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Related Concept Videos

IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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).
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range. Consider...
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...
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.

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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

2,7-Bis(4-acetyl-phen-oxy)naphthalene.

Kosuke Nakaema, Masahiro Imaizumi, Keiichi Noguchi

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    This study details the asymmetrical molecular conformation of a novel organic compound, C(26)H(20)O(4). Key findings include specific twisting of acetyl-phenyl groups and evidence of C-H⋯O hydrogen bonding and π-π stacking interactions.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding molecular conformation is crucial for predicting material properties.
    • Naphthalene derivatives are widely studied for their electronic and optical applications.
    • Intermolecular interactions significantly influence crystal packing and bulk material behavior.

    Purpose of the Study:

    • To elucidate the solid-state structure and conformation of the title compound, C(26)H(20)O(4).
    • To investigate the nature and extent of intermolecular interactions, including hydrogen bonding and π-π stacking.
    • To provide a detailed crystallographic analysis of this novel organic molecule.

    Main Methods:

    • Single-crystal X-ray diffraction at 193 K.
    • Analysis of molecular geometry and conformation.

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

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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

    Published on: July 17, 2020

  • Identification and quantification of intermolecular interactions (C-H⋯O, π-π stacking).

    • Main Results:

    • The compound exhibits an asymmetrical conformation with significant twisting of the 4-acetyl-phenyl groups relative to the naphthalene core.
    • Inter-planar angles between benzene and naphthalene ring systems are 68.71° and 74.01°.
    • C-H⋯O hydrogen bonds and π-π stacking interactions (centroid-centroid distance 3.5938 Å, interplanar distance 3.517 Å) were identified.

    Conclusions:

    • The determined crystal structure reveals a unique asymmetrical conformation driven by steric and electronic factors.
    • The presence of both hydrogen bonding and π-π stacking suggests potential for ordered supramolecular assembly.
    • This detailed structural information is vital for the design of new materials based on naphthalene derivatives.