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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
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...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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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,...
4.4K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
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...
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UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

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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...
30.7K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
7.6K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Anthracene-1,4,9,10-tetra-one.

Chitoshi Kitamura1, Takeshi Kawase2

  • 1Department of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
PubMed
Summary

This study details the crystal structure of C14H6O4, revealing non-planar molecular conformations due to peri-repulsion. The arrangement features intermolecular interactions leading to a unique herringbone crystal packing.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding molecular conformation and crystal packing is crucial for predicting material properties.
  • Anthracene derivatives exhibit diverse structural motifs and intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C14H6O4.
  • To investigate the conformational preferences and intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • Analysis of bond distances, angles, and non-covalent interactions (C-H⋯O, π-π stacking) was performed.

Main Results:

  • The asymmetric unit contains three independent molecules (A, B, C) of C14H6O4.
  • Molecules exhibit non-planar conformations due to peri-repulsion between oxygen atoms.
  • Disordered carbonyl oxygen atoms were observed in molecule C.
  • Intermolecular C-H⋯O and π-π interactions facilitate a herringbone crystal arrangement.

Conclusions:

  • The crystal structure of C14H6O4 is characterized by non-planar molecules and a distinctive herringbone packing.
  • Intramolecular peri-repulsion influences molecular geometry.
  • Intermolecular interactions dictate the overall crystal architecture.