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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
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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.
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Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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2,3-Dimeth-oxy-5,12-tetra-cenequinone.

Chitoshi Kitamura1, Naoki Akamatsu, Akio Yoneda

  • 1Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a C(20)H(14)O(4) compound, revealing its near-planar geometry and intermolecular interactions. The molecules form slipped face-to-face stacks, crucial for understanding its solid-state properties.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the solid-state structure of organic molecules is essential for predicting their properties.
  • Polycyclic aromatic hydrocarbons with quinone functionalities are of interest due to their electronic properties.

Purpose of the Study:

  • To elucidate the crystal structure and intermolecular interactions of the title compound C(20)H(14)O(4).
  • To analyze the planarity of the molecule and the arrangement of methoxy groups.
  • To investigate the packing motifs and intermolecular forces governing the solid-state structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
  • Intermolecular interactions, including C-H⋯O and π-π stacking, were identified and quantified.

Main Results:

  • The molecule C(20)H(14)O(4) exhibits an approximately planar core structure with minor deviations.
  • Methoxy groups show slight twists (3.3° and 5.6°) relative to the tetra-cenequinone plane.
  • Molecules arrange in slipped face-to-face stacks along the b axis, with an inter-planar distance of 3.407 Å, driven by π-π interactions.
  • All oxygen atoms participate in intermolecular C-H⋯O interactions.

Conclusions:

  • The crystal structure of C(20)H(14)O(4) is characterized by a nearly planar core and specific methoxy group orientations.
  • Intermolecular C-H⋯O interactions and π-π stacking play significant roles in stabilizing the observed crystal packing.
  • The slipped stacking arrangement suggests potential for interesting electronic or optical properties in the solid state.