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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 property is crucial in...

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Updated: May 27, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

8-(Naphthalen-1-yl)quinoline.

Godwin Kanu, Roger A Lalancette, Dale E Vitale

Acta Crystallographica. Section E, Structure Reports Online

|November 8, 2011

Summary

This study reveals a unique crystal structure for a C19H13N molecule, featuring alternating homochiral layers of R and S isomers. This arrangement suggests potential for spontaneous resolution in chiral compounds.

Area of Science:

Crystallography
Organic Chemistry
Materials Science

Background:

The title molecule, C19H13N, possesses a complex structure involving linked naphthalene and quinoline ring systems.
Understanding the solid-state arrangement of chiral molecules is crucial for predicting and controlling their properties.

Purpose of the Study:

To elucidate the crystal structure of the C19H13N molecule.
To investigate the potential for spontaneous resolution based on its crystalline arrangement.
To analyze the molecular orientation within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of the crystal packing and molecular orientations was performed.

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Green Synthesis of Quinoline-Based Ionic Liquid

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

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Last Updated: May 27, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Green Synthesis of Quinoline-Based Ionic Liquid

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Main Results:

The angle between the mean planes of the naphthalene and quinoline systems was determined to be 68.59(2)°.
The crystal structure exhibits alternating homochiral layers of R and S isomers.
Molecules within each layer share a common orientation of their major axes and parallel ring systems, with this orientation alternating between adjacent layers.

Conclusions:

The observed crystal packing, with alternating homochiral layers and specific molecular orientations, provides a structural basis for the compound's potential for spontaneous resolution.
This detailed structural analysis offers insights into the self-assembly mechanisms of chiral organic molecules.