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Facile Preparation of 4-Substituted Quinazoline Derivatives

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Published on: February 15, 2016

2-Meth-oxy-quinoline-3-carbaldehyde.

K Chandraprakash, P Ramesh, K Ravichandran

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

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.

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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.