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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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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...
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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,...
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Facile Preparation of 4-Substituted Quinazoline Derivatives
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5-Nitro-2,3-bis-(thio-phen-2-yl)quinoxaline.

Jorge F de Freitas1, Shayne Brown1, James S Oberndorfer1

  • 1Department of Chemistry & Biochemistry, Central Connecticut State University, 1619 Stanley Street, New Britain, CT 06053, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

A novel quinoxaline derivative was synthesized using a condensation reaction. Structural analysis revealed specific dihedral angles between the quinoxaline core and its thienyl rings, indicating a non-planar conformation.

Keywords:
crystal structurequinoxalinethio­phene

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Quinoxaline derivatives are important scaffolds in medicinal chemistry and materials science.
  • Understanding the three-dimensional structure of novel organic compounds is crucial for predicting their properties and applications.

Purpose of the Study:

  • To synthesize a new compound containing quinoxaline and thienyl moieties.
  • To determine the solid-state structure and conformation of the synthesized compound using X-ray crystallography.

Main Methods:

  • Synthesis of the title compound (C16H9N3O2S2) via a condensation reaction.
  • Recrystallization from acetic acid.
  • Single-crystal X-ray diffraction analysis to determine molecular structure and crystal packing.

Main Results:

  • The title compound was successfully synthesized and characterized.
  • X-ray diffraction data revealed the crystal structure.
  • The dihedral angles between the quinoxaline mean plane and the thienyl rings were determined to be 35.16(5)° and 24.94(3)°, indicating significant deviation from planarity.

Conclusions:

  • A novel C16H9N3O2S2 compound featuring quinoxaline and thienyl groups was synthesized.
  • The compound exhibits a non-planar conformation in the solid state, with defined dihedral angles between the ring systems.
  • These structural findings provide a basis for further investigation into the compound's potential applications.