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Related Concept Videos

Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.1K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.8K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.8K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.9K
Mass Spectrometry: Aromatic Compound Fragmentation01:23

Mass Spectrometry: Aromatic Compound Fragmentation

1.9K
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...
1.9K
¹H NMR: Complex Splitting01:13

¹H NMR: Complex Splitting

1.3K
A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied...
1.3K

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The limit of the current aromaticity concept.

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Nucleus Independent Chemical Shift (NICS) at Small Distances from the Molecular Plane: The Effect of Electron Density.

Chemphyschem : a European journal of chemical physics and physical chemistry·2023
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Dimorpholinoacetylene and Its Use for the Synthesis of Tetraaminocyclobutadiene Species.

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The Aromatic Character of Diindeno[2,1-<i>b</i>:2',1'-<i>h</i>]biphenylene.

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Practical Aspects of Sample Preparation and Setup of 1H R1&#961; Relaxation Dispersion Experiments of RNA
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Singlet Fission and Aromaticity.

Amnon Stanger1

  • 1Schulich Department of Chemistry, Technion, Haifa 3200003, Israel.

The Journal of Physical Chemistry. A
|October 24, 2022
PubMed
Summary

Magnetic aromaticity can predict singlet fission (SF) properties in organic molecules. Global and local ring currents indicate SF ability, aiding in the screening of new SF materials.

Area of Science:

  • Computational chemistry
  • Organic electronics
  • Materials science

Background:

  • Aromaticity-based arguments are commonly used to explain singlet fission (SF) properties in conjugated systems.
  • Magnetically induced ring currents correlate with molecular orbital transitions, suggesting a link to electronic state energies relevant for SF.

Purpose of the Study:

  • To investigate the relationship between quantitative magnetic aromaticity and singlet fission (SF) properties.
  • To determine if induced ring currents can serve as indicators for SF capability in various organic molecules.

Main Methods:

  • Utilized nucleus-independent chemical shift (NICS)-XY scan methods to assess quantitative aromaticity.
  • Studied closed-shell singlet, open-shell singlet, and triplet electronic states of oligoacenes and boron-doped anthracenes/phenanthrenes.

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Main Results:

  • Quantitative magnetic aromaticity successfully identified SF compounds for initial screening.
  • Global and local ring currents were identified as key indicators of singlet fission (SF) ability.
  • The findings were validated across diverse SF systems, including quinones, benzofurans, and cibalackrot.

Conclusions:

  • Magnetic aromaticity, specifically global and local ring currents, is a reliable indicator for predicting singlet fission (SF) properties.
  • This approach offers a valuable tool for the initial screening of potential SF materials.
  • Predicted SF properties for novel boron-doped phenylenes.