Related Experiment Video
Updated: Jun 1, 2026
11:51
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
4-(6-Quinolyl-oxymeth-yl)benzonitrile
Min Min Zhao1, Yong Hua Li, De Hong Wu
1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China.
Summary
A novel quinoline derivative was synthesized and its crystal structure analyzed. The compound exhibits unique intermolecular interactions, including C-H⋯π and C-H⋯N bonds, influencing its crystal packing.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
- Understanding intermolecular interactions is crucial for designing functional organic materials.
Purpose of the Study:
- To synthesize a novel quinoline derivative containing a benzonitrile moiety.
- To elucidate the crystal structure and analyze the intermolecular interactions of the synthesized compound.
Main Methods:
- Ether synthesis utilizing quinolin-6-ol and 4-(bromo-meth-yl)benzonitrile.
- Single-crystal X-ray diffraction analysis to determine the crystal structure.
Main Results:
- Successful synthesis of the target compound C(17)H(12)N(2)O.
- The crystal structure revealed a dihedral angle of 47.52° between the phenyl and quinoline rings.
- Intermolecular C-H⋯π interactions and weak C-H⋯N hydrogen bonds were identified as key stabilizing forces.
Conclusions:
- The synthesized quinoline derivative possesses a distinct molecular conformation.
- The crystal packing is governed by a combination of π-π stacking and hydrogen bonding.
- This study provides insights into the structure-property relationships of quinoline-based compounds.
Related Concept Videos
00:59Reactions at the Benzylic Position: Oxidation and Reduction
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.
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
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.
01:37NMR Spectroscopy of Benzene Derivatives
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 constants depend...
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...
01:11Reactions at the Benzylic Position: Halogenation
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.