Related Experiment Video
Updated: May 20, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Assessing Benzene Dimer Interactions in Solution With a Molecular Balance
Marvin H J Domanski1, Michael Fuhrmann1, Nils F Hacket1
1Institute of Organic Chemistry, Justus Liebig University, Giessen, Germany.
None:
We present a combined experimental and computational study of a 1,4/1,6-dibenzyl substituted cyclooctatetraene (COT)-based molecular balance as a model to assess the benzene dimer interactions in solution. This is accomplished by investigating the equilibrium between the unfolded 1,4- versus folded 1,6-dibenzyl COT in a variety of common organic solvents. NMR measurements demonstrate that the 1,6-COT isomer, in which the phenyl moieties are in proximity, is always favored over the unfolded and sterically less hindered 1,4-COT by ∼0.3 kcal mol-1, irrespective of solvent. Computations identify London dispersion (LD) interactions between the aromatic moieties in 1,6-COT as the main stabilizing force.
Related Concept Videos
NMR Spectroscopy of Benzene Derivatives
Structure of Benzene: Molecular Orbital Model
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Freezing Point Depression and Boiling Point Elevation
The boiling point of a liquid is the temperature at which its vapor pressure is equal to ambient atmospheric pressure. Since the vapor pressure of a solution is lowered due to the presence of nonvolatile solutes, it stands to reason that the solution’s boiling point will subsequently be increased. Vapor pressure increases with temperature, and so a solution will require a higher temperature than will pure solvent to achieve any given vapor pressure, including one...
Mass Spectrometry: Aromatic Compound Fragmentation
¹H NMR Signal Integration: Overview
