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Related Concept Videos

Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

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...
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).
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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...
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...

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Related Experiment Video

Updated: Jun 5, 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

1,4-Bis(chloro-meth-yl)naphthalene.

Muhammad Ilyas Tariq, M Nawaz Tahir, Ishtiaq Hussain

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the molecular structure of C(12)H(10)Cl(2), revealing specific torsion angles and π-π interactions that drive crystal packing in naphthalene derivatives.

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    Published on: July 17, 2020

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding molecular conformation and intermolecular forces is crucial for predicting material properties.
    • Naphthalene derivatives are important building blocks in various chemical applications.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of a specific dichlorinated naphthalene molecule.
    • To analyze the conformational preferences and packing motifs in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of torsion angles and non-covalent interactions, including π-π stacking, was performed.

    Main Results:

    • The molecule C(12)H(10)Cl(2) exhibits specific torsion angles around the C(m)-C(r) bonds: -104.1(4)° and -101.9(4)°.
    • Molecules are arranged in stacks facilitated by π-π interactions between naphthalene ring systems, with a centroid-centroid distance of 3.940 Å.

    Conclusions:

    • The determined torsion angles provide insights into the conformational flexibility of the molecule.
    • The observed π-π stacking interactions are key to the observed crystal packing and influence material properties.