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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...

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Updated: Jun 1, 2026

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

2-(Naphthalen-2-yl)azulene.

Jian Ye1, Zi-Fa Shi, Chun-Lin Sun

  • 1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and, Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a novel compound linking naphthalene and azulene units. Its non-planar molecules pack in a herringbone arrangement, stabilized by weak C-H⋯π interactions.

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the structure-property relationships of polycyclic aromatic hydrocarbons is crucial.
  • Azulene and naphthalene are fundamental building blocks in organic electronics and materials science.
  • The synthesis and characterization of novel conjugated systems offer insights into their potential applications.

Purpose of the Study:

  • To elucidate the crystal structure of a compound formed by linking naphthalene and azulene units.
  • To analyze the molecular geometry, including planarity and dihedral angles.
  • To investigate the intermolecular interactions and packing motifs in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of molecular geometry involved calculating root-mean-square deviations from planarity.
  • Intermolecular interactions were identified through the analysis of C-H⋯π contacts.

Main Results:

  • The title compound, C(20)H(14), features a naphthalene ring system linked to an azulene unit.
  • Two similar, non-planar molecules were observed in the asymmetric unit, with root-mean-square deviations of approximately 0.091 Å.
  • A significant dihedral angle of 49.60° was found between the molecular planes, with internal dihedral angles between the naphthalene and azulene systems being around 6°.
  • The crystal structure displays a herringbone packing arrangement, stabilized by C-H⋯π interactions.

Conclusions:

  • The detailed crystal structure provides a fundamental understanding of this naphthalene-azulene conjugate.
  • The observed non-planarity and specific dihedral angles influence the molecule's electronic properties.
  • The herringbone packing and C-H⋯π interactions dictate the solid-state properties and potential for material applications.