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Related Concept Videos

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 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...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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.
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...

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Related Experiment Video

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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6,11-Dihydroxy-naphthacene-5,12-dione.

Masaaki Tomura, Hiroyuki Yamaguchi, Katsuhiko Ono

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

    This study details the crystal structure of a C18H10O4 compound, revealing a planar, centrosymmetric molecule. Intramolecular and intermolecular hydrogen bonds influence its structure and packing arrangement.

    Area of Science:

    • Crystallography
    • Molecular structure analysis
    • Supramolecular chemistry

    Background:

    • Understanding molecular geometry and intermolecular interactions is crucial in materials science.
    • Hydrogen bonding plays a significant role in the self-assembly and properties of organic compounds.
    • C18H10O4 represents a class of molecules with potential applications in organic electronics or pharmaceuticals.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the title compound, C18H10O4.
    • To investigate the nature and role of hydrogen bonding in the molecular and crystal structure.
    • To characterize the packing arrangement of the molecules in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.

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    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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    Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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    Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

    Published on: September 18, 2016

  • Analysis of bond lengths and angles provided insights into molecular geometry.
  • Intermolecular and intramolecular interactions, including hydrogen bonds, were identified and analyzed.

    • Main Results:

    • The C18H10O4 molecule was found to be planar and centrosymmetric.
    • A notably long phenolic O-H bond (1.19(9) Å) was observed, participating in an intramolecular hydrogen bond.
    • Molecules adopt a herringbone packing motif, stabilized by intermolecular C-H⋯O hydrogen bonds (2.73–2.77 Å).

    Conclusions:

    • The crystal structure of C18H10O4 is characterized by planarity, centrosymmetry, and significant hydrogen bonding.
    • Intramolecular hydrogen bonding influences the local conformation around the phenolic hydroxyl group.
    • Intermolecular hydrogen bonds dictate the observed herringbone packing, contributing to the overall crystal architecture.