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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
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 Elevation03:12

Freezing Point Depression and Boiling Point Elevation

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 Fragmentation01:23

Mass Spectrometry: Aromatic Compound Fragmentation

Upon ionization, aromatic compounds generate a molecular ion that is observed as a prominent peak in their mass spectra. For example, the molecular ion peak for benzene appears at a mass-to-charge ratio of 78, while toluene is observed at a mass-to-charge ratio of 92. The molecular ion benzene is highly stable and does not readily undergo further fragmentation due to the significant amount of energy required to disrupt the aromatic stability of the benzene ring. In contrast, the molecular ion...
¹H NMR Signal Integration: Overview00:58

¹H NMR Signal Integration: Overview

The intensity of a signal, which can be represented by the area under the peak, depends on the number of protons contributing to that signal. The area under each peak is shown as a vertical line called an integral, with the integral value listed under it, as seen in the proton NMR spectrum of benzyl acetate. Each integral value is divided by the smallest integral value to obtain the ratio of the number of protons producing each signal. The ratio reveals the relative number of protons and not...

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Related Experiment Video

Updated: May 20, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

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.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 19, 2026
PubMed
Summary
This summary is machine-generated.

A molecular balance using cyclooctatetraene (COT) shows the folded 1,6-dibenzyl COT isomer is favored over the unfolded 1,4-isomer. This preference is driven by London dispersion interactions between aromatic groups in solution.

Keywords:
CH‐π InteractionsLondon dispersionnoncovalent interactionssolvent effectssteric effects

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Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry
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Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

Related Experiment Videos

Last Updated: May 20, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry
16:11

Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Computational Chemistry

Background:

  • Benzene dimer interactions are crucial in understanding non-covalent forces in organic systems.
  • Cyclooctatetraene (COT) derivatives offer unique conformational flexibility for studying such interactions.

Purpose of the Study:

  • To model and quantify benzene dimer interactions in solution using a dibenzyl-substituted COT molecular balance.
  • To investigate the conformational equilibrium between 1,4- and 1,6-dibenzyl COT isomers.

Main Methods:

  • Utilized a combination of experimental Nuclear Magnetic Resonance (NMR) spectroscopy and computational studies.
  • Analyzed the equilibrium between unfolded (1,4-) and folded (1,6-) dibenzyl COT isomers in various organic solvents.

Main Results:

  • The folded 1,6-dibenzyl COT isomer was consistently favored over the 1,4-isomer by approximately 0.3 kcal mol⁻¹.
  • This energetic preference was observed irrespective of the solvent used in the study.
  • Computational analysis identified London dispersion (LD) interactions as the primary stabilizing force in the 1,6-COT isomer.

Conclusions:

  • London dispersion forces play a significant role in stabilizing folded aromatic systems in solution.
  • The dibenzyl-substituted COT serves as an effective molecular model for probing non-covalent aromatic interactions.