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Quantitative model for rationalizing solvent effect in noncovalent CH-Aryl interactions.

Bright U Emenike1, Sara N Bey1, Brianna C Bigelow1

  • 1Department of Chemistry & Physics , State University of New York , 223 Store Hill Road, Old Westbury , NY 11568 , USA .

Chemical Science
|June 19, 2018
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Summary
This summary is machine-generated.

The strength of CH-aryl interactions was quantified using a molecular torsion balance across 14 solvents. Specific solvent properties, not just polarity, were found to significantly influence these interactions.

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Area of Science:

  • Supramolecular Chemistry
  • Physical Organic Chemistry
  • Computational Chemistry

Background:

  • CH-aryl interactions are crucial in molecular recognition and self-assembly.
  • Understanding solvation effects on these interactions is key to predicting molecular behavior.

Purpose of the Study:

  • To quantitatively measure the strength of CH-aryl interactions in various solvents.
  • To elucidate the role of specific solvent properties in modulating these interactions.

Main Methods:

  • Utilized a molecular torsion balance to analyze conformational preferences.
  • Employed linear solvation energy relationships (LSER) based on Kamlet-Taft parameters.
  • Performed DFT-D calculations for gas-phase interaction energy estimation.

Main Results:

  • Determined the Gibbs free energy (ΔG) of CH-aryl interactions in 14 solvents.
  • Found that solvent polarity alone was insufficient to explain observed effects.
  • Developed an LSER equation [ΔG = -0.24 + 0.23α - 0.68β - 0.1π* + 0.09δ] correlating ΔG with solvent properties (hydrogen-bond acidity α and basicity β).
  • Predicted a gas-phase ΔG of -0.31 kcal mol⁻¹, consistent with DFT-D calculations (-0.35 kcal mol⁻¹).

Conclusions:

  • Specific solvent effects, particularly hydrogen-bond acidity and basicity, are dominant in influencing CH-aryl interaction strength.
  • LSER provides a robust framework for predicting solvation effects on CH-aryl interactions.
  • The study offers insights into the design of molecules with tailored interaction strengths in solution and gas phases.