Related Experiment Video
Updated: Jun 1, 2026
11:51
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
2-Meth-oxy-quinoline-3-carbaldehyde
Summary
This study details the crystal structure of a quinoline derivative, C(11)H(9)NO(2). Molecules form dimers through hydrogen bonds and are further linked by pi-pi interactions, revealing key intermolecular forces in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the intermolecular interactions of organic molecules is crucial for predicting and controlling their solid-state properties.
- Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
- Detailed structural analysis provides insights into molecular packing and reactivity.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(11)H(9)NO(2).
- To investigate the role of hydrogen bonding and pi-pi interactions in the molecular assembly.
- To provide a foundation for understanding structure-property relationships in related quinoline systems.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Analysis of bond lengths, bond angles, and intermolecular distances.
- Identification and characterization of hydrogen bonding and pi-pi stacking interactions.
Main Results:
- The quinoline ring system in C(11)H(9)NO(2) exhibits near planarity.
- Methoxy and aldehyde groups are nearly coplanar with the quinoline core.
- Molecules self-assemble into centrosymmetric dimers via C-H...O hydrogen bonds.
- These dimers are further organized by pi-pi interactions between aromatic rings, with a centroid-centroid distance of 3.639 Å.
Conclusions:
- The crystal structure of C(11)H(9)NO(2) is characterized by a combination of hydrogen bonding and pi-pi interactions.
- These intermolecular forces dictate the observed molecular packing and supramolecular architecture.
- The findings contribute to the understanding of crystal engineering principles for quinoline-based compounds.
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...
01:17Phase II Reactions: Methylation Reactions
Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.