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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as annulenes. In...
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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.

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Related Experiment Video

Updated: May 16, 2026

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry
12:08

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Published on: March 18, 2012

Aromatic stacking interactions in flavin model systems.

Vikas Nandwana1, Ifor Samuel, Graeme Cooke

  • 1Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, United States.

Accounts of Chemical Research
|November 21, 2012
PubMed
Summary
This summary is machine-generated.

Flavins are versatile molecules with tunable properties, crucial for biological redox processes and promising for organic electronics. This study explores how aromatic stacking influences flavin redox behavior in synthetic systems, mimicking enzyme function.

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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade

Published on: August 14, 2019

Related Experiment Videos

Last Updated: May 16, 2026

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry
12:08

Monitoring the Reductive and Oxidative Half-Reactions of a Flavin-Dependent Monooxygenase using Stopped-Flow Spectrophotometry

Published on: March 18, 2012

Fluorescence Anisotropy as a Tool to Study Protein-protein Interactions
10:44

Fluorescence Anisotropy as a Tool to Study Protein-protein Interactions

Published on: October 21, 2016

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
09:50

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade

Published on: August 14, 2019

Area of Science:

  • Biochemistry and Supramolecular Chemistry
  • Organic Electronics and Materials Science

Background:

  • Flavins are essential redox cofactors in numerous biological processes, including DNA repair and photosynthesis.
  • Their tunable optical, electronic, and redox properties are key to their function.
  • Flavins show potential in organic electronics as photoactive electron carriers.

Purpose of the Study:

  • To investigate the role of aromatic stacking in modulating flavin redox properties.
  • To gain insights into flavoenzyme function through synthetic host-guest systems.
  • To explore the development of novel flavin-based optoelectronic materials.

Main Methods:

  • Creation of host-guest systems using small molecule, polymer, and nanoparticle scaffolds.
  • Design of synthetic flavin-based interlocked structures.
  • Utilizing aromatic stacking to direct self-assembly of flavin-based materials.

Main Results:

  • Demonstrated that aromatic stacking significantly influences flavin redox properties.
  • Provided synthetic models that mimic flavoenzyme cofactor binding and regulation.
  • Showcased the potential of flavin-receptor assemblies for organic optoelectronics.

Conclusions:

  • Aromatic stacking is critical for both biological flavin activity and synthetic material design.
  • Synthetic models offer valuable insights into flavoenzyme mechanisms.
  • Flavin-based supramolecular assemblies hold promise for advanced optoelectronic applications.