Related Experiment Video
Updated: Jun 1, 2026
11:51
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
2-[(E)-4-Quinolylmethyl-ideneamino]-phenol
Summary
The crystal structure of C(16)H(12)N(2)O reveals a significant dihedral angle between its aromatic systems. Molecular packing is reinforced by specific intra- and inter-molecular hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular interactions is crucial in crystal engineering.
- Hydrogen bonding plays a key role in stabilizing crystal structures.
- Aromatic ring systems influence molecular conformation and packing.
Purpose of the Study:
- To elucidate the crystal structure of the title compound C(16)H(12)N(2)O.
- To analyze the dihedral angle between aromatic systems.
- To investigate the role of hydrogen bonding in molecular packing.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Analysis of bond lengths, bond angles, and torsion angles.
- Identification and analysis of hydrogen bonding interactions (O-H⋯N and C-H⋯N).
Main Results:
- The dihedral angle between the two aromatic ring systems was determined to be 68.54(5)°.
- Intra- and inter-molecular O-H⋯N hydrogen bonds were identified.
- Intra-molecular C-H⋯N hydrogen bonds were also observed, contributing to stability.
Conclusions:
- The crystal structure of C(16)H(12)N(2)O is characterized by a notable dihedral angle between its aromatic moieties.
- The molecular packing is significantly stabilized by a combination of intra- and inter-molecular hydrogen bonding interactions.
- These findings contribute to the understanding of structure-property relationships in organic crystalline materials.
Related Concept Videos
01:17Oxidation 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...
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...
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
02:36Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
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 para position.
01:10Radical Chain-Growth Polymerization: Overview
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...