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Can Electron-Rich π Systems Bind Anions?

Inacrist Geronimo1, N Jiten Singh1, Kwang S Kim1

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This summary is machine-generated.

This study reveals that anions can favorably bind to aromatics with negative quadrupole moments, challenging previous assumptions. This interaction is stabilized by induction effects, particularly with longer, unsaturated, or halogenated substituents.

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Area of Science:

  • Computational chemistry
  • Molecular interactions
  • Quantum chemistry

Background:

  • Anion-π interactions are typically observed between anions and aromatics with positive quadrupole moments.
  • Anions interacting with aromatics possessing negative quadrupole moments are generally expected to be unstable due to Coulombic repulsion.

Purpose of the Study:

  • To investigate the stability and nature of anion-π interactions with aromatics exhibiting negative quadrupole moments.
  • To explore the binding of halides to electron-rich substituted benzenes and triphenylene.

Main Methods:

  • Coupled cluster theory with singles, doubles, and perturbative triples excitations [CCSD(T)] at the complete basis set (CBS) limit was employed.
  • Symmetry adapted perturbation theory (SAPT) was used for energy decomposition analysis.

Main Results:

  • Favorable binding was demonstrated between anions (halides) and aromatics with negative quadrupole moments.
  • Binding stability increases with substituent chain length, unsaturation, and halogenation.
  • Electrostatic repulsion is overcome by significant induction effects from alkyl substituents.

Conclusions:

  • Anion-π interactions can be favorable even with aromatics possessing negative quadrupole moments.
  • Induction effects play a crucial role in stabilizing these interactions, counteracting Coulombic repulsion.
  • The findings expand the understanding of non-covalent interactions in chemistry and materials science.