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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

3.3K
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...
3.3K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.7K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.7K
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

3.9K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
3.9K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.1K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.1K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

8.2K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
8.2K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

9.6K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
9.6K

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Bis[2,3-bis-(thio-phen-2-yl)pyrido[3,4-<i>b</i>]pyrazine]-silver(I) perchlorate methanol disolvate.

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Poly[(μ-2,3-diethyl-7,8-di-methyl-quinoxaline-κ<sup>2</sup><i>N</i>:<i>N</i>)(2,3-diethyl-7,8-di-methyl-quinoxaline-κ<i>N</i>)-μ-nitrato-κ<sup>2</sup><i>O</i>:<i>O</i>'-nitrato-κ<sup>2</sup><i>O</i>,<i>O</i>'-disilver(I)].

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Bis[μ-bis-(pyridin-2-yl)methanone oxime-κ<sup>3</sup><i>N</i>:,<i>N</i>',<i>N</i>'']bis-[di-acetato-κ<sup>2</sup><i>O</i>,<i>O</i>';κ<i>O</i>-zinc(II)].

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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2,3-Di-ethyl-benzo[g]quinoxaline.

Guy Crundwell1, Ashley Leeds2

  • 1Central Connecticut State University, Department of Chemistry & Biochemistry, 1619 Stanley Street, New Britain, CT 06050, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

Researchers synthesized a novel C16H16N2 compound using 3,4-hexanedione and 1,2-diaminonaphthalene. The study details its near-planar fused-ring structure and unique molecular packing, highlighting significant pi-pi stacking interactions.

Keywords:
benzoquinoxalinecrystal structure

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Synthesis of novel organic compounds is crucial for materials science.
  • Understanding molecular structure and packing influences material properties.

Purpose of the Study:

  • To synthesize and characterize a new compound with the molecular formula C16H16N2.
  • To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Chemical synthesis involving 3,4-hexanedione, 1,2-diaminonaphthalene, and ammonium bifluoride (NH4HF2) catalyst.
  • X-ray crystallography to determine the three-dimensional molecular structure and crystal packing.
  • Analysis of bond lengths, bond angles, and deviations from planarity.

Main Results:

  • Successful synthesis of the target C16H16N2 compound.
  • The fused-ring system is nearly planar, with one methyl group deviating significantly from the plane.
  • Molecules exhibit a distinctive criss-cross packing motif in space group I, stabilized by aromatic pi-pi stacking interactions (shortest centroid-centroid separation = 3.5805 Å).

Conclusions:

  • The study provides a detailed structural characterization of a novel organic compound.
  • The observed molecular packing and pi-pi stacking suggest potential applications in materials science.
  • Further research could explore the electronic or optical properties influenced by this specific crystal structure.