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In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
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Lewis Acid-Assisted Generation of Iodenium(I) Ions: A Computational Approach.

Anna V Pomogaeva1, Yana I Kulikova1, Alexey Y Timoshkin1

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|December 10, 2025
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Summary
This summary is machine-generated.

Lewis acids like antimony pentafluoride (SbF5) can generate iodonium cations from iodine (I2) and iodine monochloride (ICl). However, boratriptycenes are unsuitable for this due to stable complex formation.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Area of Science:

  • Computational Chemistry
  • Inorganic Chemistry
  • Theoretical Chemistry

Background:

  • Lewis acids are crucial for generating reactive intermediates.
  • Iodine (I2) and iodine monochloride (ICl) can serve as precursors for iodonium cations.
  • Understanding complexation behavior is key to controlling reactivity.

Purpose of the Study:

  • To computationally investigate Lewis acid-assisted generation of iodonium cations.
  • To evaluate the potential of SbX5 and bora/alatriptycenes as Lewis acids for iodonium cation synthesis.
  • To explore the influence of solvent effects on complex formation and reactivity.

Main Methods:

  • Density functional theory (DFT) calculations using M06-2X/def2-TZVP.
  • Gas-phase and solution-phase (SMD model) simulations.
  • Analysis of molecular and ionic complex formation.

Main Results:

  • Boratriptycenes form stable complexes with Lewis bases, hindering I2 and ICl complexation.
  • Halogenation of B-C/Al-C bonds by I2 and ICl is generally favorable, limiting bora/alatriptycene utility.
  • SbX5 systems, especially SbF5 with ICl in nonpolar solvents, show promise for generating iodonium cations (I3+, I2Cl+) via contact ion pairs.

Conclusions:

  • Bora/alatriptycenes are not ideal for generating iodonium cations due to strong Lewis base interactions.
  • Antimony halides (SbX5) are more promising Lewis acids for iodonium cation synthesis.
  • The SbF5-ICl system in weakly coordinating solvents is a potentially fruitful area for experimental investigation.