Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.6K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

3.9K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
3.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.6K
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...
2.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.1K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.1K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

9.9K
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...
9.9K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

7.3K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
7.3K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

p<i>K</i><sub>a</sub> Predicting Models Trained with a Tautomer-Compatible Graph Dataset with Quantum Chemical Features.

Journal of chemical information and modeling·2026
Same author

The relationship between postpartum care uptake and postpartum morbidity and their determinants in Morocco: a secondary analysis of a national survey.

BMC public health·2026
Same author

Regiodivergence in the Cycloadditions between a Cyclic Nitrone and Carbonyl-Type Dipolarophiles.

The Journal of organic chemistry·2025
Same author

Multifactorial determinants of postpartum care uptake in low- and middle-income countries: A systematic review and meta-analysis.

Midwifery·2025
Same author

Microfluidic Photocatalytic Ring Expansion of Sulfonium Salts for the Synthesis of Cyclic Sulfides.

ACS catalysis·2025
Same author

Crystallization-induced diastereomer transformation assists the diastereoselective synthesis of 4-nitroisoxazolidine scaffolds.

Organic & biomolecular chemistry·2024

Related Experiment Video

Updated: May 16, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

16.9K

Unusual Rearrangement of a 1,8-Naphthalene Derivative.

Asmaa Habib1, Estela Sánchez-Santos1, Irene Boya Del Teso1

  • 1Organic Chemistry Department, University of Salamanca, Plaza de los Caídos s/n, Salamanca 37008, Spain.

The Journal of Organic Chemistry
|April 3, 2025
PubMed
Summary

Steric strain in a nitro-naphthoic acid derivative unexpectedly breaks naphthalene aromaticity. Water addition triggers a reaction cascade, forming a conjugated aldehyde via intermediate fragmentation and rearrangement.

More Related Videos

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.4K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K

Related Experiment Videos

Last Updated: May 16, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

16.9K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.4K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Aromaticity Studies

Background:

  • Naphthalene derivatives are crucial in organic synthesis.
  • Understanding steric strain effects is key to predicting reactivity.
  • Aromaticity disruption can lead to novel chemical transformations.

Purpose of the Study:

  • To investigate the impact of steric strain on naphthalene aromaticity.
  • To elucidate the reaction mechanism of an 8-nitro-1-naphthoic acid derivative.
  • To characterize key intermediates and the final product.

Main Methods:

  • Synthesis of a strained 8-nitro-1-naphthoic acid derivative.
  • Reaction monitoring under mild conditions with water addition.
  • Characterization of intermediates using spectroscopic methods.
  • X-ray crystallography of the derivative.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Unexpected disruption of naphthalene aromaticity due to steric strain.
  • Identification of a naphtho oxazinium intermediate.
  • Fragmentation of a Csp2-Csp2 bond and rearrangement.
  • Formation of a conjugated aldehyde product.
  • DFT studies confirmed the proposed reaction pathway.

Conclusions:

  • Steric strain can overcome aromatic stabilization in naphthalene systems.
  • A novel reaction pathway involving aromaticity disruption and rearrangement has been identified.
  • The study provides insights into the reactivity of strained aromatic compounds.