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Updated: Jun 1, 2026
09:58
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Dimethyl 2-(2-quinolylmeth-yl)malonate.
Summary
This study details the crystal structure of a novel quinoline derivative. Its molecular structure features coplanar quinoline and malonate groups, with malonate chains at right angles, stabilized by hydrogen bonds into dimers.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Quinoline derivatives are important scaffolds in medicinal chemistry and materials science.
- Understanding the solid-state structure of organic molecules is crucial for predicting their properties and designing new compounds.
- Malonate esters are versatile synthetic intermediates with diverse applications.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(15)H(15)NO(4).
- To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
- To investigate the role of non-classical hydrogen bonding in crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Crystallographic data were collected and refined to high precision.
- Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
Main Results:
- The quinoline ring system and one malonate side chain were found to be essentially coplanar (r.m.s. deviation = 0.0297 Å).
- The two malonate side chains exhibited a near-orthogonal orientation relative to each other (89.68(8)°).
- Crystal packing is characterized by the formation of dimers through weak, non-classical intermolecular C-H⋯O hydrogen bonds around inversion centers.
Conclusions:
- The determined crystal structure provides fundamental insights into the solid-state behavior of this quinoline derivative.
- The observed coplanarity and orthogonal orientation of the malonate groups influence the molecule's overall conformation.
- Intermolecular hydrogen bonding plays a significant role in stabilizing the crystal lattice and directing molecular assembly.
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