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A preorganized hydrogen bond network and its effect on anion stability
Masoud Samet1, Xue-Bin Wang, Steven R Kass
1Department of Chemistry, University of Minnesota , Minneapolis, Minnesota 55455, United States.
The Journal of Physical Chemistry. A
|July 19, 2014
Summary
Researchers synthesized novel cyclohexanetriol derivatives and studied their electron binding energies. Trifluoromethyl groups and hydrogen bonding significantly stabilize anions, impacting electronic properties and molecular interactions.
Area of Science:
- Organic Chemistry
- Physical Chemistry
- Computational Chemistry
Background:
- Cyclohexanetriol derivatives offer a rigid scaffold for studying substituent effects.
- Anion photoelectron spectroscopy and computational methods are key to understanding electronic structures.
Purpose of the Study:
- Synthesize rigid cyclohexanetriol derivatives with varying trifluoromethyl groups.
- Characterize the electronic properties (VDE, ADE) of their conjugate bases and chloride anion clusters.
- Investigate the roles of hydrogen bonding and inductive effects in anion stabilization.
Main Methods:
- Synthesis of rigid 1,3,5-cyclohexanetriol derivatives.
- Photoelectron spectroscopy of conjugate bases and chloride anion clusters.
- Density functional theory (DFT) computations.
Main Results:
- Synthesized derivatives with 0-3 trifluoromethyl groups.
- Measured vertical detachment energies (VDE) and adiabatic detachment energies (ADE) for anions.
- Observed significant anion stabilization through hydrogen bonding and inductive effects.
- Quantified enhancement of ADEs by 1.61-2.88 eV (conjugate bases) and 1.01-1.60 eV (chloride clusters).
Conclusions:
- Hydrogen bonding and inductive effects, transmitted through space, are crucial for anion stabilization.
- Increased trifluoromethylation and ring oxygenation enhance anion stability.
- Complex structures with multiple hydrogen bonds to chloride ions are favored.
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