Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Partially fluorinated butatrienes: a coupled cluster study.

Christian Ehm1, Dieter Lentz

  • 1Institut für Chemie und Biochemie, Abt. Anorganische Chemie, Freie Universität Berlin, 14195 Berlin, Germany.

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Fluorine substitution in butatrienes and butenyne isomers impacts molecular geometry and stability. Acetylenic fluorine significantly stabilizes butenyne isomers, with trifluoro-but-1-en-3-yne being more stable than its butatriene counterpart.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Quantum Chemistry

Background:

  • Butatrienes and butenyne isomers are important organic molecules.
  • Fluorine substitution can significantly alter molecular properties.

Purpose of the Study:

  • To investigate the impact of fluorine substitution on the geometries and energies of partially fluorinated butatrienes and butenyne isomers.
  • To determine the stability trends of these isomers with increasing fluorination.

Main Methods:

  • Calculations performed using Møller-Plesset second order perturbation theory with Dunning's valence triple-zeta basis set.
  • Final energies obtained at the Coupled Cluster Singles Doubles and Triples (CCSD(T))/cc-pVQZ level of theory.

Main Results:

  • Fluorine substitution has a minor effect on bond lengths but a significant effect on bond angles, leading to angle strain in some butatrienes.
  • Isomerization energies are substantially affected by fluorination, with acetylenic fluorine playing a crucial role.
  • The energy difference between butenyne and butatriene isomers decreases with increasing fluorination.

Conclusions:

  • Partially fluorinated butatrienes can exhibit angle strain due to fluorine substitution.
  • Fluorine substitution, particularly at the acetylenic center, significantly influences the relative stability of butatriene and butenyne isomers.
  • 1,1,4-trifluoro-but-1-en-3-yne is uniquely more stable than its butatriene isomer, highlighting the profound effect of acetylenic fluorination.